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Compare 447 Villas in Chianti Region with updated reviews, rates, and availability.

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Exterior
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
10.0 out of 10, Exceptional, (104)
"we had an amazing week at this villa with 18 family members, age 6 months to 87 years. Jacobo and Beatrice were so nice , very welcoming and super helpful with transportation and amenities nearby. If we had any problems we could easily text and Jacopo would immediately answer . i would recommend coming here ! Faboulous"
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
View of the Villa from garden-pool
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
Outdoor dining
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
10.0 out of 10, Exceptional, (32)
"Villa Il Forte is the most incredible setting. It is an incredible historic and luxurious home while being comfortable, spacious and accommodating. Many different spaces to relax, connect and play. Paolo’s team were absolutely amazing. The chef Thomas is so talented while also being wonderfully personable and fun. The driver Fabrizio was so generous and thoughtful. His guides were knowledgeable and friendly. I have already booked it for next year! I can’t wait to go back! "
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
Your panoramic house in Tuscany between vineyards and olive groves.
Your residence in Tuscany
Your panoramic house in Tuscany between vineyards and olive groves.
9.8 out of 10, Exceptional, (32)
"Lovely property, very comfortable. Good location to explore Tuscany. There is an excellent supermarket less than 10 minutes away. Families would be very comfortable here."
Your panoramic house in Tuscany between vineyards and olive groves.
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Pool
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
10.0 out of 10, Exceptional, (46)
"This place exceeded all of our expectations. The host and his family were amazing and very accommodated. Perfect size for two couples. Bedrooms and bathrooms were private. The location was perfect. We were able to take daily trips everywhere in Tuscany between 15 minutes and one hour. The house and pool were even better than the pictures portray. The place came stocked with everything you need For your vacation. If ever back in Tuscany I would definitely stay here again."
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Luxury Villa with large pool close to Florence
Pool
Luxury Villa with large pool close to Florence
10.0 out of 10, Exceptional, (62)
"Beautiful, historic villa with a fantastic view of the valley below. Our hosts were friendly, helpful and entertaining as well. The icing on the cake was Fonsi's providing breakfast and cooking dinners as requested. Her chef skills were more than we could ask for. "
Luxury Villa with large pool close to Florence
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Pool
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
9.6 out of 10, Exceptional, (17)
"Our 2-wk. reservation (Oct. 5-19) was actually increased by a week Sept. 28-Oct. 5, making it a 3-wk reservation, however, due to a medical issue, we had to return to the USA 10 days early. Gabriella was a wonderful property manager assisting us with seeking medical and hospital care. Lovely property and location."
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Molino del Ponte, Radda in Chianti, Italy
Aerial view
Molino del Ponte, Radda in Chianti, Italy
9.6 out of 10, Exceptional, (5)
"En un mot.. parfait "
Molino del Ponte, Radda in Chianti, Italy
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
Pool
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
10.0 out of 10, Exceptional, (7)
"The house was great and Paula and Niccolo the best. Not a lot of restaurants nearby and you need to make reservations, but about 15 minuntes to Florence."
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
La Merlaia Beauty and Quietness with Pool on Hills of Florence
Pool
La Merlaia Beauty and Quietness with Pool on Hills of Florence
8.8 out of 10, Excellent, (31)
"We were a group of 10 people and the villa was perfect for us. From the beautiful garden and the great pool you have a unique view. The house is charming, with antique furniture, tile floors, and beautiful views, the bedrooms are very large, much more than it seems from the photographs. We found the house perfectly clean and equipped with everything we could possibly need. You can sit down to eat in the kitchen and living room as well as in the patio with many people around the table. Thank you...
La Merlaia Beauty and Quietness with Pool on Hills of Florence
Villa Radda by MMega
Exterior
Villa Radda by MMega
10.0 out of 10, Exceptional, (6)
" We had an incredible stay in this charming villa. There was plenty of room for our family of eight. We were welcomed by our host, David , who responded to our every need. He arranged a special wine tasting for us with delicious cheese and charcuterie . We enjoyed the beautiful pool and the lovely scenery. The town of Gaiole in Chianti was an easy car ride to enjoy a morning cappuccino or an amazing dinner at the local restaurants. We explored the many places and wineries in the area and...
Villa Radda by MMega
VILLA GIOTTO, FLORENCE
Pool
VILLA GIOTTO, FLORENCE
9.4 out of 10, Exceptional, (3)
"The villa was great. My family and I had a fantastic time. Lorenzo was the perfect host. Always there when needed to help with a dinner reservation or to answer questions about how to do something or where to go. If you want Italian charm...this is it. And the pool was spectacular. I can't recommend more highly."
VILLA GIOTTO, FLORENCE
Villa - PrivatePool, Fenced Garden 6000m², 3rooms 8-people, Chianti-Wine-Relax
Pool
Villa - PrivatePool, Fenced Garden 6000m², 3rooms 8-people, Chianti-Wine-Relax
9.8 out of 10, Exceptional, (63)
"Stay was wonderful. Host met us upon arrival and explained everything to us. The only small comment would be that a regular toaster would be nice. "
Villa - PrivatePool, Fenced Garden 6000m², 3rooms 8-people, Chianti-Wine-Relax
Apartments Florence - Villa Fonte Morgana with pool
Backyard with pool
Apartments Florence - Villa Fonte Morgana with pool
10.0 out of 10, Exceptional, (1)
"What a beautiful villa! We thoroughly enjoyed our stay in Tuscan countryside. All rooms were comfortable and large. We were surprised by the lack of body soap and shampoo."
Apartments Florence - Villa Fonte Morgana with pool
Macia Viva, Castellina in Chianti, Siena and Chianti
Pool
Macia Viva, Castellina in Chianti, Siena and Chianti
8.0 out of 10, Very Good, (2)
"The views were beyond compare! Proximity to Castellina in Chianti was wonderful and the management team were responsive to a few issues. My main comment would be, especially considering the rental cost, that the furniture and kitchen supplies (dishes etc) needs upgrading and the quality of the beds/linens should be improved. Overall however, it was a lovely stay! Grazie."
Macia Viva, Castellina in Chianti, Siena and Chianti
Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy
Exterior
Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy
Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy
Beautiful private villa with WIFI, private pool, TV, patio, panoramic view, parking, close to Siena
Building Exterior, Pool
Beautiful private villa with WIFI, private pool, TV, patio, panoramic view, parking, close to Siena
10.0 out of 10, Exceptional, (15)
Beautiful private villa with WIFI, private pool, TV, patio, panoramic view, parking, close to Siena
Private Villa with WIFI, A/C, private pool, hot tub, TV, panoramic view, parking, close to Florence
Pool
Private Villa with WIFI, A/C, private pool, hot tub, TV, panoramic view, parking, close to Florence
9.8 out of 10, Exceptional, (26)
"The house was stunning, even better than the pictures! Marco was a fantastic host, super accommodating and hopeful. I would highly recommend this house to anyone. We truly enjoyed our stay."
Private Villa with WIFI, A/C, private pool, hot tub, TV, panoramic view, parking, close to Florence
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
View from the dining room table
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Exterior
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
9.4 out of 10, Exceptional, (58)
"Beautiful location!"
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
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 Chianti Region

Hu Norcenni Girasole Village
Exterior
Hu Norcenni Girasole Village
4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village
Camping Village Il Poggetto
Front of property
Camping Village Il Poggetto
3.0 star property
8.0 out of 10, Very Good, (41)
"Nice safe village with restaurant, bar and pool. Staff were excellent. "
Camping Village Il Poggetto
Villa Il Palagio
Outdoor pool
Villa Il Palagio
8.8 out of 10, Excellent, (48)
"Thank you all is perfect"
Villa Il Palagio
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.

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region range between and per night. These getaways provide the privacy of your own space at a price that’s friendly to your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Chianti Region?
Chianti Region has 447 villas to pick from. Enter your destination and dates and get a start on planning your dream getaway today.
Why book your villa in Chianti Region with Expedia?
We think organizing a vacation shouldn’t be difficult, so if you’re searching for villas at a great price, Expedia delivers. Stick to the budget and select an all-inclusive stay, or splurge on a luxe villa to spoil your loved ones. Take advantage of our search filters to find an escape in Chianti Region that suits you best.
How can I find cheap villas in Chianti Region?
A fantastic way to zero in on cheap villas in Chianti Region is with Expedia’s easy-to-use filter tool. Refine your search results by star rating, budget and amenities to land unbeatable prices in only a few clicks.