A stone castle with battlements overlooking a lush valley with vineyards.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 SAR 7,543
SAR 7,644 total
includes taxes & fees
3 Nov - 4 Nov
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
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is SAR 4,232
SAR 6,247 total
includes taxes & fees
1 Nov - 2 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A patio with a grill, a table, chairs, and a potted plant.

3. 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 SAR 4,036
SAR 4,049 total
includes taxes & fees
11 Nov - 12 Nov
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

4. 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 SAR 666
SAR 745 total
includes taxes & fees
16 Oct - 17 Oct
Villa Montecastello
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

5. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is SAR 1,467
SAR 2,049 total
includes taxes & fees
1 Nov - 2 Nov
Villa Il Signorino
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 SAR 461
SAR 549 total
includes taxes & fees
15 Oct - 16 Oct
Rooster House, cooking classes and opera
A stone building with a tower, surrounded by trees and a garden.

7. 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 SAR 3,900
SAR 4,826 total
includes taxes & fees
17 Oct - 18 Oct
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

8. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is SAR 5,627
SAR 6,553 total
includes taxes & fees
17 Oct - 18 Oct
Villa Torre Among the Hills of Siena
A two-story building with balconies, outdoor seating, and potted plants.

9. 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 SAR 304
SAR 351 total
includes taxes & fees
22 Oct - 23 Oct
Artisti del Cavallo Tourism
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

10. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (72 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is SAR 565
SAR 657 total
includes taxes & fees
15 Oct - 16 Oct
Il Poggio dell'Eremita
A white shelving unit with various decorative items and framed pictures.

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 SAR 2,523
SAR 2,535 total
includes taxes & fees
2 Nov - 3 Nov
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
A house with a covered patio, a lawn, and potted plants.

12. Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi

Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
Reggello
The price is SAR 2,555
SAR 2,832 total
includes taxes & fees
1 Nov - 2 Nov
Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

13. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (151 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
Luxury Villa in the Florentine hills
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

14. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is SAR 8,381
SAR 11,461 total
includes taxes & fees
13 Nov - 14 Nov
Villa Mami: A Tuscan Retreat of Elegance and Charm
A residential area with a swimming pool, stone walls, and a view of houses and hills.

15. 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 SAR 2,271
SAR 2,283 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
A stone building with a large arched entrance, potted plants, and outdoor seating.

16. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 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 SAR 4,110
SAR 4,709 total
includes taxes & fees
26 Oct - 27 Oct
Exclusive Estate | Personal Concierge & Heated Pool
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

17. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is SAR 5,627
SAR 6,553 total
includes taxes & fees
17 Oct - 18 Oct
Villa Capanna: A Window onto Tuscany
Terrace/patio

18. Villa Sunset, in the heart of Chianti area

Villa Sunset, in the heart of Chianti area
Greve in Chianti
8.0 out of 10, Very good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti area
A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

19. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

20. 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 SAR 7,124
SAR 8,071 total
includes taxes & fees
8 Nov - 9 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
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 Gaiole in Chianti Hotel Reviews

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"It was a really nice experience staying at Hu Firenze. It was away from the hustle and bustle of the city and the main tourist areas, while a bus stop right across the street made it easy to get to the city centre. We also got to enjoy a bit of the Tuscan countryside experience. The only issue was that there is another Hu campsite called Hu Certosa, so you need to be careful not to book the wrong one, especially when travelling in a group and everyone is booking separately. This happened to us, but fortunately, the staff allowed my brother to stay with us since our accommodation had an extra bed. However, we had already paid for a tent at Hu Certosa. My recommendation would be to start breakfast earlier than 7:30 a.m. This would allow guests to leave at different times and help avoid long queues at the bus stop."
Shahram 3-night trip
Posted 5 hours ago
Hu Firenze Camping In Town

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between SAR 351 and SAR 11,461 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 1822 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?
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