Gaiole in Chianti Villas - Best Villa Gaiole in Chianti 2026

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

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Our top choices for Gaiole in Chianti villas

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

Gaiole in Chianti

"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "

Ravin N.

includes taxes & fees

15 Aug - 16 Aug

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

Villa Marcolina

Castelnuovo Berardenga

includes taxes & fees

17 Jul - 18 Jul

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

Rignano sull'Arno

includes taxes & fees

14 Aug - 15 Aug

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

19 Jul - 20 Jul

Luxury Villa in the Florentine hills

Florence

edward p.

includes taxes & fees

19 Jul - 20 Jul

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

Rignano sull'Arno

includes taxes & fees

19 Jul - 20 Jul

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

Rignano sull'Arno

includes taxes & fees

17 Jul - 18 Jul

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Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Gorgeous hotel, amazing views. Fabulous staff. They made our stay in Siena extra special."

Radisson Blu Hotel, Florence

10/10 Excellent

"I had a wonderful stay. The room was impeccably clean, and the bed was very large and comfortable. The bathroom was especially spotless and well maintained. The continental breakfast was delicious with a great variety of options. Most of all, the staff was outstanding. Everyone was extremely friendly, welcoming, and always willing to help. I would definitely stay here again and highly recommend this hotel to other travelers."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"Borgo refers to something like little village and that’s what this property is. A cluster of beautiful stone buildings and gravel drives surrounded by acres of olive and lavender. Beautifully appointed common and areas in rooms. Excellent restaurant with elevated cuisine. Beautiful pool. Distance skyline view of Sienna, Really no negatives. Would definitely come back."

Villa I Barronci Resort & Spa

10/10 Excellent

"An amazing place to stay and relax in Florence. Highly recommend if you want a place to relax and away from the crowds . The staff was very respectful, polite and accommodating. Breakfast was amazing especially the chocolate croissants. Great value for the price. Thank you villa I Barronci!"

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"Such a lovely property! The grounds are beautiful and having a pool to use after a hot day of walking around is wonderful. We found our dinner in the restaurant to be excellent! Good breakfast buffet! The only slight downside is if you want to go into Florence every day, while they do offer a shuttle, it stops quite a walk from the centre of town and the schedule isn’t always convenient so we needed up taking taxis a lot which added up financially. Still worth the area and the hotel but be aware of location. We loved it!"

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	264
Accommodation	1886 Villas
Lowest Price	€124
Highest Price	€1,847

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between €124 and €1,847 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 1886 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 holiday 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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Treat yourself

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Check prices for these dates

Our top choices for Gaiole in Chianti villas

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