Top 20 San Sepolcro and Surroundings Villas with Pool
Results 1 - 9 of 9
Palazzo Rosadi
Amazing private vacation rental with WIFI, private pool, A/C, hot tub, TV, patio and panoramic view
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- 6
- 7
In high demand!
Description
Property Palazzo Rosadi is a nice stone building (500 sq m) that includes air conditioning, hot tub and WiFi internet. The property can sleep up to 12 people comfortably in six bedrooms with seven bathrooms. Conveniently located 5 km (3 mi) from Monterchi, Italy in the tourist area "Arezzo And Surroundings" and only 29 km (18 mi) from Arezzo.
Book your dream in Tuscany
Book an all-inclusive dream week in Tuscany from the transfer from the arrival/departure airport; to worry-free tours of Tuscany, enjoying the historical, scenic, and culinary wonders of this magnificent land, all without a care in your exclusive villa. This is available for a minimum of 6 people, fully customizable. Prices starting from Euro 2500 per person plus villa cost depending on the season.
Or enjoy everything included at the Villa, 7 breakfasts, 7 dinners with chef, with the freedom of personal organization starting from Euro 1000 per person, for a minimum of 6 people plus villa cost depending on the season.
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: Arezzo 29 km (18 mi), Cortona 48 km (30 mi), Gubbio 67 km (42 mi), Perugia 70 km (44 mi) and Montepulciano 77 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 119 km (74 mi), Viareggio 205 km (128 mi), Forte Dei Marmi 213 km (132 mi), Rome 244 km (152 mi), Venice 343 km (213 mi) and Milan 405 km (252 mi).
Other services included in the rental price:
Valtiberina tour with the owner
Wine tasting in a local cellar
WELCOME BUFFET ON THE EVENING OF ARRIVAL
Please note that if additional space is needed, it is also possible to book the "Torre del Cielo" villa (for 10 people), located 50m away.
Additional Information
Check-In Time: 16:00 - 18:00
Check-Out Time: 07:00 - 09:30
Pool Open: 1 April - 28 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) 187 km (116 mi), Bologna (blq) 202 km (125 mi), Roma Ciampino (cia) 259 km (161 mi) and Roma Fiumicino (fco) 271 km (169 mi).
Special Services
Tours - Custom tours can be arranged by the owner for your group. For more details about the tours available, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be organized by the owner. Ask for more details about the additional cost.
The nearest town is Monterchi (2.5 km away) and can be reached on foot via a country road.
Palazzo Rosadi
Book your vacation for the period from 04 April 2026 to 04 July 2026 and save 10% (minimum 5 nights).
Villa Vindelbono
Superb independent villa with WIFI, private pool, A/C, TV, patio, pets allowed and panoramic view
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- 3
- 2
Description
Villa Vindelbono is located 4 km (2 mi) from Sansepolcro, Italy and only 39 km (24 mi) from Arezzo in the tourist area "San Sepolcro And Surroundings". Holiday rental Villa Vindelbono is a beautiful stone building that includes WiFi internet, air conditioning and private pool. The property can sleep up to six people comfortably in three bedrooms with two bathrooms.
What to Expect
After arriving you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills perfect 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. For your pleasure, on the grounds there is a patio and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to six people. If you prefer to dine 'al fresco', there is a fully furnished patio where you can enjoy the weather while dining outdoors.
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: Arezzo 39 km (24 mi), Cortona 55 km (34 mi), Gubbio 69 km (43 mi), Urbino 77 km (48 mi) and Perugia 81 km (50 mi).
Some other major tourist destinations you should consider visiting are: Florence 129 km (80 mi), Viareggio 216 km (134 mi), Forte Dei Marmi 223 km (138 mi), Rome 248 km (154 mi), Venice 323 km (201 mi) and Milan 392 km (243 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Vindelbono. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Pool Open: 1 May - 31 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) 135 km (84 mi), Bologna (blq) 186 km (115 mi), Pisa (psa) 197 km (122 mi), Roma Ciampino (cia) 257 km (159 mi) and Roma Fiumicino (fco) 269 km (167 mi).
Special Services
Cooking Lessons - Learn from a local chef the techniques required to master Tuscan cuisine. The owner can arrange to have a chef come to the property for a cooking lesson for any number of people in your group. It's a enjoyable way to spend time with friends and family while discovering the secrets needed to prepare sumptuous 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 delicious meal using local produce? The chef will schedule the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the additional costs.
Tours - The owner can organize 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.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
The garden is fully enclosed.
Up to 3 dogs are permitted. Villa Vindelbono
Torre del Cielo
Wonderful private villa rental with hot tub, private pool, WIFI, A/C, TV, patio and panoramic view
- 10
- 5
- 5
Description
Torre del Cielo is a beautiful stone building (250 sq m) with hot tub, WiFi internet and private pool. The property can sleep up to ten people comfortably in five bedrooms with five bathrooms. Conveniently located 5 km (3 mi) from Monterchi, Italy in the tourist area "Arezzo And Surroundings" and only 29 km (18 mi) from Arezzo. If you enjoy a round of golf while on vacation, then you will be happy to know there is a golf course nearby.
Book your dream in Tuscany
Book an all-inclusive dream week in Tuscany from the transfer from the arrival/departure airport; to worry-free tours of Tuscany, enjoying the historical, scenic, and culinary wonders of this magnificent land, all without a care in your exclusive villa. This is available for a minimum of 6 people, fully customizable. Prices starting from Euro 2500 per person plus villa cost depending on the season.
Or enjoy everything included at the Villa, 7 breakfasts, 7 dinners with chef, with the freedom of personal organization starting from Euro 1000 per person, for a minimum of 6 people plus villa cost depending on the season.
The Experience
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: Arezzo 29 km (18 mi), Cortona 48 km (30 mi), Gubbio 67 km (42 mi), Perugia 70 km (44 mi) and Montepulciano 77 km (48 mi).
Some other major tourist destinations you should consider visiting are: Florence 119 km (74 mi), Viareggio 206 km (128 mi), Forte Dei Marmi 213 km (132 mi), Rome 244 km (152 mi), Venice 343 km (213 mi) and Milan 405 km (252 mi).
Other services included in the rental price:
Valtiberina tour with the owner
Wine tasting in a local cellar
WELCOME BUFFET ON THE EVENING OF ARRIVAL
Please note that if additional space is needed, it is also possible to book the "Palazzo Rosadi" villa (for 12 people), located 50m away.Additional Information
Pool Open: 1 April - 28 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) 187 km (116 mi), Bologna (blq) 202 km (125 mi), Roma Ciampino (cia) 259 km (161 mi) and Roma Fiumicino (fco) 271 km (169 mi).
More Services
Maid Service - Upgrade your holiday with maid service. This service can be scheduled by the owner. Ask for more details about the additional cost.
The nearest town is Monterchi (2.5 km away) and can be reached on foot via a country road.
Torre del Cielo
Book your vacation for the period from 11 April 2026 to 20 June 2026 and save 15% (minimum 5 nights).
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Description
Conveniently located 3 km (2 mi) from Citerna, Italy in the tourist area "San Sepolcro And Surroundings" and only 29 km (18 mi) from Arezzo. Villa Carsuga is a nice stone building (350 sq m) with private pool and WiFi internet. The property can accommodate up to eight guests comfortably in four bedrooms with three bathrooms.
The Experience
When you arrive at Villa Carsuga you’ll find a lovely clean well-maintained property ideal for a peaceful holiday in Umbria. After a busy day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day.
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: Arezzo 29 km (18 mi), Cortona 45 km (28 mi), Gubbio 60 km (37 mi), Perugia 70 km (44 mi) and Assisi 75 km (47 mi).
Some other major tourist destinations you should consider visiting are: Florence 119 km (74 mi), Viareggio 203 km (126 mi), Forte Dei Marmi 213 km (132 mi), Rome 237 km (147 mi), Venice 332 km (206 mi) and Milan 398 km (247 mi).
Additional Information
Check-In Time: 15:00 - 21:00
Check-Out Time: 08:00 - 10:00
Pool Open: 27 June - 7 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) 124 km (77 mi), Pisa (psa) 187 km (116 mi), Bologna (blq) 195 km (121 mi), Roma Ciampino (cia) 246 km (153 mi) and Roma Fiumicino (fco) 259 km (161 mi).
Villa Bucatino
Villa Umbra
Amazing private villa rental with WIFI, A/C, private pool, sauna, TV, patio and panoramic view
- 15
- 7
- 4
Someone else is looking at this property right now!
Description
Villa Umbra is a nice stone building (600 sq m) with private pool, WiFi internet and air conditioning. The property can sleep up to 15 guests comfortably in seven bedrooms with four bathrooms. Villa Umbra is located 8 km (5 mi) from Città Di Castello, Italy and only 44 km (27 mi) from Arezzo in the tourist area "San Sepolcro And Surroundings".
What to Expect
When you arrive at Villa Umbra you’ll find a nice clean well-maintained property with views of the hills ideal for a relaxing holiday in Umbria. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of shopping. 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 15 people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
This beautiful farmhouse is divided internally into 3 non-communicating apartments: 1 (sleeps 5) on the ground floor and 2 (sleeps 4 and 6 people) upstairs. On the ground floor there is also a large room for the guests use, set up on 2 levels with large fireplace, tables and chairs, WC and 3 steps below: a big professional kitchen with oven, freezer, stove and dishwasher.
The area is renowned for its truffles and the owners organize (on request) wonderful truffle and game based dinners.
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: Arezzo 44 km (27 mi), Gubbio 56 km (35 mi), Cortona 59 km (37 mi), Perugia 60 km (37 mi) and Assisi 71 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 134 km (83 mi), Viareggio 221 km (137 mi), Forte Dei Marmi 228 km (141 mi), Rome 233 km (145 mi), Venice 345 km (214 mi) and Milan 407 km (253 mi).
Additional Information
Handicapped Accessible - If you or one of your guests needs wheelchair access, you’ll find at least one bedroom and bathroom that are accessible, as well as, most of the main rooms in the house.
Check-In Time: 14:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 24 April - 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) 141 km (88 mi), Pisa (psa) 202 km (125 mi), Bologna (blq) 206 km (128 mi), Roma Ciampino (cia) 246 km (153 mi) and Roma Fiumicino (fco) 258 km (160 mi).
Special Services
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a mouth-watering 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 extra costs.
Maid Service - If you'd like maid service during your trip that can be arranged by the owner. Ask for more details about the supplemental cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Villa Umbra. Ask for more details, including the additional cost and how to organize this service.
Villa Umbra
Book 10 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.
Monastery Guest House
Independent Holiday villa with hot tub, private pool, A/C, WIFI, TV, veranda, panoramic view
- 27
- 10
- 10
Someone else is looking at this property right now!
Description
Conveniently located 4 km (3 mi) from Città Di Castello, Italy in the tourist area "San Sepolcro And Surroundings" and only 34 km (21 mi) from Arezzo. Holiday home Monastery Guest House is a nice stone building (1000 sq m) that includes private pool, air conditioning and hot tub. The property can sleep up to 27 people comfortably in ten bedrooms with ten bathrooms.
The property is composed of 2 buildings: the main villa and the annex.Your Experience
When you arrive at Monastery Guest House you’ll find a beautiful clean well-maintained property with views of the hills perfect for a relaxing vacation in Umbria. After a busy 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. Outside you will also find a hot tub and barbecue grill. Dining with friends and family is a huge part of the Italian culture. Take advantage of the kitchen to prepare meals using local produce while on your holiday. The kitchen includes microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 27 people.
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: Arezzo 34 km (21 mi), Cortona 50 km (31 mi), Gubbio 55 km (34 mi), Perugia 58 km (36 mi) and Urbino 72 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 124 km (77 mi), Viareggio 208 km (129 mi), Forte Dei Marmi 218 km (135 mi), Rome 232 km (144 mi), Venice 336 km (209 mi) and Milan 396 km (246 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Monastery Guest House. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Handicapped Accessible - If you or one of your guests needs wheelchair access, you’ll find at least one bedroom and bathroom that are accessible, as well as, most of the main rooms in the house.
Check-In Time: 14:00 - 21:00
Check-Out Time: 08:00 - 11:00
Pool Open: 8 April - 10 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) 131 km (82 mi), Pisa (psa) 192 km (119 mi), Bologna (blq) 195 km (121 mi), Roma Ciampino (cia) 241 km (150 mi) and Roma Fiumicino (fco) 254 km (157 mi).
Additional Services
Baby Sitting - A babysitter can be arranged at Monastery Guest House. If you're traveling with kids and would like some alone time, talk to the owner directly about this option upon arrival.
Monastery Guest House
Montebello
Wonderful private holiday rental with private pool, WIFI, TV, patio, pets allowed and panoramic view
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- 5
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Someone else is looking at this property right now!
Description
Property Summary
The Montebello single-family house is a cozy and comfortable vacation rental situated among the characteristic hills of Umbria on the border with Tuscany, ideal for a relaxing stay. Surrounded by trees, fields, and vineyards in the hamlet of Citerna, it offers a well-kept garden with a lawn, a sunbathing area, a courtyard, and a seasonal swimming pool (12 x 6 m, depth 130 cm). The property also features internet Wi-Fi, a washing machine, and parking on the premises.
Outdoors
Enjoy the private, well-kept garden with a lawn area perfect for sunbathing, a courtyard, and a seasonal swimming pool measuring 12 x 6 meters with a depth of 130 cm, available from May 15 to September 25. Relax on the patio and take in the serene surroundings of trees, fields, and vineyards in Citerna.
Other Information
The property is conveniently located 10 km from the center of Anghiari, 25 km from Arezzo, and 40 km from Cortona. It is situated in a quiet, sunny position in the countryside, 60 km from the lake. Groups of teenagers are accepted upon request, but the owner does not accept youth groups.
Distances and Attractions
The Montebello house is just 1 km from a shop, 4 km from a supermarket, 1 km from a restaurant and café, and 12 km from the San Giustino railway station. A golf course is located 5 km away. Nearby attractions include the charming town of Città di Castello, just 14 km away, and the opportunity to explore the beautiful regions of Umbria and Tuscany, which are easily accessible from this ideal location. Montebello
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Description
Property Summary
Country House "La Valchiera" is a beautiful, recently renovated home nestled among trees, offering a tranquil retreat just 5 km from Sansepolcro, Italy. The property boasts a sunny, elevated position with stunning views, a terraced garden, natural pond, and a 10x5 meter swimming pool (100-130 cm deep) available seasonally from May 13th to October 6th. Enjoy the hot tub, patio, garden furniture, barbecue, and ample parking. Amenities include Internet WiFi, infrared sauna, relaxation room, spa area, washing machine, and tumble dryer.
Outdoors
Immerse yourself in the serene outdoor spaces of Country House "La Valchiera." The property spans an impressive 20 hectares, featuring a terraced garden, natural pond, and a beautiful swimming pool measuring 10 x 5 meters with a depth of 100-130 cm. The pool is available seasonally, from May 13th to October 6th. Unwind on the patio, where you'll find comfortable garden furniture and a barbecue for alfresco dining. Enjoy the convenience of having the pool maintained by the owner/gardener, allowing you to fully relax and soak up the sun.
Other Information
Country House "La Valchiera" offers a range of convenient amenities to enhance your vacation rental experience. Stay connected with internet access and enjoy the luxurious infrared sauna, relaxation room, and spa area. Laundry facilities, including a washing machine and tumble dryer, are available for your convenience. If you prefer not to cook, you can request a cook to prepare delicious meals for you. The nearest grocery store is just 4 km away, and a restaurant and bar are within 2 km, ensuring easy access to dining options.
Distances and Attractions
Country House "La Valchiera" is ideally situated near several attractions, making it the perfect base for exploring the area. For those who love horseback riding, a riding stable is conveniently located just 2 km away. The charming town of Anghiari, known for its rich history and picturesque streets, is only 15 km from the property. The vibrant city of Arezzo, with its impressive architecture and cultural offerings, is just 40 km away, offering plenty of opportunities for day trips and sightseeing. La Valchiera
Ville Rosadi Weddings
Beautiful private accommodation with private pool, A/C, hot tub, WIFI, TV, patio and panoramic view
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Description
If you are after a fairytale setting and wedding venue for your wedding in Tuscany then these incredible properties certainly fit the bill. Palazzo Rosadi and Torre del Cielo are two stunning villas in Monterchi that can be rented together to host special events and weddings, accommodating up to 22 people in 11 bedrooms (with 12 bathrooms, 11 of which are ensuite bathrooms) between the two properties. Located on a large and lovely estate that stretches across 25 hectares and is encircled by lush wooded surroundings, these romantic wedding villas are perched on a hillside with astounding views over the famous rolling hills of the Tuscan landscape. A perfectly picturesque and peaceful spot to escape daily life and concerns and to make beautiful memories as you start a life together, these pretty villas have all of the amenities and facilities that one could possibly need for an idyllic destination wedding in Tuscany.
Both typical stone-faced Tuscan villas with terracotta roofs, Palazzo Rosadi is the larger property with six bedrooms and seven bathrooms. Palazzo Rosadi also has a more grand and formal appearance and large interiors with high ceilings and spacious rooms. The decor is elegant with chic bedrooms, a large open-plan living and dining space, pretty little sitting rooms, a charming country kitchen, big bathrooms, and lots of wonderful details such as antique furniture, painted decorative patterns and designs on walls and ceilings, and more. Torre del Cielo, meanwhile, has five bedrooms and bathrooms and looks more like a romantic farmhouse nestled into a gorgeous garden that is alive with blooms. However, do not be deceived. It is still a relatively large villa with spacious interiors featuring exposed beam ceilings and stone walls, pretty bedrooms that really look like something from a storybook, a lovely big kitchen, and an open-plan dining and living room that boasts a massive fireplace. Both houses also boast air-conditioning in all of the bedrooms and WIFI throughout the properties. If you are thinking of getting married in Italy and you are looking for a wedding venue in Tuscany that can house both wedding receptions and your guests, then these romantic wedding villas make for the perfect setting.
The two properties are full of character but they are only made more appealing by the outdoor space of this estate with the woods; the three hectares of groomed gardens across three terraces; the endless outdoor dining areas and benches taking in pretty views of the Tuscan countryside for outdoor meals or escaping with a coffee and a good book for a while; and two swimming pools (one of which 12 x 6 mt; depth: 1,5 mt) with sun-loungers, a heated Jacuzzi (avaliable on request), and an old stone barn that has been made into a large shower and changing room with bathroom facilities. This wonderful exterior space of the estate is ideal for an outdoor wedding and means that incredible wedding meals can be arranged at tables set up on those terraces taking in sweeping views across the rolling hills of the Tuscan landscape, wedding ceremonies can take place in the pretty Italian garden with flowers all around, and your guests have plenty to do and keep themselves occupied with around the special day, allowing everyone to make incredible memories. For your wedding photography, too, there are endless stunning backdrops to perfectly capture your magical and romantic wedding in this fairytale setting.
So, if you having been dreaming of a destination wedding in Tuscany and having your special day in the most magical of settings then be sure to get in touch about these truly stunning wedding villas in Tuscany. Make your dream wedding in Italy a reality:
Palazzo Rosadi - max capacity: 12 bedrooms : 6 bathrooms : 7
Torre del Cielo - max capacity: 10 bedrooms : 5 bathrooms : 5
Extra services
The owners of Palazzo Rosadi can organise all sorts of other services including preparing breakfast and dinner, offering a cooking class with a chef, maid services, babysitting, car/van hire, an English-speaking guide, a wine tour with English-speaking driver and van (all day, 2 wine tastings plus lunch in a typical restaurant), transfer to and from the airport, and hot air ballooning (an exceptionally romantic wedding experience) to further enhance your trip and your wedding in Italy.
Palazzo Rosadi and Torre del Cielo are about 70 meters apart.
The maximum number of guests admitted for the reception is 22 (internally) or up to totally 55 (if the party is held externally).
For any more detailed info about each accommodation, you can check the property #EAS 153756 and #EAS 153757 Palazzo Rosadi And Torre Del Cielo - Weddings And
