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Featured Villas in Castiglion Fiorentino

Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Outdoor pool

Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi

10.0 out of 10, Exceptional, (45)
"Luigi went above and beyond in providing suggestions of restaurants and things to do in the area. He was also helpful when we were have trouble calling our car rental….always willing to help out and answer questions. The home is very clean and has the old Italian rustic charm. The beds were comfortable. There is no AC but fans are provided for every room. There were beautiful sunsets every night by the pool. The views of the rolling Tuscan hills were spectacular. The color and intensity of the...
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
Outdoor pool

Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!

9.8 out of 10, Exceptional, (29)
"We are traveling with 6 persons through Italy. This villa was a wonderful change of pace to the crowded streets of the cities. Beauty, clean, and well stocked. A little off the grid but worth the train rides and car rental. "
Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Pool

Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the

Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (78)
"We absolutely loved our stay at this villa! It was just wonderful, and Luigi was a fantastic host! The views from every part of the villa are amazing! It was so fun to see all of the sheep each morning and watch the sunset in the evenings. We were fortunate enough to be in town for the olive festival in Montisi, the quaint little village just a few miles away. We had a blast! The recommended chef who cooked for us at the villa, Giancarlo from the Tuscan Chef, was incredible! What a fantastic...
Villa in Montalcino, exclusive for you, stunning view!!!
Heritage Tuscan Farmhouse with private swimming pool
Pool

Heritage Tuscan Farmhouse with private swimming pool

10.0 out of 10, Exceptional, (44)
"We had a very happy stay at this house in the country with our two friends. It is ideally located within an hour’s drive of interesting sites and historic towns. The place and its surroundings allowed us a restful and pleasant respite from our busier daytrips. The house was comfortable, beds were very good and the garden provided a peaceful setting with a choice of sitting and lounging areas. Louise was lovely, an excellent hostess who responded quickly to our questions and needs. "
Heritage Tuscan Farmhouse with private swimming pool
Charming Villa with private pool <br>Villaventotto
Pool

Charming Villa with private pool <br>Villaventotto

9.8 out of 10, Exceptional, (16)
"We had a great time. We stayed for two days"
The price is AU$827
includes taxes & fees
3 Dec - 4 Dec
Charming Villa with private pool <br>Villaventotto
Villa Costa Piccola with private pool "amazing holiday in green heart of Italy"
Point of interest

Villa Costa Piccola with private pool "amazing holiday in green heart of Italy"

9.8 out of 10, Exceptional, (26)
"What an awesome property! Our host was not only knowledgeable of area but was an excellent chef! The villa exceeded all our expectations. It is strategically located to visit towns and historical sites! A must stay!"
Villa Costa Piccola with private pool "amazing holiday in green heart of Italy"
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Outdoor pool, pool loungers

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

10.0 out of 10, Exceptional, (1)
"Beautiful villa in fantastic location . Easy to get to many places and attractions. Well equipped and very comfy beds. Lovely helpful owner. Would love to return."
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Charming Tuscany Villa with magical Garden, shared pool, Chianti Area
Outdoor dining

Charming Tuscany Villa with magical Garden, shared pool, Chianti Area

9.4 out of 10, Exceptional, (51)
"We had a lovely stay a few weeks ago in this charming old stone house with gorgeous gardens surrounded by vineyards and olive groves. A great base as we explored Tuscany for 4 days."
Charming Tuscany Villa with magical Garden, shared pool, Chianti Area
Perfect villa in Umbria stunning private infinity pool, superb views, sleeps 12
Exterior

Perfect villa in Umbria stunning private infinity pool, superb views, sleeps 12

10.0 out of 10, Exceptional, (14)
"An exceptional house and infinity pool in the hills close to Montone. The children spent many hours in the pool and we all had a barbecue supper on the patio in the evening. The accommodation was wonderful and the kitchen allowed us all to help with cooking. Our master bedroom was very comfortable and had netting on the windows to stop the insects. Amazing property."
Perfect villa in Umbria stunning private infinity pool, superb views, sleeps 12
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
Dining

Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren

10.0 out of 10, Exceptional, (1)
"Bellissimo casolare ben tenuto con magnifico giardino e grande piscina. La padrona di casa gentilissima e molto discreta. Abbiamo soggiornato in agosto con amici e ci siamo trovati benissimo. Assolutamente consigliato!"
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
ancient villa with pool and park in total privacy
Outdoor pool

ancient villa with pool and park in total privacy

9.6 out of 10, Exceptional, (21)
"Had a great stay at Villa Flaminio. The pool is fantastic and set in shady grounds. Lovely bbq. Supermarket close by. Also a great restaurant, Ostetia dell accademia, in walking distance. Nice, friendly manager who fixed an issue with the cooker within an hour."
ancient villa with pool and park in total privacy
Holiday Home La Limonaia - Lovely restored baronial guesthouse
Property grounds

Holiday Home La Limonaia - Lovely restored baronial guesthouse

10.0 out of 10, Exceptional, (35)
"The loveliest place we have ever stayed through VRBO. La Limonia exceeds all expectations. Wander the property, explore the many gardens. Relax. Enjoy. Many thanks to Margareth and Arthur who were exceptional hosts, kind, friendly and helpful. Polly, Don, Chuck and Mary Jo"
Holiday Home La Limonaia - Lovely restored baronial guesthouse
2-bedroom house immersed in the Tuscan countryside, less than 2 km from the village of Castelluccio
Pool

2-bedroom house immersed in the Tuscan countryside, less than 2 km from the village of Castelluccio

2-bedroom house immersed in the Tuscan countryside, less than 2 km from the village of Castelluccio
Beautiful 4 bed 4 bath private villa with breathtaking views and infinity pool
Outdoor pool

Beautiful 4 bed 4 bath private villa with breathtaking views and infinity pool

10.0 out of 10, Exceptional, (7)
"This is our second visit to Annie's beautiful farmhouse and we hope to visit again next year. It's an incredibly special place - perfectly peaceful, thoughtfully and generously furnished and child friendly. Selfishly we hope the house doesn't become too popular! Thanks again Annie for letting us stay."
Beautiful 4 bed 4 bath private villa with breathtaking views and infinity pool
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Exterior

Magnifica villa in toscana, 7 posti letto, con vista incredibile!!

10.0 out of 10, Exceptional, (2)
"Such a quaint home, clean, quiet and beautiful. Close to the center of the very small town of Montepulciano. The host is very sweet and even cooked a cake to welcome us to their home. The view of the valley from the home is simply breathtaking."
The price is AU$867
includes taxes & fees
3 Dec - 4 Dec
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Outdoor dining

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

8.8 out of 10, Excellent, (3)
"This house is very nice. It is centrally located outside Siena and good location to explore all over Tuscany. It is off the beaten path so you’ll definitely need a rental car. Even just to get there. It is remote. Which is a plus but also has some drawbacks. We went in March so pool was closed. Too cold to swim. House is several levels. Kitchen and dining room are downstairs. We cooked several simple meals after going into town to grab groceries. Nearby town is nice. Not a lot of restaurant...
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Dimora di Castroncello
Pool

Dimora di Castroncello

10.0 out of 10, Exceptional, (3)
"Wir verbrachten super Ferien in diesem tollem Haus, auch unsere Hunde hatten Spass. Die Eigentümer, Elisa und Alessandro, sind fantastisch, herzlich und sehr hilfsbereit. Sie haben uns am ersten Abend mit einem sehr feinen Nachtessen verwöhnt. Das Dorf Castiglion Fiorentino bietet alles was man braucht. Nochmals Danke für alles."
Dimora di Castroncello
Vrbo Property
Interior

Vrbo Property

10.0 out of 10, Exceptional, (3)
"A wonderful Umbrian property with spectacular views over the lake. Paola was really helpful and we had a couple of great trips to recommended restaurants. Great relaxing view"
Vrbo Property
Private villa with 5 bedrooms with 5 bathrooms. Private garden, pool & Jacuzzi!
Outdoor dining

Private villa with 5 bedrooms with 5 bathrooms. Private garden, pool & Jacuzzi!

9.6 out of 10, Exceptional, (9)
"The villa was truly magical. It was everything we wanted and more. There was plenty of space for my family of six adults and four children. The location was excellent! We were able to visit the nearby towns of Cortona, Lucignano, Sinalunga and Montepulciano. We also drove to Florence which is about an hour away. Paolo was extremely helpful from reservations through check out. He also arranged to get us an amazing chef for one of our dinners. It was a vacation we will be talking about for years...
Private villa with 5 bedrooms with 5 bathrooms. Private garden, pool & Jacuzzi!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Castiglion Fiorentino

Farmhouse in the hills with panoramic view and swimming pool
Pool

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (66)
"We stayed for 10 days recently and had a great time, the house was easy to find and the host answered our queries straight away, he also visited the property every other day to water the plants and check that everything was ok. We had a problem with the dishwasher one day and an electrician turned up within 30 minutes. The photos of the house are true to life and the views from the shaded terrace are amazing. The pool was used almost every day and was cleaned regularly usually early before we...
Farmhouse in the hills with panoramic view and swimming pool
Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!
Exterior

Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!

Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!
Hotel San Gregorio
Seasonal outdoor pool, pool loungers

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (104)
"Very nice staff, great service, super clean. Will stay again."
Hotel San Gregorio
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.