Best Gaiole in Chianti Villas: Private & Luxury Villa Accommodations in Gaiole in Chianti

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.

includes taxes & fees

18 Sept - 19 Sept

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 traveller

includes taxes & fees

1 Sept - 2 Sept

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.

includes taxes & fees

17 Sept - 18 Sept

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

5. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

19 Sept - 20 Sept

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

6. Rooster House, cooking classes and opera

Toscana

includes taxes & fees

1 Sept - 2 Sept

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.

includes taxes & fees

1 Sept - 2 Sept

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

8. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

includes taxes & fees

14 Sept - 15 Sept

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Top Gaiole in Chianti Hotel Reviews

Villa I Barronci Resort & Spa

10/10 Excellent

"Great place."

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"WOW! What a beautiful place and awesome hosts! 15 of us traveled to celebrate several birthdays, to enjoy, to discover the area, eat well and create new experiences. For all of these I used the experience and recommendations of Jacopo and Beatrice. We maintained communication for 3 months, and everything turned out perfect! They are the perfect hosts and this is a perfect house whether you want to rest or use it as a base with a large group. The villa(house) is large, with plenty of to do's, with a nice pool and quiet surroundings. The pictures are accurate and the dinners from Beatrice are amazing. Do not hesitate to stay on this place, to pay for the villa and the experiences, and to work together with Jacopo and Beatrice for the perfect celebration and vacation. Don't skip taking a tour of local wineries and eating in one of the local restaurants. 100% Recommended!!"

Hu Firenze Camping In Town

8/10 Good

"The accommodation is very good value for money. Nice facilities. The food in the restaurant is excellent and at a very reasonable price. Just one small complaint. We arrived in a torrential downpour, but had to wander around the site in the dark looking for our chalet. I thought a little buggy to help travellers would be a good idea."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"This is a very special Tuscan style hotel in the beautiful countryside surrounded by vineyards and olive groves. The staff were excellent, special mention goes to Elisa ,and the food was amazing. My only feedback, if you pay for a treatment the other spa facilities should be included. Also, the gym is very small but let's I wasn't there to train."

Poderi Arcangelo

8/10 Good

"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the view and location, but worth noting. Breakfast was nice, we would have preferred a little more choice, but no complaints, they hosted a pizza night on one of our stays, the pizza was ok, we would have preferred to have the Tuscan dinner another night but didn’t work with our plans, All in all a lovely stay, would happily return."

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	248
Accommodation	1552 Villas
Lowest Price	AU$215
Highest Price	AU$7,830

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Expect to pay between AU$215 and AU$7,830 per night for villas in Gaiole in Chianti. Whatever your budget, an awesome stay is just clicks away on Expedia. This price was 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?

Pick from 1552 villas in Gaiole in Chianti. Whether you're travelling with the little ones or planning a getaway with some friends, Expedia can help you find the best space for your crew.

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

Whatever your tastes or interests, Gaiole in Chianti has loads to keep you entertained. Castle of Brolio, Meleto Castle and Castello di Radda Winery are on most visitors' sightseeing plans. Don't head home without exploring Castello di Albola, Badia a Coltibuono and Il Molino di Grace Winery either. With Expedia's hotel deals in Gaiole in Chianti, you can see more terrific attractions like these with the cash you save.

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Change your mind

Treat yourself

Be picky

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. Villa Montecastello

6. Rooster House, cooking classes and opera

7. Villa Il Signorino

8. Villa Capanna: A Window onto Tuscany

9. The San Leonino House

10. Villa Torre Among the Hills of Siena

11. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

12. Luxury Villa in the Florentine hills

13. GuestHost - Porta Romana Elegant House with Private Parking!

14. Il Poggio dell'Eremita

15. Villa with Pool - Two Bedrooms

16. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

17. Villa Sunset, in the heart of Chianti

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

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

20. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Find holiday rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Villa I Barronci Resort & Spa

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia