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

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 Tub, and Wi-Fi

Gaiole in Chianti

Bernard K.

$2,768 nightly

Oct 4 - Oct 5

Total with taxes and fees

An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

2. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Gaiole in Chianti

"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"

Anonymous traveler

$1,278 nightly

Oct 12 - Oct 13

Total with taxes and fees

An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

3. Villa Bellavista - Homelike Villas

Montegonzi

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

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

Radda in Chianti

Amber M.

$1,108 nightly

Sep 23 - Sep 24

Total with taxes and fees

A stone building with a wooden door, surrounded by greenery and overlooking a valley.

5. Stunning villa with large pool in the heart of Chianti 12km from Siena

Radda in Chianti

ana r.

6. Villa Montecastello

Monteriggioni

Alvaro

$172 nightly

Sep 20 - Sep 21

Total with taxes and fees

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.

7. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

$515 nightly

Sep 17 - Sep 18

Total with taxes and fees

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

8. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

$148 nightly

Sep 19 - Sep 20

Total with taxes and fees

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Top Gaiole in Chianti Hotel Reviews

Villa Olmi Firenze

10/10 Excellent

"N/A"

Fattoria di Vegi

10/10 Excellent

"What an amazing hotel. The attention to detail on the refurb of the property is phenomenal. Once the tennis court, spa etc are completed this will easily be high hundreds per night. We visited all the other properties in the surrounding area and nothing came close to this hotel. The food and drinks were also brilliant - best meal we had in Tuscany was in the hotel. My only suggestions would be to rotate the staff more - they seemed slightly over worked. Easily one of the best hotels I have stayed in."

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."

Hu Firenze Camping In Town

8/10 Good

"It took awhile for staff to find our reservation through Expedia, we weren’t sure if it even existed on their end.. It’s about an hour walk to the city center, but bus, bike, taxi options are available. The staff were rude when we struggled to buy smokes from the machine in reception (if you don’t have European ID, good luck!). Our porch light didn’t work in our glamp tent and it wasn’t the best quality but amenities make it worth it- shops, restaurant, pool/jacuzzi, laundry, etc., though it doesn’t seem the pool is open in early September."

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"

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Gaiole in Chianti Villas information

Number of reviews	239
Accommodation	1891 Villas
Lowest Price	$151
Highest Price	$8,093

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between $151 and $8,093 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 1891 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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Villas in Gaiole in Chianti

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Upfront pricing

Check prices for these dates

Our top choices for Gaiole in Chianti villas

1. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

2. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

3. Villa Bellavista - Homelike Villas

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

5. Stunning villa with large pool in the heart of Chianti 12km from Siena

6. Villa Montecastello

7. Villa Il Signorino

8. Rooster House, cooking classes and opera

9. Villa Capanna: A Window onto Tuscany

10. Villa Torre Among the Hills of Siena

11. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

12. Luxury Villa in the Florentine hills

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

14. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

15. Villa Sunset, in the heart of Chianti

16. Il Poggio dell'Eremita

17. Villa with Pool - Two Bedrooms

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

19. My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

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

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Top Gaiole in Chianti Hotel Reviews

Villa Olmi Firenze

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia