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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Chiusdino

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Relax by the serene pool surrounded by a well-maintained walkway and picturesque views.

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

10.0 out of 10, Exceptional, (96)
"Outstanding lodging and within 10 minutes from the San Gimignano City/Center. Side trips were enjoyable and easy to explore. The accommodations in a country villa were very comfortable and our host Alessandro Martini was great to work with. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Relax by the serene pool surrounded by lush greenery and mature trees.

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

10.0 out of 10, Exceptional, (80)
"Great place. Great host Driveway….needs work "
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Relax in a serene outdoor space with a lush landscape view, a pool, and comfortable seating.

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (110)
"We had a large group of family and friends comfortably stay here. The host was very available and helpful, and personally showed us around the property upon our arrival. The property description is accurate. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Villa Costa, Stunning Villa in the heart of Tuscany.
Situated in a rural countryside setting, this charming home features a traditional stone building with a sloped roof.

Villa Costa, Stunning Villa in the heart of Tuscany.

10.0 out of 10, Exceptional, (36)
"You have all the amenities of a large, historic villa - and also the real farmland all around you. Sheep, horses, dogs - beautiful, and not in your personal space (unless you want them to be!). Pasqualina and her son Francesco are perfect hosts. Incredibly responsive, even with a language barrier. If I return to Tuscany I would want to stay here again. Thank you so much."
Villa Costa, Stunning Villa in the heart of Tuscany.
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Relax in a serene outdoor space surrounded by lush greenery and a tranquil body of water.

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (103)
"Beautiful home, beautiful views. "
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Enjoy the serene view of rolling hills and a distant hilltop structure from this charming balcony.

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (107)
"We had a lovely stay at the villa. The villa was comfortable, well furnished and had a beautiful view of San Gimignano. The owner was very helpful and responsive. We will definitely stay there again if we visit San Gimignano."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Relax by the serene pool surrounded by lush greenery and comfortable lounge seating.

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (7)
"Fabulous place to stay with a big group of family and friends. Very easy walk to town and the beautiful treasures of Siena."
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Relax beneath the pergola's shade, surrounded by lush greenery and a serene pool.

Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa

10.0 out of 10, Exceptional, (42)
"Great Villa to stay at. Owner was excellent to deal with."
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Stunning Villa: 24 guests, private SwimmingPool
Experience the serene atmosphere of our traditional garden, surrounded by a variety of plants and a small pond.

Stunning Villa: 24 guests, private SwimmingPool

9.8 out of 10, Exceptional, (28)
"We had a fantastic time at the house, Fabio was excellent in his communication and help. The house is great with separate areas but big communal spaces. We had a couple of delicious meals cooked for us by Fabio, I would highly recommend this luxury! If I had to say one thing it would be great if the pool seating area was tiled instead of grass, but overall can't fault it."
Stunning Villa: 24 guests, private SwimmingPool
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Experience the tranquility of this Mediterranean-style villa, surrounded by lush gardens and a serene landscape.

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (25)
"We celebrated our baby turning 1 with family and friends and this property was an absolute dream! It comfortably fit our large group! We had a private chef host a dinner for us that Alessandro requested which was incredible! We are grateful for the family memories and would 100% return! Thank you for being such a great host! "
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Luxury Villa Basilio Chianti
Seasonal outdoor pool

Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Standalone residence with a traditional Mediterranean architectural style, surrounded by lush greenery.

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (53)
"The house was fantastic and had more than enough space for our large family. What was particularly great was the large table where we always ate before we went to the very large swimming pool."
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Villa with unique view of Siena with private pool
Stroll through the beautifully maintained garden, featuring a variety of flowering plants and a charming, rustic building with an arched doorway.

Villa with unique view of Siena with private pool

10.0 out of 10, Exceptional, (6)
"I booked Letizia's amazing Villa for a week-long birthday celebration and we loved every minute of our time in the Tuscan sun! It was great to be able to relax by the pool in the peace of the countryside amongst the olive groves while still being only a short walk away from Siena, we just wish we could have stayed for longer!"
Villa with unique view of Siena with private pool
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Relax by the pool with comfortable lounge chairs and a wicker basket for your essentials.

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

8.0 out of 10, Very good, (1)
"We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend."
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Exclusive Farmhouse Pool & View of San Gimignano
Enjoy a romantic dinner for two in this charming outdoor dining area with a round table and wicker chairs.

Exclusive Farmhouse Pool & View of San Gimignano

10.0 out of 10, Exceptional, (1)
Exclusive Farmhouse Pool & View of San Gimignano
Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Relax in a serene outdoor space surrounded by lush greenery and cypress trees, with a patio, lounge chairs, and a swimming pool.

Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena

10.0 out of 10, Exceptional, (2)
"This was the epitome of staying in an authentic Villa, with amazing views of the Tuscany countryside. "
Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14
Relax by the serene pool surrounded by lush greenery and mature trees.

Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14

9.8 out of 10, Exceptional, (7)
"My family and I stayed here for almost a full week in the spring, and had an amazing time. The host was extremely responsive about the check-in process leading up to the stay, during the stay whenever we had any issues, and even after our stay when we needed to recover an item that was left behind. There were some slight hiccups with the house during our stay (garage door opener was out of batteries one time and the shower drain clogged one time), but the host was proactive as can be and quick...
Villa in Colle Di Val D’elsa with 7 bedrooms sleeps 14
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Guest rooms offer spaces with doors and windows, often accompanied by outdoor seating areas.

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

9.8 out of 10, Exceptional, (97)
"Peaceful, quiet, tucked away beautiful in the beautiful Tuscany area. Would stay there again. Excellent property!"
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Villa Panizzi – Villa with private pool
Relax by the pool in a serene outdoor space with a shaded patio, comfortable seating, and lush surroundings.

Villa Panizzi – Villa with private pool

9.4 out of 10, Exceptional, (21)
"Lots of space to spread out and different eating areas. Pool was lovely. A good base for sightseeing and a short hop into San gimignano for an aperitif."
Villa Panizzi – Villa with private pool
Independent RELAX villa 2-5 people 12 min from the sea
Enjoy a meal al fresco on the patio, surrounded by lush greenery and a serene garden.

Independent RELAX villa 2-5 people 12 min from the sea

9.8 out of 10, Exceptional, (18)
"Die Vermieter waren überaus freundlich und sehr hilfsbereit. Die Ausstattung des Hauses ist sehr gut. Man kann sein Auto auf privatem Grund abstellen. Das Haus bietet einer Familie einen sehr ruhigen Urlaub, man ist trotzdem in 10 Minuten in der Altstadt oder in 5 Minuten beim sehr gut ausgestatteten Supermarkt COOP. "
Independent RELAX villa 2-5 people 12 min from the sea
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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Top Chiusdino Hotel Reviews

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Our stay at Castello di Fonterutoli Wine Resort was full of charm and relaxation. The setting in the heart of Chianti is picture-perfect, surrounded by rolling vineyards and peaceful countryside views. The sunsets here were absolutely stunning, painting the hills in warm golden light. One of my favorite parts was ending each day with a relaxing bath in the beautiful tub—it added such a special touch to the stay. Dinner and breakfast at the resort were a real treat, with fresh, flavorful dishes and local wines that made each meal memorable. The staff were very gracious and made us feel so welcome. It’s the perfect place to slow down, enjoy incredible food and wine, and soak in the beauty of Tuscany."
Girish 2-night trip
Posted 1 day ago
Castello di Fonterutoli Wine Resort