Photo by Karen Dean

Search Vacation Homes in Gaiole in Chianti

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Gaiole in Chianti

Borgo Argiano

10.0 out of 10, Exceptional, (69)
"Very comfortable stay. "
$292 nightly
The price is $331
Oct 21 - Oct 22
Total with taxes and fees
Borgo Argiano

Il Palazzetto

9.6 out of 10, Exceptional, (7)
Il Palazzetto

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (142)
"What a view! This location was all that we were hoping for. Thank you! "
Farmhouse in the heart of the real chiantishire

Casa Vacanze Le Case

9.0 out of 10, Wonderful, (8)
"Situata in una posizione ideale per trascorrere un momento di relax accompagnati da una vista eccezionale. Davvero bella location."
$121 nightly
The price is $139
Oct 5 - Oct 6
Total with taxes and fees
Casa Vacanze Le Case

detached villa with private pool and garden

8.8 out of 10, Excellent, (25)
"We had a lovely stay. The house is quit near the village but no to near. It is quiet at night. Any problems were fixed very fast. The house offers wonderful views along with a small but very clean pool. It is very near Siena and Florence which makes it an ideal base for trips"
detached villa with private pool and garden

Agriturismo La Ferrozzola

9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
Agriturismo La Ferrozzola

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (16)
"We were just astounded, and couldn't have asked for anything more. Actually was bigger than we thought. "
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

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

Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

9.8 out of 10, Exceptional, (106)
"Such a beautiful home and beautiful surroundings. The sunset was incredible and counting the stars I was in awe. Thank you Anna for letting us stay in your amazing home. A dip in pool after a day out made it perfect. "
Tuscan villa with infinity salt private pool and jacuzzi on breathtaking view

A wonderful country house in the heart of Chianti

9.8 out of 10, Exceptional, (22)
"We enjoyed a relaxing week in this beautiful apartment surrounded by lush gardens with a view of the Tuscan hills. Our host was charming and welcoming. "
A wonderful country house in the heart of Chianti

Stunning villa for 10 guests with WIFI, A/C, TV, patio and panoramic view

Stunning villa for 10 guests with WIFI, A/C, TV, patio and panoramic view

12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite

10.0 out of 10, Exceptional, (25)
"I can’t give enough stars to this fabulous home! The accomodations were great- great communication with host. We had this as home base for 10 days… a local chef named Serena is available to hire if you book early enough. She prepared three amazing dinners for us! the courtyard in back with the vista of Tuscany was amazing. Miles and miles of vineyards, estates, beautiful gardens. Please book here if you have the chance, a visit of a lifetime! "
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite

The Photographer's House

10.0 out of 10, Exceptional, (11)
"Conveniently located in hilltop town, with multiple (excellent) restaurants within short walking distance. Easy to get to Florence/Siena Autostrada, San Gimignano, etc. Spacious property with garden and views - well equipped. Very enjoyable."
The Photographer's House

Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

9.8 out of 10, Exceptional, (60)
"We spent 3 weeks in Europe from Barcelona to Cadaques to Provence to Cannes to Nice to Monaco to Rome and Castellina in Chianti. Our stay in Stella at this location was our absolute favorite. Federico was very kind kind, greeted us upon arrival, helped us with questions, and gave us suggestions around the area. We highly recommend this place and are already making our plans to return."
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

Farmhouse in old mill nestled in the beautiful Chianti hills

8.8 out of 10, Excellent, (18)
"A beautiful place to stay and very friendly hosts; Roberto and Rafaella will do anything to make your stay unforgettable. The house has everything you need and the pool is nice and beautiful. Lots of nice places to visit in the neighbourhood. I can surely recommend this Farmhouse!!!!"
Farmhouse in old mill nestled in the beautiful Chianti hills

Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence

9.8 out of 10, Exceptional, (33)
"We enjoyed 4 nights in this charming Tuscan villa. Gianna is a lovely person and hostess, and we had more than enough room to relax as a family of four. We enjoyed the sunset views over the olive tree groves, dinners in the cozy dining room, and delicious jam, honey, olive oil and wine, all from our hostess. Thank you, Gianna!"
Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence

[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

Leo&Kira House

10.0 out of 10, Exceptional, (1)
"This beautiful old house in Greve is very charming and true to Italian style, made of stones. The downstairs room is a combination of bedroom and living with a TV, with access to the yard. There is bathroom downstairs. Upstairs has two connected rooms with queen size beds un each and one bathroom. Downstairs there's a good size kitchen with a fridge, stove, and a table. My only issue with the place was that there were no screens on the windows so when you opened them sometimes you'd get flies...
Leo&Kira House

Pet friendly home in Castelfranco Piandiscó

10.0 out of 10, Exceptional, (2)
"We had a very nice time in Castelfranco Piandisco.Elena is very friendly and an excellent host and her house is beautiful. The bedrooms are spacious, The kitchen is small but well equipped. There are several places where you can sit outside including a balconyIt is a peaceful location. The swimming pool is super. A perfect location to unwind and relax with friends or family."
Pet friendly home in Castelfranco Piandiscó

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (8)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
$218 nightly
The price is $223
Oct 8 - Oct 9
Total with taxes and fees
Chianti Craft House Badia a Passignano
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Gaiole in Chianti Hotel Reviews

Find out more about Gaiole in Chianti

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Number of reviews
441
Accommodation
1605 Vacation Homes
Lowest Price
$139
Highest Price
$331

Explore a world of travel with Expedia