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

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Gaiole in Chianti villas

Property grounds

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

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"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. "
United States
Ravin N.
The price is AED 3,020
AED 3,121 total
includes taxes & fees
24 Jul - 25 Jul
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Outdoor dining

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

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very Good, (1 review)
"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!"
Italy
Anonymous traveler
The price is AED 5,116
AED 5,900 total
includes taxes & fees
7 Aug - 8 Aug
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is AED 2,952
AED 3,280 total
includes taxes & fees
16 Jul - 17 Jul
Villa Marcolina
Exterior

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

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is AED 3,206
AED 3,527 total
includes taxes & fees
18 Jul - 19 Jul
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is AED 644
AED 721 total
includes taxes & fees
21 Jul - 22 Jul
Villa Montecastello
Outdoor dining

Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (147 reviews)
"Beautiful property and great experience "
United States
edward p.
The price is AED 839
AED 1,414 total
includes taxes & fees
19 Jul - 20 Jul
Luxury Villa in the Florentine hills
Exterior

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is AED 1,902
AED 2,093 total
includes taxes & fees
16 Jul - 17 Jul
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Exterior

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

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is AED 2,330
AED 2,563 total
includes taxes & fees
17 Jul - 18 Jul
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Outdoor dining

Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is AED 6,479
AED 7,406 total
includes taxes & fees
18 Jul - 19 Jul
Villa Capanna: A Window onto Tuscany
Outdoor dining

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Wunderschönes charmantes, rustikales Ferienhaus in der wunderschönen Toskana. Tolle Lage, sehr freundlicher und charmanter Gastgeber. Senore Guidi und seine Ehefrau sind zauberhafte Gastgeber. Sehr hilfsbereit und zuvorkommend! Die Fotos der Unterkunft stimmen zu 100% überein! Toller Poolbereich. Senor Guidi hat zur Wein- und Olivenöl -Verkostung eingeladen und uns auf Anfrage zu einer persönlichen Begehung seiner Oliven-und-Weinberge mitgenommen. Sehr persönliche und menschliche...
Germany
Anonymous traveler
The price is AED 1,753
AED 1,934 total
includes taxes & fees
18 Jul - 19 Jul
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Pool

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is AED 1,586
AED 1,766 total
includes taxes & fees
19 Jul - 20 Jul
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Exterior

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Saltino
The price is AED 2,750
AED 4,218 total
includes taxes & fees
18 Jul - 19 Jul
Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is AED 415
AED 503 total
includes taxes & fees
17 Jul - 18 Jul
Rooster House, cooking classes and opera
Exterior

La Dimora di Teresa: fairytale house in the woods, ideal for families with children.

La Dimora di Teresa: fairytale house in the woods, ideal for families with children.
Sovicille
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful house for our family. Spacious and well appointed home with a charming rustic feel. It is a short drive to Siena. Marina is super helpful with any need you may have. We had a local chef come to the house to make pizzas for us one evening. It was terrific. Our family enjoyed the peace and quiet of this home in the middle of a busy trip around Italy."
United States
Ericka B.
The price is AED 2,261
AED 3,755 total
includes taxes & fees
23 Jul - 24 Jul
La Dimora di Teresa: fairytale house in the woods, ideal for families with children.
Exterior

Romantic stylish villa with private pool & splendid view

Romantic stylish villa with private pool & splendid view
Panzano In Chianti
9.8 out of 10, Exceptional, (24 reviews)
"Beautiful location with spectacular views."
United States
lawrence s.
Romantic stylish villa with private pool & splendid view
Exterior

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

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is AED 3,069
AED 4,109 total
includes taxes & fees
18 Jul - 19 Jul
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is AED 1,321
AED 1,888 total
includes taxes & fees
16 Jul - 17 Jul
Villa Il Signorino
Exterior

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (68 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
Il Poggio dell'Eremita
Pool

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

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is AED 5,730
AED 7,747 total
includes taxes & fees
19 Jul - 20 Jul
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

Casale Le Rondini with a swimming pool and private garden

Casale Le Rondini with a swimming pool and private garden
LUCIGNANO
Casale Le Rondini with a swimming pool and private garden
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Gorgeous hotel, amazing views. Fabulous staff. They made our stay in Siena extra special."
Seth 2-night trip
Posted 1 hour ago
Grand Hotel Continental Siena – Starhotels Collezione

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between AED 503 and AED 7,747 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 1879 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.