Vacation Rentals with Air Conditioning in Santa Barbara, Italy
Results 201 - 220 of 311
Villa Chiara
Independent Vacation rental with private pool, A/C, WIFI, TV, terrace, panoramic view, near Cortona
- 8
- 3
- 3
Description
Conveniently located 890 m (2904 ft) from Il Castagno, Italy and only 5 km (3 mi) from Cortona. Holiday home Villa Chiara is a nice stone building (120 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to eight people comfortably in three bedrooms with three bathrooms.
Your Experience
Upon arrival at Villa Chiara you’ll find a nice clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Dining with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 5 km (3 mi), Montepulciano 29 km (18 mi), Arezzo 33 km (20 mi), Perugia 48 km (30 mi) and Assisi 65 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 123 km (76 mi), Viareggio 216 km (134 mi), Forte Dei Marmi 223 km (139 mi), Rome 211 km (131 mi), Venice 373 km (231 mi) and Milan 416 km (258 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 136 km (85 mi), Pisa (psa) 197 km (122 mi), Bologna (blq) 217 km (135 mi), Roma Ciampino (cia) 220 km (137 mi) and Roma Fiumicino (fco) 233 km (145 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a fun way to spend time with friends and family while learning the secrets needed to prepare delicious Tuscan meals when you return home. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will schedule the meal based on your preferences and dietary needs. The chef will offer suggestions for the various courses and the wine. Ask for more details and the supplemental costs.
Tours - The owner can schedule custom tours for your group. To learn about the tours offered, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Inquire for more details, including the extra cost and how to schedule this service.
Baby Sitting - A babysitter can be arranged at Villa Chiara. If you're traveling with kids and would like some alone time, talk to the owner directly about this option after arriving.
Villa Chiara
Book your vacation for the period from 30 May 2026 to 06 June 2026 and save 40% (minimum 7 nights). Offer valid until 28 May 2026.
Villa Montepulciano Vineyard
Unique independent accommodation with private pool, A/C, WIFI, hot tub, TV and patio
- 10
- 4
- 3
Description
Villa Montepulciano Vineyard and Pool Retreat is located 2 km (1 mi) from Montepulciano, Italy and only 34 km (21 mi) from Montalcino in the tourist area "Orcia Valley". Villa Montepulciano Vineyard and Pool Retreat is a beautiful vacation rental (300 sq m) with private pool, WiFi internet and air conditioning. The property can sleep up to ten guests comfortably in four bedrooms with three bathrooms.
What to Expect
Upon arrival you’ll find a lovely clean well-maintained property perfect for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of sightseeing. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people.
Visit the Area
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montalcino 34 km (21 mi), Cortona 40 km (25 mi), Arezzo 52 km (32 mi), Siena 68 km (42 mi) and Perugia 77 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 125 km (78 mi), Viareggio 211 km (131 mi), Forte Dei Marmi 218 km (136 mi), Rome 183 km (114 mi), Venice 364 km (226 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 17:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 June - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 126 km (78 mi), Pisa (psa) 192 km (119 mi), Roma Ciampino (cia) 192 km (119 mi), Roma Fiumicino (fco) 205 km (127 mi) and Bologna (blq) 216 km (134 mi).
Villa Montepulciano Vineyard
Book your vacation for the period from 02 April 2026 to 19 December 2026 and save 15% (minimum 2 nights).
Villa Eleonora
Pretty independent villa with WIFI, A/C, private pool, TV, patio, panoramic view, near Cortona
- 8
- 4
- 5
Description
Conveniently located 2 km (5121 ft) from Il Castagno, Italy and only 6 km (4 mi) from Cortona. Villa Eleonora is a nice holiday home (170 sq m) with WiFi internet, air conditioning and private pool. The property can accommodate up to eight guests comfortably in four bedrooms with five bathrooms.
What to Expect
When you arrive you’ll find a beautiful clean well-maintained property with views of the mountains and the hills ideal for a peaceful vacation in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of sightseeing. For your pleasure, on the grounds there is a patio and barbecue grill. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the beautiful Tuscan weather.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 6 km (4 mi), Montepulciano 30 km (19 mi), Arezzo 33 km (21 mi), Perugia 49 km (30 mi) and Assisi 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 124 km (77 mi), Viareggio 217 km (135 mi), Forte Dei Marmi 224 km (139 mi), Rome 212 km (132 mi), Venice 373 km (232 mi) and Milan 417 km (259 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Eleonora. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 137 km (85 mi), Pisa (psa) 198 km (123 mi), Bologna (blq) 218 km (136 mi), Roma Ciampino (cia) 221 km (138 mi) and Roma Fiumicino (fco) 234 km (145 mi).
Additional Services
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the exact tour and number of people.
Baby Sitting - A babysitter can be scheduled at Villa Eleonora. If you're traveling with kids and would like some alone time, talk to the owner directly about this option after arriving.
Villa Eleonora
Book your vacation for the period from 28 March 2026 to 02 May 2026 and save 10% (minimum 5 nights). Offer valid until 02 May 2026.
Villa del Castagno
Unique private holiday home with WIFI, A/C, private pool, TV, patio, panoramic view, near Cortona
- 7
- 3
- 3
Description
Conveniently located 1 km (4118 ft) from Il Castagno, Italy and only 6 km (4 mi) from Cortona. Property Villa Del Castagno is a lovely stone building (190 sq m) that includes private pool, WiFi internet and air conditioning. The property can accommodate up to seven guests comfortably in three bedrooms with three bathrooms.
The Experience
Upon arrival you’ll find a nice clean well-maintained property with views of the hills ideal for a peaceful holiday in Tuscany. For your enjoyment you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of visiting museums. Also available outdoors are a barbecue grill and patio. Sharing a meal with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to seven people. Dine 'al fresco' like a real Tuscan, the fully furnished patio is the ideal setting to enjoy food, family and the nice Tuscan weather.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 6 km (4 mi), Montepulciano 30 km (18 mi), Arezzo 33 km (21 mi), Perugia 48 km (30 mi) and Assisi 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 130 km (81 mi), Viareggio 217 km (135 mi), Forte Dei Marmi 224 km (139 mi), Rome 212 km (132 mi), Venice 373 km (232 mi) and Milan 416 km (259 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 137 km (85 mi), Pisa (psa) 198 km (123 mi), Roma Ciampino (cia) 221 km (137 mi), Bologna (blq) 225 km (140 mi) and Roma Fiumicino (fco) 234 km (145 mi).
Special Services
Cooking Lessons - If you're interested in learning more about Tuscan cooking, ask about the cooking lessons that can be scheduled at the property. It's a pleasant way to spend time with friends and family while discovering the techniques required to master Tuscan cuisine. For more details and the additional cost, please contact us.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours available, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service upon arrival.
Villa Delle Fragole
Villa Recanati, Val D'Orcia, Private Pool, Jacuzzi
Independent House with hot tub, WIFI, A/C, private pool, TV, terrace, pets allowed, panoramic view
- 14
- 6
- 6
Description
Property Villa Recanati, Val D'orcia, Private Pool, Jacuzzi is a lovely property (500 sq m) that includes air conditioning, hot tub and WiFi internet. The property can sleep up to 14 people comfortably in six bedrooms with six bathrooms. Villa Recanati, Val D'orcia, Private Pool, Jacuzzi is located 18 km (11 mi) from Montepulciano, Italy and only 45 km (28 mi) from Montalcino.
The janitor resides in the annex and takes care of guests only when requested or needed. He can provide guests with their privacy, but at the same time ensure timely assistance in case of need.
What to Expect
After arriving you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills perfect for a relaxing vacation in Tuscany. After a busy day of visiting museums, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. For your pleasure, on the grounds there is a hot tub, playground and barbecue grill. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montalcino 45 km (28 mi), Cortona 52 km (32 mi), Perugia 58 km (36 mi), Arezzo 62 km (38 mi) and Assisi 77 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 134 km (83 mi), Viareggio 218 km (136 mi), Forte Dei Marmi 228 km (142 mi), Rome 168 km (104 mi), Venice 374 km (232 mi) and Milan 422 km (262 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Recanati, Val D'orcia, Private Pool, Jacuzzi. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 April - 1 November (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 140 km (87 mi), Roma Ciampino (cia) 177 km (110 mi), Roma Fiumicino (fco) 189 km (118 mi), Pisa (psa) 202 km (126 mi) and Bologna (blq) 226 km (141 mi).
More Services
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours offered, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Villa Recanati, Val D'orcia, Private Pool, Jacuzzi
- 12
- 6
- 7
Description
Property Summary
This independent farmhouse vacation rental spans 450 square meters and is nestled on the slopes of Monte Cappuccini, which divides the Val d'Orcia from the Val di Chiana in Montepulciano, Italy. The property has been recently restored with meticulous attention to interior decoration, featuring authentic antique furniture, traditional terracotta ceilings, and antique parquet floors that embody true Tuscan style. You will find this detached residence offers both relaxation and easy access to explore the surrounding vineyards and olive groves that characterize the hills and plains of the region. The property provides convenient parking on site and complimentary Internet Wifi connection throughout your stay, ensuring you remain connected while enjoying the tranquility of the Tuscan countryside.
Outdoors
The property features a private non-heated swimming pool measuring 8 by 16 meters with a depth of 1.4 meters, available for your enjoyment from May 15 to September 30. You will discover a natural pond within the expansive garden, which is beautifully bordered by woods and olive groves, creating a serene environment for outdoor relaxation. A gazebo equipped with tables and chairs is positioned directly in front of the kitchen, offering an ideal space for al fresco dining while taking in the picturesque Tuscan landscape. Pool towels are provided for your convenience, and the entire property is fenced, ensuring privacy and security during your stay.
Unit Layout
The residence accommodates up to 12 guests across 6 bedrooms and 7 bathrooms, distributed thoughtfully over two levels. On the ground floor, you will find a reading and television lounge, a large kitchen seamlessly connected to a very spacious dining room, and 2 suites, each featuring a private bathroom with bathtub and an additional reading living room. An extra bathroom with laundry facilities is also located on this level. The first floor comprises 2 double bedrooms, each with a private bathroom equipped with a shower, and 2 junior suites, each also offering a private bathroom with shower. The entire villa showcases exceptional furnishings, including furniture dating from the 1800s combined with contemporary design elements. Upon request, the property can accommodate up to 17 guests for an additional cost, utilizing a double sofa bed and a single sofa bed in the ground floor suite, as well as single pouf beds in both junior suites on the first floor. A crib is also available upon request.
Amenities Included
Your accommodation includes comprehensive climate control with Air Conditioning available throughout the villa and Heat Available during the permitted season. The kitchen is fully equipped with modern conveniences including a Dishwasher, Microwave, oven, toaster, coffee maker, and American coffee maker to facilitate meal preparation. Entertainment options feature Television with Satellite TV offering English channels available for your viewing pleasure. The interior Fireplace adds warmth and ambiance to the living spaces. Practical amenities include a Washing Machine, iron and ironing board to ensure comfort during extended stays. Outdoor cooking enthusiasts will appreciate the Barbecue facilities available on the property.
Other Information
Check-in begins at 3:00 PM on Saturday by appointment, and check-out is required by 9:00 AM. You must provide arrival details at least 2 weeks prior to your arrival date. Upon arrival at the property, you are required to pay a security deposit in cash to the property representative in the amount of 800 euro, which will be returned prior to departure, net of any accidental damage to the property. All guests must provide a photocopy of their passport and sign a form for the local authorities upon arrival. The property is within walking distance from the city center. Heating in Italy is allowed by law from November 1 to April 1, with some exceptions for extreme weather conditions. Please note that fans are not usable. Kitchen services, if desired, must be arranged at least 2 months before arrival. An arrival fee applies if you arrive outside the indicated hours. Occasionally you may hear some noise coming from the underlying spa. Animals are not allowed on the property. Baby beds and child chairs are available with an extra cost.
Distances and Attractions
The farmhouse is situated in an enviable location that allows you to explore both the Val d'Orcia and the Val di Chiana regions. The surrounding area is characterized by rolling hills covered with vineyards and olive groves, offering scenic routes for leisurely walks or cycling excursions. The property's position on Monte Cappuccini provides easy access to numerous attractions in the Montepulciano area, including local wineries that offer tours and tastings. The historic city center is within walking distance, where you can discover traditional restaurants, shops, and cultural landmarks that showcase the authentic character of Tuscany.
Costs & Services
Included services
- Pool towels
- Free parking on site
Extra costs
- Stay tax: 1 euro per person per day
- Tourist tax for adults or children: 100 euro per week
- Cleaning: 350 euro per week
- Air conditioning: Extra charge
- Heating: According to consumption, approximately 80 to 100 euro per day
- Gas: Based on consumption at market value
- Arrival fee: To be paid upon arrival for arrivals outside indicated hours
- Baby bed available: Extra cost
- Child chair available: Extra cost
On request
- Dog: 100 euro per week
- Cooking service: 70 euro per person
- Cooking classes: 120 euro per person
- Breakfast service: 25 euro per person
- Housekeeping: 25 euro per hour
- Pre-provided villa: 80 euro plus the cost of groceries
- Winery tours: 40 euro per person
- Bicycles: Available by reservation only
- Ping-pong table: Available by reservation only
- Catering services: Breakfast, on the road lunch, brunch in the villa, traditional dinner, gourmet dinner Podere Monti
- 16
- 7
- 9
Description
Conveniently located 8 km (5 mi) from Montepulciano, Italy in the tourist area "Orcia Valley" and only 36 km (22 mi) from Montalcino. Villa Pianoia is a beautiful holiday home (450 sq m) with air conditioning, WiFi internet and hot tub. The property can sleep up to 16 guests comfortably in seven bedrooms with nine bathrooms.
It is a luxury historic villa that has recently been renovated.
In case of reduced occupancy of 12 guests or fewer, some rooms will remain closed.
The Experience
Upon arrival you’ll find a nice clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. For your pleasure you will find a private garden where you can relax while enjoying a nice cold beverage after a busy day of shopping. A real benefit of renting a home, instead of multiple hotel rooms, is the ability to relax after a busy day of sightseeing with family and friends. Enjoy a meal together along with some local wine to finish the day. For your pleasure, on the grounds there is a patio, barbecue grill and hot tub. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 16 people.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montalcino 36 km (22 mi), Cortona 39 km (24 mi), Arezzo 58 km (36 mi), Siena 73 km (46 mi) and Perugia 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 130 km (81 mi), Viareggio 217 km (135 mi), Forte Dei Marmi 224 km (139 mi), Rome 189 km (117 mi), Venice 370 km (230 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 16:00 - 21:00
Check-Out Time: 08:00 - 10:00
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 136 km (84 mi), Roma Ciampino (cia) 190 km (118 mi), Pisa (psa) 198 km (123 mi), Roma Fiumicino (fco) 200 km (124 mi) and Bologna (blq) 222 km (138 mi).
Special Services
Cooking Lessons - If you're interested in learning more about Tuscan cooking, inquire about the cooking lessons that can be scheduled at the property. It's a fun way to spend time with friends and family while discovering the techniques needed to master Tuscan cuisine. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will organize the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Inquire for more details and the supplemental costs.
Tours - The owner can organize custom tours for your group. To learn about the tours offered, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Villa Pianoia
Book 60 days or less before the arrival date and receive a 20 % discount off the published rental rates.
This Offer is valid only for stays of 4 nights minimum and can not be combined with any other special offers.
- 10
- 4
- 4
Description
Property Summary
Villa il Guscio is an idyllic Tuscan retreat surrounded by stunning landscapes and tranquility. The vacation rental boasts a private fenced garden spanning 1,000 square meters, complete with a seasonal outdoor swimming pool (12x6 meters, depth 140-250 cm) available from May 3rd to September 27th. Enjoy alfresco dining with a barbecue area and outdoor shower. Indoors, you'll find amenities like a fitness room, billiard table, and table football. Parking is available on the premises, and the property offers Internet WiFi access.
Outdoors
The villa's beautiful outdoor spaces beckon adventure and relaxation. Immerse yourself in the Tuscan countryside with hiking trails on the slopes of Pratomagno, offering breathtaking nature walks and spectacular views. Just an example, the sandy beaches of Versilia and Maremma are 150 kilometers away, perfect for a scenic coastal excursion.
Other Information
For added convenience, a cook is available upon request (extra charge). Heating is available from November 1st to April 7th, with costs to be paid on-site. The property is serviced by a gardener responsible for pool maintenance. Nearby, you'll find a grocery store within 900 meters, a supermarket 6 kilometers away, and a restaurant just 300 meters from the villa.
Distances and Attractions
Villa il Guscio is perfectly situated for exploring some of Italy's most beautiful art cities. Within an hour's drive, you can visit Florence (59 km), Siena (63 km), Arezzo (44 km), and Cortona, as well as the charming valleys of Casentino and Val d'Orcia. Nearby attractions include Loro Ciuffenna (3 km), Castelfranco di Sopra (12 km), Gaiole in Chianti (30 km), Greve in Chianti (36 km), Monte San Savino (50 km), and the thermal baths of Rapolano Terme (47 km). The villa is located 7.5 kilometers from the center of Terranuova Bracciolini, Italy. Villa Il Guscio
- 3
- 1
- 1
Description
Property Summary
Le rondini is a modern and comfortable 2-family house in Montepulciano, Italy. It features two apartments, and the property offers amenities such as Internet Wifi and Parking. Enjoy the convenience of being located in the residential district of Cervognano, just 5.2 km from the center of Montepulciano and 16 m from the center of Chiusi.
Outdoors
Unwind in the shared, fenced property that includes a terraced garden and roofed parking at the house. Embrace the elevated position and residential setting, while still being in close proximity to nearby amenities and attractions.
Other Information
To ensure a comfortable stay, the property is equipped with baby equipment included. Please note that the owner lives in the same residence and has a dog. While car access is recommended, the location offers convenience with a shop, grocery, supermarket, and restaurant within a 5 km radius. Additionally, there is a bus stop "Acquaviva" 2.6 km away, a railway station "Montepulciano Scalo" 5.2 km away, and an indoor swimming pool and thermal baths "Chianciano Terme" within a reasonable distance.
Distances and Attractions
Explore the nearby attractions, including the charming towns of Montepulciano (5 km), Pienza (20 km), Cortona (26 km), Montalcino (41 km), and the historic city of Siena (70 km). For a peaceful escape, consider visiting the well-known lakes of Montepulciano (9 km) and Trasimeno (20 km), perfect for a holiday rental or vacation rental getaway. "Just an example." Le Rondini
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Stunning private vacation home with A/C, private pool, WIFI and TV
- 8
- 4
- 5
Description
Holiday home La Dimora del Chianti Dimora: Stunning Tuscan Vill is a lovely property (200 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to eight guests comfortably in four bedrooms with five bathrooms. Conveniently located 5 km (3 mi) from Rietine, Italy in the tourist area "Siena And Surroundings" and only 27 km (17 mi) from Siena.
Your Experience
When you arrive at La Dimora del Chianti Dimora: Stunning Tuscan Vill you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. Regardless of how you spend your days - sightseeing, shopping, visiting museums or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.
Visit the Area
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 27 km (17 mi), Greve In Chianti 33 km (21 mi), Arezzo 52 km (32 mi), San Gimignano 54 km (33 mi) and Montalcino 62 km (38 mi).
Some other major tourist destinations you should consider visiting are: Florence 65 km (41 mi), Viareggio 159 km (99 mi), Forte Dei Marmi 167 km (103 mi), Rome 240 km (149 mi), Venice 316 km (196 mi) and Milan 359 km (223 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 19 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 78 km (49 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 165 km (102 mi), Roma Ciampino (cia) 249 km (155 mi) and Roma Fiumicino (fco) 261 km (162 mi).
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Book now and save 10%. Offer valid until 20 April 2026 and for a minimum stay of 5 nights.
Villa Petrosa: Your Private Escape Overlooking the
Pretty independent villa with WIFI, private pool, A/C, TV, patio and panoramic view
- 10
- 5
- 6
Description
Vacation rental Villa Petrosa: Your Private Escape Overlooking the is a beautiful stone building that includes WiFi internet, air conditioning and private pool. The property can sleep up to ten people comfortably in five bedrooms with six bathrooms. Conveniently located 2 km (1 mi) from Montepulciano, Italy in the tourist area "Orcia Valley" and only 31 km (19 mi) from Cortona.
What to Expect
When you arrive at Villa Petrosa: Your Private Escape Overlooking the you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful holiday in Tuscany. Regardless of how you spend your days - sightseeing, visiting museums, shopping or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Outside you will also find a patio and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people. If you prefer to dine 'al fresco', there is a fully furnished patio where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 31 km (19 mi), Montalcino 38 km (24 mi), Arezzo 50 km (31 mi), Siena 66 km (41 mi) and Perugia 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 123 km (76 mi), Viareggio 209 km (130 mi), Forte Dei Marmi 216 km (134 mi), Rome 189 km (117 mi), Venice 365 km (227 mi) and Milan 409 km (254 mi).
Additional Information
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 128 km (79 mi), Pisa (psa) 190 km (118 mi), Roma Ciampino (cia) 198 km (123 mi), Roma Fiumicino (fco) 211 km (131 mi) and Bologna (blq) 214 km (133 mi).
Special Services
Cooking Lessons - Discover from a local chef the techniques vital to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a fun way to spend time with friends and family while discovering the secrets needed to prepare delicious Tuscan meals when you return home. For more details and the additional cost, please contact us.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your holiday hassle-free after a long trip. Inquire for more details, including the extra cost and how to organize this service.
Villa Petrosa: Your Private Escape Overlooking the
- 15
- 7
- 7
Description
Property Summary
Nestled just 900 metres from the historic centre of Montepulciano, in the heart of Tuscany, Italy, Villa Incanto is an exceptional country house that offers a refined and immersive holiday experience for those seeking elegance, privacy, and natural beauty. The property is composed of 2 stone buildings that have been recently and carefully renovated, blending modern elegant details with traditional architectural character to create an atmosphere of timeless sophistication. Surrounded by a generous yard filled with olive trees, a variety of flowers, and ancient roses, the estate provides a serene and picturesque setting that reflects the very essence of the Tuscan countryside. Guests can enjoy the convenience of on-site parking, stay seamlessly connected with Internet WiFi available throughout all rooms, and take advantage of the private swimming pool, which offers breathtaking views of Montepulciano. A tennis court is also available on the property, adding a further dimension of leisure and recreation to the stay. From the villa, the remarkable skyline of Montepulciano, long celebrated as the pearl of the 15th century and one of the most beautiful cities in the Tuscan region, can be admired in all its splendour.
Outdoors
The outdoor spaces of Villa Incanto are thoughtfully designed to complement the natural landscape and invite guests to fully embrace the beauty of the surrounding environment. The private swimming pool is the centrepiece of the exterior, positioned to capture sweeping views of Montepulciano and equipped with sunbeds and an umbrella to ensure comfort during warm sunny days. A covered gazebo furnished with garden furniture provides a shaded and elegant space for relaxation or informal gatherings in the open air. Several of the suites benefit from direct access to the garden, ensuring an exceptional level of privacy and a seamless connection between the interior living spaces and the lush outdoor surroundings. The garden itself, abundant with olive trees, diverse flowering plants, and ancient roses, creates a tranquil and fragrant atmosphere that enhances every moment spent outdoors. A barbecue is also available, making al fresco dining a natural and pleasurable part of the villa experience.
Other Information
Villa Incanto has been carefully restored to preserve its authentic stone character while introducing a series of refined interior comforts that cater to the expectations of discerning guests. The bathrooms are finished with natural rocks or mosaic detailing, and showers are equipped with hydromassage jets, reflecting the high standard of craftsmanship applied throughout the renovation. Air conditioning is available to ensure comfort during warmer months, while a beautiful working fireplace adds warmth and atmosphere during cooler evenings. The dining room is a particularly striking space, featuring large glass windows that frame extraordinary views of the surrounding landscape, making every meal a visually memorable occasion. Internet WiFi is accessible in all rooms, ensuring guests remain connected throughout their stay without compromising the sense of retreat that the property naturally provides.
Distances and Attractions
Villa Incanto enjoys an outstanding location that places guests within easy reach of some of the most celebrated destinations in central Italy. Montepulciano itself is just 900 metres away, offering an extraordinary concentration of Renaissance architecture, world-renowned Vino Nobile wine, fine dining, and cultural heritage that has earned it the historic title of "the pearl of the 15th century." The villa's position is equally ideal for exploring the wider beauty of both Tuscany and the neighbouring Umbria region, accessible comfortably by car. The nearby town of Chianciano Terme, one of the closest towns to the property, is well known for its celebrated thermal baths and also hosts a train station from which guests can conveniently travel to Florence or Rome, making longer excursions across Italy entirely feasible. Villa Incanto
Montelucci Chianti Agrivilla
Wonderful independent accommodation with A/C, WIFI, private pool, TV, patio and panoramic view
- 14
- 7
- 6
Description
Vacation rental Montelucci Chianti Agrivilla is a nice stone building (400 sq m) that includes WiFi internet, private pool and air conditioning. The property can accommodate up to 14 guests comfortably in seven bedrooms with six bathrooms. Montelucci Chianti Agrivilla is located 560 m (1795 ft) from Montegrossi, Italy and only 30 km (18 mi) from Greve In Chianti in the tourist area "Chianti".
Your Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills and the mountains ideal for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of sightseeing. For your pleasure, on the grounds there is a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Greve In Chianti 30 km (18 mi), Siena 37 km (23 mi), San Gimignano 50 km (31 mi), Arezzo 54 km (34 mi) and Montalcino 74 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 77 km (48 mi), Viareggio 163 km (101 mi), Forte Dei Marmi 171 km (106 mi), Rome 258 km (160 mi), Milan 368 km (229 mi) and Naples 449 km (279 mi).
Additional Information
Check-In Time: 17:00 - 22:00
Check-Out Time: 07:00 - 10:00
Pool Open: 1 May - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 82 km (51 mi), Pisa (psa) 144 km (90 mi), Bologna (blq) 171 km (106 mi), Roma Ciampino (cia) 267 km (166 mi) and Roma Fiumicino (fco) 280 km (174 mi).
More Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while learning the secrets needed to prepare delicious Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Ask for more details and the additional costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours offered, speak to the owner after arriving or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be scheduled by the owner. Ask for more details about the extra cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Montelucci Chianti Agrivilla. Inquire for more details, including the supplemental cost and how to organize this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service upon arrival.
Montelucci Chianti Agrivilla
Villa Ivana - Cortona
Beautiful independent house with WIFI, private pool, hot tub, A/C, TV, patio, near Cortona
- 18
- 9
- 10
Description
Property Villa Ivana - Cortona is a beautiful property (1052 sq m) that includes private pool, WiFi internet and air conditioning. The property can accommodate up to 18 guests comfortably in nine bedrooms with ten bathrooms. Villa Ivana - Cortona is located 2 km (5174 ft) from Ossaia, Italy and only 5 km (3 mi) from Cortona. If playing a round of golf is important while on holiday, you are in luck because there is a course nearby.
In case the Villa is booked at the reduced price (for groups up to 14 people), the Floor 2 will remain closed.
Your Experience
After arriving you’ll find a beautiful clean well-maintained property ideal for a splendid holiday in Tuscany. Regardless of how you spend your days - shopping, visiting museums, sightseeing or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Outside you will also find a barbecue grill and patio.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 5 km (3 mi), Montepulciano 29 km (18 mi), Arezzo 32 km (20 mi), Perugia 48 km (30 mi) and Assisi 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 130 km (81 mi), Viareggio 217 km (135 mi), Forte Dei Marmi 224 km (139 mi), Rome 212 km (132 mi), Venice 373 km (232 mi) and Milan 416 km (259 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 137 km (85 mi), Pisa (psa) 198 km (123 mi), Roma Ciampino (cia) 221 km (137 mi), Bologna (blq) 222 km (138 mi) and Roma Fiumicino (fco) 233 km (145 mi).
Villa Ivana - Cortona
- 18
- 9
- 7
Description
Property Summary
You will discover an extraordinary holiday villa nestled in the gently rolling hills of Monteroni D'arbia, Italy, offering breathtaking views over Siena. This independent residence accommodates up to 18 guests and embodies the warmth and elegance of a private family home through its carefully selected furniture, refined soft furnishings, and thoughtful decorative touches. The property comprises a main building and a separate dependance, both extremely well furnished to ensure your utmost comfort. The estate provides convenient parking and features exceptional recreational facilities including a swimming pool, tennis court, five-a-side football pitch, bowls area, and a dedicated fitness and wellness area with gym and sauna located 50 meters from the villa. The property sits within a working 35-hectare estate that produces olive oil and breeds Cinta Senese pigs, offering you an authentic Tuscan countryside experience.
Outdoors
The outdoor spaces of this remarkable property are designed for both relaxation and recreation. The swimming pool measures 15 x 7.5 meters and operates from 01/05 to 31/10, providing a refreshing retreat during the warmer months. Adjacent to the pool, you will find a recently restored building equipped with a kitchen, barbecue facilities, a bathroom with shower, and a stereo system, creating an ideal setting for outdoor entertaining. The property features a tennis court with a professional red-clay surface, perfect for friendly matches and competitive play. For football enthusiasts, a five-a-side football pitch is available, while those seeking more leisurely pursuits can enjoy a game of bowls. The main building's ground floor opens onto a large internal courtyard where you can dine alfresco, enjoying the stunning Tuscan landscape. A traditional pizza oven adds to the outdoor culinary possibilities, allowing you to create authentic Italian meals in the open air.
Unit Layout
This spacious accommodation comprises 9 bedrooms and 7 bathrooms, comfortably sleeping 18 guests across the main building and dependance. The main building accommodates 14 guests and is arranged over two floors. On the ground floor, you will find a large internal courtyard, a formal dining room, and an expansive living room featuring a fireplace, billiard table, and CD player. A separate room houses satellite television, while the large, fully equipped kitchen includes a fireplace, oven, fridge with ice dispenser, freezer, and dishwasher. A guest toilet and basement cellar complete this level. The first floor presents a generous living room with fireplace, computer, printer, and fax facilities. The sleeping quarters include a double bedroom with en suite bathroom featuring a bathtub, a double bedroom with en suite bathroom offering a shower and Turkish bath, and a magnificent large double suite comprising a studio, dressing room, and en suite bathroom with hydro-massage bathtub. Additionally, you will find a double bedroom, a bathroom with bathtub, another double bedroom, and two double bedrooms sharing an en suite bathroom with bathtub. A winter room with fireplace provides additional living space. The dependance sleeps 4 guests and features a living room, kitchen, and two double bedrooms, each with en suite bathroom equipped with shower.
Amenities Included
Your stay includes comprehensive amenities designed to enhance your comfort and convenience. Air conditioning is installed in each bedroom throughout the property, ensuring pleasant temperatures during warmer months. Entertainment options include satellite TV and television viewing, while multiple fireplaces in the living areas and kitchen provide warmth and ambiance during cooler evenings. The kitchen is fully equipped with modern appliances including a dishwasher and microwave, alongside the oven, refrigerator with ice dispenser, and freezer already mentioned. Outdoor cooking is facilitated by the barbecue located in the pool house. Every room features a stereo system, allowing you to enjoy your favorite music throughout the property. The villa provides internet connection for staying connected during your stay, and laundry facilities are available for your convenience. The wellness area includes a gym and sauna situated 50 meters from the main villa, offering you opportunities for exercise and relaxation.
Other Information
Check-in is available between 3 pm and 7 pm, and check-out is scheduled for 10 am. A competent and helpful housekeeper resides in a room on the ground floor and is available to assist you throughout your stay. The villa can also be rented for a reduced capacity of 14 guests, with pricing available upon request. A security deposit is required upon arrival, which will be returned at the end of your stay minus any costs for damages incurred. The swimming pool is open from 01/05 to 31/10. Upon arrival, a tourist tax may be required according to the regulations of the local municipality.
Distances and Attractions
The property enjoys a magnificent position in the gently rolling hills surrounding Monteroni D'arbia, with spectacular views overlooking the historic city of Siena. The location provides an authentic Tuscan experience within the working 35-hectare estate, where you can witness traditional olive oil production and the breeding of Cinta Senese pigs. The surrounding area offers opportunities to explore charming Tuscan towns, renowned wineries, and the rich cultural heritage of the Siena region.
Costs & Services
Included services
- Consumption of water, gas, and electricity up to 300 kw
- Final cleaning
- Initial supply of linen for rooms and bathrooms with changes every 2 to 3 days
- Cleaning service 4 hours in the morning
- Welcome dinner on arrival
- Air conditioning consumption
Extra costs
- Electricity consumption over 300 kw
- Pool heating: €60 per day
- Pets: €25 per week
- Toddler bed: €30 per week
- Extra bed: €80 per week
- Security deposit: €500
On request
- Breakfast
- Lunch
- Dinner
- Cooking class
- Extra cleaning
- Catering
- Waiting staff
- Driver services
- Massages Villa Giuncheto
- 4
- 2
- 2
Description
Property Summary
Caggiolo is a cozy and comfortable terraced house surrounded by picturesque meadows and vineyards. Nestled in a tranquil countryside setting, it offers a shared swimming pool (fenced and available seasonally from June 1st to September 30th, with designated pool hours from 9 AM to 8 PM), an outdoor shower, a terrace, garden furniture, and parking for two cars. This charming vacation rental provides amenities such as a yard, internet WiFi, and is conveniently located near shops, groceries, supermarkets, restaurants, and bakeries within a 5 km radius.
Outdoors
Enjoy the serene outdoor spaces at Caggiolo. Relax by the shared swimming pool, which is fenced for your safety and available seasonally from June 1st to September 30th, with designated pool hours from 9 AM to 8 PM. An outdoor shower allows you to freshen up after a refreshing dip. Unwind on the terrace, furnished with comfortable garden furniture, and soak in the beautiful surroundings of meadows and vineyards. The property also offers a yard, perfect for enjoying the fresh air and sunshine.
Other Information
Caggiolo is part of a residence comprising 6 houses, ensuring a peaceful and intimate setting. The property is conveniently located 5.5 km from the center of Monteroni d'Arbia and 9 km from the center of Buonconvento. It is well-equipped with baby equipment, making it suitable for families with children. The owner/gardener oversees the pool maintenance, ensuring a clean and well-maintained environment for your enjoyment.
Distances and Attractions
Caggiolo is situated in a prime location, with various amenities and attractions within easy reach. Shops, groceries, supermarkets, restaurants, and bakeries are just 5 km away, while the bus stop "SR 2 Cassia" is 1000 km from the property. The railway station "Monteroni d'Arbia" is conveniently located 5 km away. For those seeking beach time, the sandy beach "Marina di Grosseto" is 80 km away, and the thermal baths "Rapolano Terme" are 39 km from the property. Golf enthusiasts can enjoy an 18-hole golf course located 28 km away, while tennis courts are available 5 km from the property. Walking paths can be accessed directly from the house, stretching 100 m. Nearby attractions include the charming towns of Montalcino (20 km), Siena (20 km), and Pienza (36 km), offering a glimpse into the rich history and culture of the region. Caggiolo
Podere Palazzetto
Unique house with hot tub, A/C, private pool, WIFI, TV, patio, pets allowed, panoramic view
- 8
- 3
- 3
Description
Property Summary
You are considering a comfortable cottage "Podere Palazzetto" in Monteroni D'arbia, Italy. This two-story vacation rental is surrounded by trees and meadows, providing a serene and natural setting. It features amenities such as a swimming pool, yard, internet WiFi, and parking, ensuring a comfortable and convenient stay.
Outdoors
The property boasts a private, fenced garden with a wildlife garden and trees. The highlight is the seasonal swimming pool (3 x 6 m), available from May 1st to October 15th. Enjoy outdoor relaxation with an outdoor shower, hot tub, patio, terrace, and barbecue area. The pool maintenance is taken care of by the owner or gardener.
Other Information
Linen change is available for an additional charge. The property has a 3 km long bumpy motor access road. Amenities nearby include a shop, grocery store, supermarket, restaurant, bus stop "Buonconvento" (8 km), and railway station "Buonconvento" (8 km). For beach enthusiasts, the sandy beach "Follonics" is 94 km away, and the thermal baths "Rapolano Terme" are 23 km away. Please note that a car is recommended for your holiday rental stay. Baby equipment is included, and groups of teenagers are accepted upon request.
Distances and Attractions
Nearby attractions to explore during your stay include Monte Uliveto Maggiore (17 km), Montalcino (18 km), San Quirico d'Orcia (25 km), Siena (28 km), Pienza (35 km), and Montepulciano (46 km). Just an example sentence: "The property is conveniently located near various attractions, allowing you to experience the rich cultural and historical sites of the region." Podere Palazzetto
Il Canto del Maggio
Comfortable apartment with WIFI, pool, A/C, TV, patio, pets allowed and panoramic view
- 6
- 14
- 6
- 6
| Accommodation | ||||
|---|---|---|---|---|
| La Castellana | 2 | 1 | 1 | |
| Canto al Sole | 2 | 1 | 1 | |
| Bellina | 2 | 1 | 1 | |
| Canto alla Luna | 4 | 1 | 1 | |
| Lilla | 2 | 1 | 1 | |
| Cecilia | 2 | 1 | 1 | |
| All 6 Accommodations | 14 | 6 | 6 |
Description
Hospitality, Osteria "Gentile" with veg garden, Cooking School and a stunning infinity pool overlooking the valley: il Canto del Maggio, owned by Simona and her family, isn’t just a place to sleep — it’s a place where you meet a family deeply rooted in this land and in its rhythms.
Here guests are welcomed into six charming units that reflect a rare and authentic form of hospitality: the Albergo diffuso—literally, a ‘scattered hotel’. Developed in Italy, this model revitalizes once-abandoned villages by blending comfort with local tradition in a truly immersive experience- in fact the "borgo" is a shared community between locals that live here permanently, and travelers that was born in the late 1980's.
Our collaboration with this placa was born to promote a network of local chefs, farmers, winemakers, guides, and hospitality professionals — all working together to create meaningful moments that we hope will make your stay one to remember.
My team (I am Tuscany) and I will take care of the accommodation side of your experience — from the moment you book to the day you arrive. Before your stay, we’ll coordinate with you to plan any extra services or personalized experiences, so everything is ready and tailored to your needs before you arrive.
Simona, the soul of this place, will welcome you into her world: her home, her kitchen, around her table, or walking through the vegetable garden — the orto. On the plate, a cuisine that arises spontaneously: the garden decides the menu, and we simply follow its lead.
Together, we can plan special dinners in the garden or by the pool, enjoy breakfast on the terrace or your private patio, and explore much more — from local farmers’ markets and tastings to our favorite go-to places in the area.
Available experiences include:
-Harvesting ingredients directly from the garden and discovering the joy of simple, farm-to-table cooking
-Themed culinary workshops (vegetarian, pastry-making, regional cuisine)
-Activities that immerse you in the natural beauty, culture, and traditions of the area
-Private meals (including breakfast) served anywhere on the property
-Pop-up events hosted by the restaurant or the outdoor kitchen
-Private events and retreats tailored to your needs Il Canto Del Maggio
Special Offer for La Castellana
Book your vacation for the period from 30 March 2026 to 20 December 2026 and save 15% (minimum 7 nights).
Book your vacation for the period from 30 March 2026 to 30 June 2026 and save 10% (minimum 3 nights).
Apartment:
Canto al Sole
Bellina
Canto alla Luna
Lilla
Cecilia
Case Sant'Anna
Independent Property with WIFI, private pool, hot tub, A/C, TV, patio, panoramic view, near Cortona
- 18
- 9
- 8
Description
Case Sant'anna is a beautiful holiday rental (300 sq m) with WiFi internet, air conditioning and hot tub. The property can accommodate up to 18 guests comfortably in nine bedrooms with eight bathrooms. Conveniently located 9 km (6 mi) from Terontola, Italy and only 12 km (8 mi) from Cortona. If playing a round of golf is important while on vacation, you are in luck because there is a course nearby.
Outdoor Jacuzzi, Included in rental price. Open during the same period of the swimming pool.
Please note that the garden is not fenced.
Truffle hunting experience in the proximity of the property, to be requested at the time of booking
What to Expect
After arriving you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property ideal for a peaceful vacation in Tuscany. After a hectic day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day. Outdoors you will also find a hot tub, patio and barbecue grill.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 12 km (8 mi), Montepulciano 26 km (16 mi), Arezzo 36 km (22 mi), Perugia 52 km (32 mi) and Montalcino 60 km (37 mi).
Some other major tourist destinations you should consider visiting are: Florence 124 km (77 mi), Viareggio 211 km (131 mi), Forte Dei Marmi 218 km (135 mi), Rome 206 km (128 mi), Venice 367 km (228 mi) and Milan 410 km (255 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Case Sant'anna. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:30 - 21:00
Check-Out Time: 06:00 - 10:00
Pool Open: 20 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 131 km (82 mi), Pisa (psa) 192 km (119 mi), Roma Ciampino (cia) 215 km (134 mi), Bologna (blq) 218 km (135 mi) and Roma Fiumicino (fco) 228 km (141 mi).
Case Sant'anna
Villa Gaeta
Independent House with private pool, WIFI, A/C, TV, pets allowed, panoramic view, near Montepulciano
- 10
- 5
- 5
Description
Large Tuscan farmhouse dating back to the 15trh century built on the ruins of an ancient convent of the year 1200. This property with a charming inner courtyard, is situated in quiet and panoramic location on a large 100-hectare estate producing olive oil and wine.
This villa has been tastefully restored preserving its original architectural features and ancient materials such as the beautiful terracotta-tiles floors and beamed ceilings and has been converted into a welcoming country-side residence. The interiors are tastefully furnished with some antique pieces.
Outside, guests can enjoy use of a nice garden with a private pool.
The access to the property is via an upaved but well-maintained road of approx. 1,5 km.
Distances: Montefollonico with groceries 4,5 km away, Montepulciano 9 km, Torrita di Siena with general store and Pienza 12 km away, Cortona 40 km, Lake Trasimeno 50 km away, Siena 65 km, Perugia 75 km away, Marina di Grosetto (beaches) 107 km Florence (airport) 110 km away, Pisa (airport) 200 km away, Rome (airport) 215 km away.
At guests’ disposal: furnished garden (lawn) with private swimming-pool (10 x 7 m – depth 1,5 m), barbecue. Guests can also enjoy use of a charming inner courtyard with ancient bread oven and nice loggia. Laundry (accessible from the outside).
This villa provides WI-FI internet connection (free of charge), air-conditioning in all of the bedrooms (with the exception of the one accessible from the courtyard), hairdryers.
Parking with the grounds.
Extra Services: Baby bed and high-chair upon request (free of charge). Maid service by arrangement (€ 15,- / per hour to the paid locally).
Small pets are allowed.
Note: The villa has an outdoor video surveillance system
Please carefully check if there are any extra costs to be paid on site! Villa Gaeta
Book 14 days or less before the arrival date and receive a 20 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
