Gaiole in Chianti Villas Rentals

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

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Our top choices for Gaiole in Chianti villas

An outdoor patio with a stone wall, a wooden bench, a cushioned sofa, and umbrellas providing shade.

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

Gaiole in Chianti

Bernard K.

$1,719 nightly

Nov 15 - Nov 16

Total with taxes and fees

A stone building with a swimming pool, wooden deck, and a tall tree.

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

Radda in Chianti

"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...

JIm B.

$1,191 nightly

Nov 15 - Nov 16

Total with taxes and fees

A long wooden table set for a meal with a view of a hillside town.

3. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

$8,407 nightly

Nov 14 - Nov 15

Total with taxes and fees

A stone building with a tiled roof, surrounded by a well-maintained lawn and trees.

4. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

$1,646 nightly

Nov 14 - Nov 15

Total with taxes and fees

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

5. Villa Torre Among the Hills of Siena

Vico dʼArbia

$1,646 nightly

Nov 15 - Nov 16

Total with taxes and fees

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

6. Rooster House, Cooking Classes, and Opera

Tavarnelle Val di Pesa

$134 nightly

Nov 14 - Nov 15

Total with taxes and fees

A two-story building with balconies, outdoor seating, and potted plants.

7. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

$80 nightly

Nov 15 - Nov 16

Total with taxes and fees

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

8. Villa Montecastello

Monteriggioni

Alvaro

$317 nightly

Dec 5 - Dec 6

Total with taxes and fees

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

Vaggio

$1,164 nightly

Nov 16 - Nov 17

Total with taxes and fees

A large estate with multiple buildings, a swimming pool, and surrounding olive groves.

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

Toscana

$2,888 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Vaggio

$674 nightly

Nov 15 - Nov 16

Total with taxes and fees

A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

12. Il Poggio dell'Eremita

Sinalunga

Paul Q.

$167 nightly

Nov 20 - Nov 21

Total with taxes and fees

A house with a covered patio, a lawn, and potted plants.

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

Reggello

$664 nightly

Nov 14 - Nov 15

Total with taxes and fees

A narrow road leading to a stone building with arched doorways, surrounded by olive trees and greenery.

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

Vico dʼArbia

Marina O.

$1,213 nightly

Nov 14 - Nov 15

Total with taxes and fees

A large estate with a swimming pool, tennis court, and multiple guest rooms.

15. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

$13,088 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

Firenze

$15,705 nightly

Nov 14 - Nov 15

Total with taxes and fees

A stone building with a large arched entrance, potted plants, and outdoor seating.

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

impruneta

Oli P.

$1,401 nightly

Nov 14 - Nov 15

Total with taxes and fees

A rectangular swimming pool with lounge chairs and a pergola, surrounded by a landscaped garden and a mountain backdrop.

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

Rignano sull'Arno

$5,477 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

Montespertoli

Krista G.

$1,553 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

Vaggio

$672 nightly

Nov 14 - Nov 15

Total with taxes and fees

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Top Gaiole in Chianti Hotel Reviews

Hotel Athena

10/10 Excellent

"Staff are very friendly and helpful. We appreciated the valet parking at no extra charge. Great location and stunning views from the terrace bar. The staff made it one of the best hotels we have stayed at in a very long time. Good value for the price."

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	250
Accommodation	1822 Villas
Lowest Price	$93
Highest Price	$15,705

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between $93 and $15,705 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?

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.

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Things to do in Gaiole in Chianti

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Room 1

Check prices for these dates

Our top choices for Gaiole in Chianti villas

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

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