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Compare 1369 Vacation Homes in Gaiole in Chianti with updated reviews, rates, and availability.

Borgo Argiano
10.0 out of 10, Exceptional, (58)
"Beautiful property and location in the middle of Tuscany. Small boutique hotel with great pool area, outdoor area that screams relaxation."
Borgo Argiano
Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view
9.8 out of 10, Exceptional, (90)
"We had such a fantastic week staying at this gorgeous villa. A perfect location and setting allowing us all to enjoy some quality family time relaxing in the sun. Thank you"
Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view
Casa Vacanze Le Case
9.0 out of 10, Wonderful, (7)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
The price is $148
includes taxes & fees
$132 per night
Sep 25 - Sep 26
Casa Vacanze Le Case
Podere Baccoleno
10.0 out of 10, Exceptional, (4)
"Incredibly scenic location, neat property, well-equipped, heartly welcome. PERFECT in any way! Thank you Francesca!"
Podere Baccoleno
Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, (127)
"We spent 4 weeks in this house .The owner was very helpfull the house was top notch If You want to ear the silence it is one of the best place House was what were expected and more I recommand this house for people need to relax in peace and calm A special Thanks to the MAMMA"
Farmhouse in the heart of the real chiantishire
Idyllic guest house in Tuscan country house style with swimming pool
10.0 out of 10, Exceptional, (16)
"We had a lovely stay in the Tuscan countryside. The house was well-appointed and Ms. Flaks and her family were excellent hosts. We enjoyed taking a dip in the pool after exploring nearby towns. We also were happy to be greeted by the dogs."
Idyllic guest house in Tuscan country house style with swimming pool
Wonderful Tuscan farmhouse with large spaces and panoramic views
10.0 out of 10, Exceptional, (10)
"Everything was exactly as advertised at this beautiful Impruneta Tuscan farmhouse - perfect spot for two couples to explore Tuscany. Mattia had some excellent recommendations for areas to explore. We had beautiful views of the Tuscan hills. While we had some rainy days, that also meant we had incredible, vibrant, double rainbows appear. Accomodations: The farmhouse is just charming. There is one Jack and Jill bathroom and it has great use of small space with beautiful tile. WiFi worked fine...
Wonderful Tuscan farmhouse with large spaces and panoramic views
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
10.0 out of 10, Exceptional, (51)
"This home was in the perfect spot with wonderful views outside of the windows. The smell of the flowers blooming was wonderful. We absolutely enjoyed our stay. There is a town close by called Travarnelle with everything you need, groceries, restaurants and more. Lucia and Roberto were so quick to respond when needed. They made everything super easy. She went over everything in the house and places to visit as soon as we arrived. They even included a delicious bottle of wine. The house is...
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
Independent house in the hills of the Sienese countryside
10.0 out of 10, Exceptional, (71)
"To begin, this was one the best homes we have had the luck and pleasure to experience. The small house felt like a home. Emanuela, Roberto, and their family were kind, welcoming, and helpful. Their farm and home are a life of love and exacting design and craftsmanship. The necessities are all short drives away; small towns and the larger communes provided learning, great food, history, and art. The stay was relaxing because of the care and attention to detail that the owners supplied in...
Independent house in the hills of the Sienese countryside
Villa with large garden in the Chianti hills
9.4 out of 10, Exceptional, (67)
"This house was in a great, central location for exploring Tuscany. The outside space was beautiful. The pool was great after a long hot day. The house had every thing we needed. It is on a dirt road which surprised us, but wS not a problem."
Villa with large garden in the Chianti hills
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
9.8 out of 10, Exceptional, (69)
"Beautiful house, verandah and great swimming pool - large and deep enough for diving if your teenage kids love this as ours do! The Chianti region is beautiful. Trips to Siena and San Gimignano are a must! "
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
9.8 out of 10, Exceptional, (59)
"The best features of this villa are its outside spaces and fantastic views. We had a great week with wonderful weather and really made the most of being in this stunning location. The villa is up a bumpy dusty track, but once you get used to that, it is quick and easy to get to Castellina in Chianti for provisions, and there is even a great winery and beautiful restaurant at the bottom of the track in Fonterutoli itself - a definite highlight for us. However all was not perfect. Before we...
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Typical Tuscan Country House
10.0 out of 10, Exceptional, (113)
"Nice tidy property with everything we needed for a great stay, great location and lovely and helpful host."
Typical Tuscan Country House
Glicini 1, your holiday home in Chianti just 30 minutes from Florence and Siena
10.0 out of 10, Exceptional, (48)
"What a perfect place to come to and relax. Right from the first interaction with Lucia and Roberto, I knew that my mom and I picked the right place to unwind and enjoy a getaway together. They were absolutely incredible, greeted us with a warm welcome and with their beautiful hearts. I felt like we knew each other for years. I felt comfortable and right at home and that’s exactly what my mom and I were looking for! From the breathtaking grounds, to amazing recommendations, we were so grateful to...
Glicini 1, your holiday home in Chianti just 30 minutes from Florence and Siena
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
9.6 out of 10, Exceptional, (44)
"With just a short walk to town (San Donato), you have fantastic restaurants including La Toppa, bar and small supermarket. Everyone is welcoming and friendly. We really enjoyed dinner at La Toppa, fantastic food and the pizza restaurant in town was excellent too. It is a short drive to other villages, Siena approximately 30 minutes away. The house is homely and relaxing. We had a fantastic enjoyable relaxing stay."
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
A cottage in the middle of the countryside just a stone's throw from the center of Florence<br>
10.0 out of 10, Exceptional, (6)
"We thoroughly enjoyed this beautiful cottage, which has been lovingly built and maintained by Carlo. It is close enough to Florence for easy day trips - a car is recommended for convenient access to the property, but there is ample free parking in a nearby town to head downtown by bus. Accommodations were very comfortable, we made good use of the fridge and convection cooktop, and the views are unmatched. Carlo was kind and quick to respond with any questions we had. Pro tip for those not...
A cottage in the middle of the countryside just a stone's throw from the center of Florence<br>
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
10.0 out of 10, Exceptional, (21)
"We have just returned from a wonderful 10 night stay at Porcilia. The property was exactly as advertised and Francesca was a very welcoming and helpful host. The property was clean and well equipped. The pool was excellent and loved by all our party! The pool and the grounds were all very well maintained! We would highly recommend a stay at Porcilia!!"
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.
8.8 out of 10, Excellent, (10)
"The house has lots of space. We liked the area around and specially Home Restaurant near by the house "
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.
[Chianti] Riccimballa Luxury Penthouse
10.0 out of 10, Exceptional, (1)
"The location is amazing. House is surrounded by hills and valleys. Perfect view of Tuscany. Plenty of amenities. Very spacious and clean house. Stay is on the second floor so be prepared to carry the luggage. There are two bathrooms but only one shower. The shower drain was not properly draining so was a bit of an inconvenience since we were 8. Good for smaller groups. Highly recommend this stay. I was there during the end of March, was a bit chilly but I am sure it will be more beautiful in...
[Chianti] Riccimballa Luxury Penthouse
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Other property types in Gaiole in Chianti

Farmhouse apartment in Chianti with garden and pool for 2 people
9.4 out of 10, Exceptional, (36)
"Wonderful hosts, quiet ancient setting Highly recommend"
Farmhouse apartment in Chianti with garden and pool for 2 people
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
8.8 out of 10, Excellent, (3)
"Property is off the beaten track so very peaceful. La Luna was a little small in the kitchen lounge area for 4 people (needs another sofa). Unfortunately we had a few issues that we told the manager about at the end of our stay in the hope that they will be sorted for future visitors. We couldn’t get the tv to work (only wanted to watch Euro football finals!), dishwasher wouldn’t work and the plug sockets were a nightmare with a need for a lot more adapters or extension leads that would fit the...
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1193)
"Such good value for money! Great location near by Florence with a shuttle bus service makes it an ideal stay for the city!"
The price is $127
includes taxes & fees
$108 per night
Sep 30 - Oct 1
Hu Firenze Camping In Town
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.