Luxury Villas with Pool in Simignano, Italy
Results 81 - 97 of 97
Villa Montisi
Unique private holiday home with private pool, A/C, WIFI, TV and patio
0% Interest Installments-
6
-
3
-
3
Description
Property Summary
The modern and beautiful two-story Villa Montisi, built in 2020, is surrounded by trees and fields in Montisi, 15 km from Montalcino. It offers a private garden with flowers, trees, and a seasonal swimming pool (4 x 12 m, depth 120 - 150 cm, available from May 1 to September 30) with an internal staircase. Additionally, it features amenities such as air conditioning, a washing machine, a tumble dryer, and parking on the premises. The villa is an ideal vacation rental for those seeking a peaceful retreat in the Tuscan countryside.
Outdoors
The villa boasts a beautiful private garden with flowers and trees, providing a serene outdoor space for relaxation. The highlight is the seasonal swimming pool (4 x 12 m, depth 120 - 150 cm), available from May 1 to September 30, complete with an internal staircase for easy access. Outdoor amenities include a shower, garden furniture, and a barbecue area, ensuring a comfortable and enjoyable outdoor experience. The pool is maintained by the owner or gardener.
Other Information
Conveniently located just 500 m from the center of Montisi, the villa offers easy access to nearby amenities. A shop and grocery store are within 500 m, while a supermarket is 10 km away. Restaurants are also available within a 5-minute walk, and the bus stop "Montisi" is 500 m from the property. For those traveling with young children, baby equipment is included.
Distances and Attractions
The villa is situated in a desirable location, with several nearby attractions easily accessible. Montalcino, renowned for its wine production, is just 23 km away, while the charming towns of Pienza and Montapulciano are within 30 km and 25 km, respectively. The historic city of Siena is approximately 50 km from the property, offering rich cultural experiences and architectural marvels. Trequanda, Italy, is also in close proximity, adding to the region's appeal for travelers seeking an authentic Tuscan experience. Villa Montisi
Villa Marina
Beautiful private vacation home with WIFI, private pool, A/C, TV and pets allowed
-15% Special Offer-
10
-
5
-
5
-
300 m2
Description
Up to 10 guests, 5 beds / 5 baths: this old tuscan farmhouse is located in the heart of the Arno Valley, between Firenze/Florence, Arezzo, Chianti and Siena.
Very centrally located to explore the region, what make this area unique is its authenticity and opportunity to discover Tuscany off the beaten path, thank to our connections: ASK for our concierge service or service list!
Remote but yet very close to nearby towns (about 6 km away from shops, supermarket, train station and highway). You will get to the property by a short private dirt road, driving through vineyards and beautiful mountain and hills views.
Fully immersed in nature and countryside, this is THE getaway to rejoice with nature, silence and breathe Tuscany in every way. The villa is very big, with very spacious rooms and surrounded by greenery and birds singing.
The indoor is typical tuscan, with every comfort such as wifi, wood oven, television with streaming mode and a private Home Cinema!
Wide property with fields and woods for you to take lovely walks around the property, do your yoga sessions or to simply sit under the shade of the pergola. The villa is open also for private events, small weddings, ceremonies or any project we could help realize!
The private pool is 12*5 mt, open from May 1st until Sept 30, with decks, chairs and lots of reading corners!
PETS LIVE ON PROPERTY, housekeeper lives nearby. Villa Marina
Town House Garden
Comfortable home with A/C, private pool and TV, near Montepulciano
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9
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5
-
4
-
350 m2
Description
Town House Garden is located , Italy and only 21 km (13 mi) from Montepulciano in the tourist area "Orcia Valley". Town House Garden is a beautiful stone building (350 sq m) with private pool and air conditioning. The property can accommodate up to nine people comfortably in five bedrooms with four bathrooms.
The Experience
Upon arrival you’ll find a nice clean well-maintained property perfect for a peaceful holiday in Tuscany. Regardless of how you spend your days - shopping, sightseeing, 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. 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 toaster and refrigerator, as well as, plenty of tableware and cutlery for up to nine people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the perfect setting to enjoy food, family and the nice Tuscan weather.
Visit the Area
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: Montepulciano 21 km (13 mi), Montalcino 27 km (17 mi), Cortona 43 km (27 mi), Arezzo 56 km (35 mi) and Siena 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 128 km (79 mi), Viareggio 214 km (133 mi), Forte Dei Marmi 221 km (138 mi), Rome 209 km (130 mi), Milan 414 km (257 mi) and Naples 400 km (249 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 1 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) 133 km (83 mi), Pisa (psa) 195 km (121 mi), Bologna (blq) 220 km (136 mi), Roma Ciampino (cia) 226 km (140 mi) and Roma Fiumicino (fco) 231 km (144 mi).
Town House Garden
Villa Guardistallo
Wonderful independent property with private pool, WIFI, A/C, TV, terrace and panoramic view
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21
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8
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10
Description
Villa Guardistallo is a nice holiday home with private pool, WiFi internet and air conditioning. The property can accommodate up to 21 guests comfortably in eight bedrooms with ten bathrooms. Villa Guardistallo is located 10 km (6 mi) from Guardistallo, Italy and only 59 km (36 mi) from San Gimignano in the tourist area "Tuscan Coast".
Your Experience
After arriving at Villa Guardistallo you’ll find a nice clean well-maintained property with views of the hills perfect for a peaceful vacation in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of shopping.
Places 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: San Gimignano 59 km (36 mi), Pisa 78 km (48 mi), Siena 81 km (50 mi), Viareggio 96 km (60 mi) and Greve In Chianti 98 km (61 mi).
Some other major tourist destinations you should consider visiting are: Florence 128 km (79 mi), Viareggio 96 km (60 mi), Forte Dei Marmi 108 km (67 mi), Rome 303 km (188 mi), Venice 373 km (232 mi) and Milan 349 km (217 mi).
Additional Information
Pool Open: 15 April - 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): Pisa (psa) 72 km (45 mi), Firenze Peretola (flr) 130 km (80 mi), Bologna (blq) 222 km (138 mi), Genova (goa) 238 km (148 mi) and Roma Fiumicino (fco) 286 km (177 mi).
Villa Guardistallo
Castello di Quarate
Independent House with WIFI, A/C, private pool, TV, patio, panoramic view, close to Greve In Chianti
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14
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7
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7
-
900 m2
Description
Conveniently located 3 km (2 mi) from San Polo In Chianti, Italy in the tourist area "Florence And Surroundings" and only 15 km (9 mi) from Greve In Chianti. Vacation rental Castello Di Quarate is a nice property (900 sq m) that includes air conditioning, WiFi internet and private pool. The property can accommodate up to 14 people comfortably in seven bedrooms with seven bathrooms.
The Experience
When you arrive you’ll find a nice clean well-maintained property with views of the hills ideal for a relaxing holiday in Tuscany. After a hectic day of visiting museums, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day.
Places 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 15 km (9 mi), Florence 19 km (11 mi), San Gimignano 58 km (36 mi), Arezzo 69 km (43 mi) and Siena 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 19 km (11 mi), Viareggio 119 km (74 mi), Forte Dei Marmi 127 km (79 mi), Rome 273 km (170 mi), Venice 272 km (169 mi) and Milan 320 km (199 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.
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) 38 km (24 mi), Pisa (psa) 100 km (62 mi), Bologna (blq) 125 km (77 mi), Genova (goa) 258 km (160 mi) and Venezia (vce) 278 km (173 mi).
Additional Services
Maid Service - If you'd like maid service during your trip that can be arranged by the owner. Inquire for more details about the additional cost.
Baby Sitting - A babysitter can be arranged at Castello Di Quarate. If you're traveling with kids and would like some alone time, talk to the owner directly about this option upon arrival.
Castello Di Tizzano
Villa Ombrone
Independent House with private pool, WIFI, A/C, sauna, TV, patio, pets allowed, panoramic view
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6
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3
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4
-
160 m2
Description
Conveniently located 12 km (8 mi) from Campagnatico, Italy in the tourist area "Grosseto - Maremma" and only 53 km (33 mi) from Montalcino. Villa Ombrone is a nice vacation rental (160 sq m) with WiFi internet, private pool and air conditioning. The property can sleep up to six guests comfortably in three bedrooms with four bathrooms.
The Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. 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. Also available outdoors are a barbecue grill, playground and patio.
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: Montalcino 53 km (33 mi), Siena 72 km (45 mi), Montepulciano 89 km (55 mi), San Gimignano 110 km (68 mi) and Greve In Chianti 112 km (69 mi).
Some other major tourist destinations you should consider visiting are: Florence 140 km (87 mi), Viareggio 188 km (117 mi), Forte Dei Marmi 200 km (124 mi), Rome 203 km (126 mi), Venice 386 km (240 mi) and Milan 446 km (277 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Ombrone. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 17:00 - 23:00
Check-Out Time: 06:00 - 10:00
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) 148 km (92 mi), Pisa (psa) 165 km (102 mi), Roma Fiumicino (fco) 186 km (115 mi), Roma Ciampino (cia) 208 km (129 mi) and Bologna (blq) 239 km (148 mi).
Villa Ombrone
Il Sogno Toscano
Independent Holiday villa with private pool, WIFI, A/C, TV, patio, pets allowed, panoramic view
0% Interest Installments-
6
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3
-
2
Description
Property Summary
Nestled in the heart of the Tuscan countryside, "Il Sogno Toscano" is a charming rustico cottage that captures the timeless spirit of rural Italy. This typical Tuscan country house spans 2 storeys and was fully renovated in 2025, offering a seamless blend of traditional character and contemporary comfort. Situated just 3 km from the centre of Casale Marittimo, this exceptional holiday rental enjoys an absolutely fantastic location with beautiful panoramic views over the rolling Tuscan landscape, while remaining conveniently close to the coast. The property sits within a generous 1 ha fenced estate, providing complete privacy and a sense of seclusion that is truly rare. A beautiful garden invites you to unwind and reconnect with nature, while the private swimming pool measuring 8 x 4 m offers a refreshing retreat during the warmer months. Wireless internet connection is available throughout the property, ensuring you remain connected whenever needed. Parking is conveniently provided directly at the house, accessible via a 100 m long steep motor access road leading to the grounds.
Outdoors
The outdoor spaces of "Il Sogno Toscano" are thoughtfully designed to make the most of the stunning natural surroundings. The private swimming pool, measuring 8 x 4 m with a depth ranging from 135 to 140 cm, is available seasonally from 1 May to 31 October and is maintained by the owner's gardener, ensuring it remains in pristine condition throughout your stay. An outdoor shower is conveniently located nearby for rinsing off after a swim. The expansive fenced grounds of 1 ha encompass a beautifully kept garden where you can relax in complete tranquillity, surrounded by the gentle Tuscan landscape. A pergola and a patio provide shaded areas ideal for outdoor dining and leisurely afternoons, while a terrace offers additional space to enjoy the sweeping countryside views. A barbecue area is available for alfresco meals, and a basketball court adds a recreational dimension to the outdoor offering, making the property equally suited to families and groups seeking both relaxation and activity.
Other Information
Linen changes are available during your stay at a supplementary charge. Towel changes are likewise offered at an additional cost. Please note that pool maintenance is carried out regularly by the owner or gardener, ensuring the swimming facilities are always well kept. The property is accessed via a 100 m long steep motor access road leading to the grounds, which guests should bear in mind when planning their arrival.
Distances and Attractions
"Il Sogno Toscano" benefits from a privileged position that places a wealth of destinations and services within easy reach. The centre of Casale Marittimo is just 3 km away, while the centre of Bibbona can be reached in approximately 4.4 km. The nearest grocery store and supermarket are both located 3 km from the property, and a shop is available 11 km away. A bus stop is situated just 1.6 km from the cottage, offering a convenient public transport connection. The sea and beach are both 13 km away, making the property an excellent base for coastal excursions, while a marina is located 15 km from the house. Golf enthusiasts will appreciate the proximity of a 9-hole golf course just 8.5 km away. Among the most notable nearby attractions, the celebrated village of Bolgheri, renowned for its wine production and scenic cypress-lined avenue, is only 10 km away. The historic hilltop city of Volterra lies 30 km from the property, offering remarkable Etruscan heritage and medieval architecture. Pisa, home to its iconic leaning tower, is reachable within 75 km, and the magnificent city of Florence, with its unparalleled artistic and cultural treasures, is situated 110 km away. Il Sogno Toscano
Villa Peccioli
Fabulous independent holiday home with WIFI, private pool, A/C, TV and veranda
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11
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4
-
5
-
300 m2
Description
Holiday rental Villa Peccioli is a beautiful stone building (300 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to 11 people comfortably in four bedrooms with five bathrooms. Villa Peccioli is located 11 km (7 mi) from Peccioli, Italy and only 46 km (28 mi) from San Gimignano.
What to Expect
After arriving you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills ideal for a splendid holiday in Tuscany. Regardless of how you spend your days - shopping, sightseeing, visiting museums 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.
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: San Gimignano 46 km (28 mi), Pisa 51 km (32 mi), Viareggio 80 km (50 mi), Florence 81 km (50 mi) and Lucca 84 km (52 mi).
Some other major tourist destinations you should consider visiting are: Florence 81 km (50 mi), Viareggio 80 km (50 mi), Forte Dei Marmi 92 km (57 mi), Rome 362 km (225 mi), Venice 322 km (200 mi) and Milan 338 km (210 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 March - 15 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): Pisa (psa) 53 km (33 mi), Firenze Peretola (flr) 82 km (51 mi), Bologna (blq) 175 km (108 mi), Genova (goa) 228 km (142 mi) and Roma Fiumicino (fco) 325 km (202 mi).
Villa Francesca
La Fonte
Amazing independent holiday villa with A/C, private pool, WIFI, TV and patio
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8
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4
-
2
-
180 m2
Description
La Fonte is located in Palaia, Italy and only 42 km (26 mi) from San Gimignano. Holiday home La Fonte is a beautiful stone building (180 sq m) that includes air conditioning, WiFi internet and private pool. The property can sleep up to eight guests comfortably in four bedrooms with two bathrooms.
What to Expect
This pretty property is located in a very quiet position within walking distance of the 12th century village of Palaia, and has beautiful views over the surrounding olive groves, vineyards and medieval villages. The outside living spaces and the fenced garden are particularly well maintained and make the property ideal for families with children. On one side of the house there is a covered loggia, furnished for outdoor dining. There is a second outdoor dining area with built in barbecue/oven allowing guests to dine in the Tuscan sunshine.
After arriving you’ll find a beautiful clean well-maintained property with views of the hills ideal for a relaxing 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. Outside you will also find 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, microwave, toaster 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 lovely 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: San Gimignano 42 km (26 mi), Pisa 43 km (26 mi), Lucca 58 km (36 mi), Florence 63 km (39 mi) and Viareggio 72 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 63 km (39 mi), Viareggio 72 km (44 mi), Forte Dei Marmi 83 km (52 mi), Rome 344 km (214 mi), Venice 308 km (191 mi) and Milan 327 km (203 mi).
Additional Information
There is a billiard table in the living room.
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): Pisa (psa) 44 km (27 mi), Firenze Peretola (flr) 66 km (41 mi), Bologna (blq) 160 km (99 mi), Genova (goa) 217 km (135 mi) and Treviso (tsf) 313 km (194 mi).
Special 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.
Cleaning service is included 9 hours a week. La Fonte
Villa Asciolo
Amazing independent property with WIFI, A/C, private pool and terrace
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22
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10
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11
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500 m2
Description
Villa Asciolo is a lovely holiday rental (500 sq m) with air conditioning, WiFi internet and private pool. The property can accommodate up to 22 guests comfortably in ten bedrooms with 11 bathrooms. Villa Asciolo is located 5 km (3 mi) from Palaia, Italy and only 43 km (27 mi) from Pisa.
The road to the property is asphalted, but the last section of the track is unpaved.
The Experience
When you arrive you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills perfect for a relaxing holiday in Tuscany. 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. There is a kitchen including coffee machine, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 22 people. If you prefer to dine 'al fresco', there is a fully furnished terrace 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: Pisa 43 km (27 mi), San Gimignano 44 km (27 mi), Lucca 55 km (34 mi), Florence 60 km (37 mi) and Greve In Chianti 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 60 km (37 mi), Viareggio 72 km (45 mi), Forte Dei Marmi 84 km (52 mi), Rome 341 km (212 mi), Venice 305 km (189 mi) and Milan 328 km (203 mi).
Additional Information
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): Pisa (psa) 45 km (28 mi), Firenze Peretola (flr) 63 km (39 mi), Bologna (blq) 154 km (95 mi), Genova (goa) 215 km (133 mi) and Venezia (vce) 307 km (191 mi).
Villa Poggio Asciolo
Centolivi 14
Wonderful independent villa rental with WIFI, private pool, A/C, TV, patio and panoramic view
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14
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7
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6
-
400 m2
Description
Centolivi 14 is a nice stone building (400 sq m) with air conditioning, WiFi internet and private pool. The property can sleep up to 14 guests comfortably in seven bedrooms with six bathrooms. Conveniently located 5 km (3 mi) from Palaia, Italy and only 36 km (22 mi) from Pisa.
What to Expect
The property consists of a main house and a guest house. The main entrance to the property leads through a shady courtyard and covered loggia to a large terrace enjoying wonderful views over the landscape. Part of the large garden is an olive grove and the swimming pool (12x6m) has been placed in a spectacular position. There is also an original bread oven which can be used for pizzas and barbecues too.
After arriving you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing holiday in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping 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. Also available outside are 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 vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 14 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the nice Tuscan weather.
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: Pisa 36 km (22 mi), San Gimignano 42 km (26 mi), Lucca 43 km (27 mi), Florence 61 km (38 mi) and Viareggio 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 61 km (38 mi), Viareggio 65 km (40 mi), Forte Dei Marmi 76 km (47 mi), Rome 342 km (212 mi), Venice 302 km (187 mi) and Milan 320 km (199 mi).
Additional Information
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): Pisa (psa) 37 km (23 mi), Firenze Peretola (flr) 62 km (38 mi), Bologna (blq) 154 km (96 mi), Genova (goa) 207 km (129 mi) and Venezia (vce) 308 km (191 mi).
Additional Services
Maid Service - If you'd like maid service during your visit that can be arranged by the owner. Ask for more details about the extra cost.
Cleaning service is included 3 hours a day, 3 days a week. Centolivi 14
Villa di Seripa
Fabulous private holiday home with A/C, private pool, WIFI, TV and patio
0% Interest Installments-
20
-
9
-
9
-
500 m2
Description
Villa Di Seripa is a beautiful holiday rental (500 sq m) with air conditioning, WiFi internet and private pool. The property can sleep up to 20 people comfortably in nine bedrooms with nine bathrooms. Conveniently located 6 km (4 mi) from Sassetta, Italy in the tourist area "Grosseto - Maremma" and only 87 km (54 mi) from Pisa. There is a golf course nearby if you'd like to get in a round or two while on holiday.
The owners live on site, in a completely separate villa at about 50 m distance from the rental.
Your Experience
When you arrive you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property ideal for a splendid vacation 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. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the kitchen to prepare meals using local produce while on your vacation. The kitchen includes microwave and refrigerator, as well as, plenty of tableware and cutlery for up to 20 people.
Visit the Area
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: Pisa 87 km (54 mi), San Gimignano 91 km (57 mi), Viareggio 113 km (70 mi), Lucca 117 km (73 mi) and Montalcino 122 km (76 mi).
Some other major tourist destinations you should consider visiting are: Florence 145 km (90 mi), Viareggio 113 km (70 mi), Forte Dei Marmi 125 km (78 mi), Rome 262 km (163 mi), Venice 391 km (243 mi) and Milan 367 km (228 mi).
Additional Information
Check-In Time: 15:00 - 22:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 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): Pisa (psa) 90 km (56 mi), Firenze Peretola (flr) 149 km (92 mi), Bologna (blq) 239 km (149 mi), Roma Fiumicino (fco) 245 km (152 mi) and Genova (goa) 259 km (161 mi).
More Services
Cooking Lessons - Learn from a local chef the techniques needed to master Tuscan cuisine. The owner can organize 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 learning the secrets needed to prepare mouth-watering Tuscan meals when you return home. For more details and the extra cost, please contact us.
Maid Service - If you'd like maid service during your trip that can be arranged by the owner. Inquire for more details about the additional cost.
Tenuta Di Seripa
Il Canto del Maggio
Great accommodation with pool, A/C, WIFI, TV, patio, pets allowed and panoramic view
-15% Special Offer-
6
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14
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6
-
6
| Accommodation | Sleeps | Bedrooms | Bathrooms | Price |
|---|---|---|---|---|
| La Castellana | 2 | 1 | 1 | € 68 /Night |
| Canto al Sole | 2 | 1 | 1 | € 68 /Night |
| Bellina | 2 | 1 | 1 | € 68 /Night |
| All 3 Accommodations | 6 | 3 | 3 |
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
Podere Palazzo
Beautiful independent holiday home with A/C, WIFI, private pool and panoramic view, near Montalcino
0% Interest Installments-
8
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3
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3
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200 m2
Description
Vacation rental Podere Palazzo is a nice property (200 sq m) that includes private pool, WiFi internet and air conditioning. The property can accommodate up to eight guests comfortably in three bedrooms with three bathrooms. Conveniently located 3 km (2 mi) from Castiglione D'orcia, Italy in the tourist area "Orcia Valley" and only 24 km (15 mi) from Montalcino.
The Ground Floor can't be rented and it is closed, as the owners live there occasionally.
They may use the pool too, when they are at the villa.
The Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property ideal for a relaxing holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of visiting museums.
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 24 km (15 mi), Montepulciano 31 km (19 mi), Siena 58 km (36 mi), Cortona 70 km (43 mi) and Arezzo 92 km (57 mi).
Some other major tourist destinations you should consider visiting are: Florence 125 km (78 mi), Viareggio 220 km (137 mi), Forte Dei Marmi 227 km (141 mi), Rome 197 km (123 mi), Venice 376 km (234 mi) and Milan 419 km (260 mi).
Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 07:00 - 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) 140 km (87 mi), Pisa (psa) 185 km (115 mi), Roma Ciampino (cia) 206 km (128 mi), Roma Fiumicino (fco) 219 km (136 mi) and Bologna (blq) 221 km (137 mi).
Birthdays and parties are generally not accepted, especially for groups of young people under the age of 30.
Podere Palazzo
Villa Gaeta
Private Holiday villa with private pool, WIFI, A/C, TV, panoramic view, close to Montepulciano
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10
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5
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5
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240 m2
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
Villa Botinaccio
Stunning independent vacation home with private pool, A/C, WIFI, TV, patio and panoramic view
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11
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6
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6
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500 m2
Description
Conveniently located 3 km (2 mi) from Bobolino, Italy in the tourist area "Florence And Surroundings" and only 27 km (17 mi) from Florence. Vacation rental Villa Botinaccio is a nice stone building (500 sq m) that includes WiFi internet, private pool and air conditioning. The property can sleep up to 11 guests comfortably in six bedrooms with six bathrooms.
The Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills ideal 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 unwind at the end the day. Outdoors you will also find a patio and barbecue grill. 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, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 11 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: Florence 27 km (17 mi), San Gimignano 36 km (22 mi), Greve In Chianti 39 km (24 mi), Pisa 60 km (37 mi) and Lucca 65 km (40 mi).
If you'd like to visit the beautiful Tuscan coast, it's just a short driving distance to the sea from the property, only 70 m (211 ft).
Some other major tourist destinations you should consider visiting are: Florence 27 km (17 mi), Viareggio 89 km (55 mi), Forte Dei Marmi 101 km (63 mi), Rome 308 km (192 mi), Milan 316 km (196 mi) and Naples 499 km (310 mi).
Additional Information
Check-In Time: 15:00 - 19:00
Check-Out Time: 09:00 - 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) 29 km (18 mi), Pisa (psa) 62 km (38 mi), Bologna (blq) 121 km (75 mi), Genova (goa) 232 km (144 mi) and Venezia (vce) 274 km (170 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can organize 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 required to prepare sumptuous Tuscan meals when you return home. For more details and the extra 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 arrange 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 additional costs.
Maid Service - If you'd like maid service during your stay that can be arranged by the owner. Ask for more details about the supplemental cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your vacation hassle-free after a long trip. Ask for more details, including the extra cost and how to schedule this service.
Baby Sitting - A babysitter can be scheduled at Villa Botinaccio. If you're traveling with kids and would like some alone time, talk to the owner directly about this option when you arrive.
The Cooking Lesson includes shopping, preparing the dishes together with the guests, service and tidying up final, a bottle of Chianti for tasting for every 4 participants. Included in the lunch or dinner will also be served a traditional Tuscan side dish, such as Panzanella or Pappa al Pomodoro or a rich salad.
The menus adapt to the season and the dietary needs of the guests and are constructed so that guests can work at their best.
Lessons usually start around 10.00 or 17.00 and last about two hours plus time for lunch or dinner. The times are however flexible to be agreed with the guests. Villa Colle Di Sotto
Podere Boscherini
Fabulous private vacation home with WIFI, private pool, A/C, patio, pets allowed and panoramic view
Special Offer 0% Interest Installments-
6
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3
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3
Description
Property Summary
Set in Riparbella, Italy, Podere Boscherini is a charming "rustico" cottage comprising a main house and outbuilding. This vacation rental features a seasonal swimming pool (12 x 6 m) available from April 1st to October 31st, a well-maintained yard with lawn areas, complimentary Internet WiFi, and convenient on-site parking facilities. The property occupies a private, elevated position, offering seclusion and tranquility.
Outdoors
The exterior spaces include a meticulously maintained garden with sunbathing areas, an outdoor shower, and complete garden furniture. A barbecue facility is available for al fresco dining. The swimming pool, featuring an internal staircase and depths ranging from 120 to 200 cm, is surrounded by natural landscapes of trees and meadows.
Other Information
The property provides additional services including linen and towel changes for a supplementary charge. The owner maintains a policy of not accepting youth groups. The accommodation is positioned 3 kilometers from Riparbella's center, ensuring privacy while maintaining accessibility to local amenities.
Distances and Attractions
The property is conveniently located with various amenities nearby: shops and grocery stores at 4 km, a restaurant and bus stop "La Melatina" at 2 km, and the beach at 14 km. Notable attractions include the Calidario thermal baths (45 km), Marina (16 km), and a 9-hole golf course (20 km). Cultural destinations within reach include Bolgheri (25 km), Volterra (30 km), Pisa (60 km), and Florence (100 km). Podere Boscherini