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Our top choices for Gaiole in Chianti villas

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

1. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is CA $2,424
CA $2,462 total
includes taxes & fees
Nov 15 - Nov 16
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A stone building with a swimming pool, wooden deck, and a tall tree.

2. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
7.4 out of 10, Good, (3 reviews)
"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...
United States
JIm B.
The price is CA $946
CA $1,708 total
includes taxes & fees
Nov 18 - Nov 19
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

3. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is CA $11,218
CA $12,010 total
includes taxes & fees
Nov 12 - Nov 13
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

4. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $2,008
CA $2,358 total
includes taxes & fees
Nov 12 - Nov 13
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

5. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,008
CA $2,358 total
includes taxes & fees
Nov 12 - Nov 13
Villa Torre Among the Hills of Siena
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

6. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is CA $174
CA $196 total
includes taxes & fees
Nov 13 - Nov 14
Rooster House, Cooking Classes, and Opera
A two-story building with balconies, outdoor seating, and potted plants.

7. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is CA $114
CA $132 total
includes taxes & fees
Nov 15 - Nov 16
Artisti del Cavallo Tourism
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

8. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is CA $499
CA $554 total
includes taxes & fees
Nov 18 - Nov 19
Villa Montecastello
A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

9. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
Vaggio
The price is CA $1,663
CA $1,668 total
includes taxes & fees
Nov 15 - Nov 16
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

10. Villa Mami: A Tuscan retreat full of elegance and charm

Villa Mami: A Tuscan retreat full of elegance and charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is CA $3,169
CA $4,116 total
includes taxes & fees
Nov 18 - Nov 19
Villa Mami: A Tuscan retreat full of elegance and charm
A modern outdoor pool area with a stone structure, a covered seating area, and a view of distant mountains.

11. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Vaggio
The price is CA $963
CA $968 total
includes taxes & fees
Nov 12 - Nov 13
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

12. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is CA $220
CA $242 total
includes taxes & fees
Nov 17 - Nov 18
Il Poggio dell'Eremita
A house with a covered patio, a lawn, and potted plants.

13. Villa 'Cascina Gretaio' with Mountain Views, Private Pool and Wi-Fi

Villa 'Cascina Gretaio' with Mountain Views, Private Pool and Wi-Fi
Reggello
The price is CA $870
CA $957 total
includes taxes & fees
Nov 13 - Nov 14
Villa 'Cascina Gretaio' with Mountain Views, Private Pool and Wi-Fi
A stone building with a tower, surrounded by trees and a garden.

14. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is CA $1,389
CA $1,739 total
includes taxes & fees
Nov 12 - Nov 13
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A large estate with a swimming pool, tennis court, and multiple guest rooms.

15. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is CA $18,696
CA $18,696 total
includes taxes & fees
Nov 29 - Nov 30
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

16. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is CA $22,436
CA $22,436 total
includes taxes & fees
Nov 12 - Nov 13
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
impruneta
10.0 out of 10, Exceptional, (117 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is CA $1,775
CA $2,030 total
includes taxes & fees
Nov 13 - Nov 14
Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

18. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Rignano sull'Arno
The price is CA $4,563
CA $7,797 total
includes taxes & fees
Nov 13 - Nov 14
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

19. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is CA $2,060
CA $2,234 total
includes taxes & fees
Nov 29 - Nov 30
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A residential area with a swimming pool, stone walls, and a view of houses and hills.

20. Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning

Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
Vaggio
The price is CA $960
CA $965 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
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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Learn more about Gaiole in Chianti

Medieval stone buildings house family-run wine shops where you can taste Chianti Classico from surrounding vineyards. Join locals at Piazza Ricasoli's cafés before exploring L'Eroica cycling route that winds through nearby hilltop villages.

See all hotels in Gaiole in Chianti
A stone castle with battlements overlooking a lush valley with vineyards.

Frequently Asked Questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between CA $113 and CA $22,435 per night. Whatever your budget, you'll find something that fits the bill with Expedia. 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 Gaiole in Chianti?

Gaiole in Chianti has villas to select from. Find your perfect stay quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.

Why book your villa in Gaiole in Chianti with Expedia?

We think vacation time shouldn't be complicated, so if you're looking for villas at a nice price, Expedia can help. Save those pennies and opt for an all-inclusive stay, or splurge on a luxury villa to spoil your loved ones. Use our convenient search filters to find an escape in Gaiole in Chianti that suits your needs.

How can I find cheap villas in Gaiole in Chianti?

An excellent way to locate cheap villas in Gaiole in Chianti is with Expedia's filter tool. Narrow your search by star rating, amenities and budget to nab unbeatable rates in only a click or two.

What is there to do near my villa in Gaiole in Chianti?

There are plenty of fantastic things to do in Gaiole in Chianti. Make tracks to leading attractions like Cantalici Winery, Castle of Brolio and Meleto Castle. Badia a Coltibuono, Church of San Sigismondo and PoggioBrandani also appeal to many visitors.