Gaiole in Chianti Villas from CA $130

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

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Our top choices for Gaiole in Chianti villas

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

Gaiole in Chianti

Bernard K.

CA $2,457 total

includes taxes & fees

Sep 11 - Sep 12

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

CA $1,842 total

includes taxes & fees

Aug 19 - Aug 20

3. Villa Marcolina

Castelnuovo Berardenga

CA $1,314 total

includes taxes & fees

Aug 13 - Aug 14

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

Radda in Chianti

Amber M.

CA $2,325 total

includes taxes & fees

Sep 1 - Sep 2

Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Monteriggioni

Alvaro

CA $298 total

includes taxes & fees

Aug 13 - Aug 14

6. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

CA $792 total

includes taxes & fees

Sep 3 - Sep 4

7. Rooster House, cooking classes and opera

Toscana

CA $210 total

includes taxes & fees

Aug 14 - Aug 15

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

CA $7,781 total

includes taxes & fees

Aug 14 - Aug 15

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Top Gaiole in Chianti Hotel Reviews

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"Great hotel, around 20 mins drive from Florence so not too far but bear in mind if you’re driving there is a restricted zone. The property is an old mill from the 1300s with a beautiful view over the River Arno. Staff was very friendly and breakfast was very nice - although it’s certainly nothing particularly exceptional, just an ok buffet spread with the usual. The rooms are nice but a little dated (however it’s a really really old building, so some might find this part of the charm). Overall would go back and recommend."

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

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	174
Accommodation	1891 Villas
Lowest Price	CA $130
Highest Price	CA $15,893

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between CA $130 and CA $15,893 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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Search Gaiole in Chianti Villa Rentals from CA $130

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 Marcolina

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

5. Villa Montecastello

6. Villa Il Signorino

7. Rooster House, cooking classes and opera

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

9. Villa Torre Among the Hills of Siena

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

11. Luxury Villa in the Florentine hills

12. Pool Villa - Breakfast included

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

14. Villa Capanna: A Window onto Tuscany

15. Artisti del Cavallo Tourism

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

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

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

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

20. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Hotel Mulino di Firenze, WorldHotels Crafted

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia