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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Gaiole in Chianti villas

Pool
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Gaiole in Chianti
The price is SAR 25,967
SAR 28,149 total
includes taxes & fees
10 Feb - 11 Feb
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Property grounds
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"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, (8 reviews)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is SAR 4,544
SAR 4,649 total
includes taxes & fees
11 Jan - 12 Jan
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior
Artisti del Cavallo Tourism

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
3.0 star property
Foiano della Chiana
8.4 out of 10, Very Good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is SAR 304
SAR 343 total
includes taxes & fees
13 Jan - 14 Jan
Artisti del Cavallo Tourism
Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is SAR 648
SAR 735 total
includes taxes & fees
12 Jan - 13 Jan
Il Poggio dell'Eremita
Property grounds
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is SAR 20,774
SAR 22,956 total
includes taxes & fees
8 Feb - 9 Feb
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Pool
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is SAR 26,113
SAR 26,113 total
includes taxes & fees
8 Feb - 9 Feb
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Outdoor spa tub
Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Toscana
10.0 out of 10, Exceptional, (1 review)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
United States
Leopard I.
The price is SAR 8,641
SAR 9,872 total
includes taxes & fees
10 Feb - 11 Feb
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Pool
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

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, (1 review)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
Poland
Anonymous traveler
The price is SAR 7,664
SAR 10,451 total
includes taxes & fees
9 Feb - 10 Feb
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Outdoor dining
Tuscany Garden Villa

Tuscany Garden Villa

Tuscany Garden Villa
Figline Valdarno
10.0 out of 10, Exceptional, (2 reviews)
"Rymligt hus med bra toaletter! Väl utrustat kök. Saknade dock ac i ett av sovrummen"
Sweden
Gertrud R.
The price is SAR 1,527
SAR 2,195 total
includes taxes & fees
18 Jan - 19 Jan
Tuscany Garden Villa
Outdoor dining
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

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

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (3 reviews)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
United States
Lidija M.
The price is SAR 1,517
SAR 1,949 total
includes taxes & fees
11 Jan - 12 Jan
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Property grounds
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Rignano sull'Arno
7.0 out of 10, Good, (2 reviews)
"We arrived after dark, tired from long overnight flight. We had no water pressure upstairs and no hot water anywhere. This was corrected the next day. One on-suite toilette would not flush properly and leaked at the grinder motor. A "tech" was called in. He informed us that he could not fix it, they would need to call someone else. When we continued to report the issue to the host, she informed us that the "tech" said it was working OK. The "tech" informed us that it was not but he could not fix...
United States
Norman C.
The price is SAR 10,117
SAR 12,529 total
includes taxes & fees
12 Jan - 13 Jan
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Exterior
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is SAR 51,498
SAR 51,498 total
includes taxes & fees
9 Feb - 10 Feb
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Exterior
Villa w/ personal concierge service, heated pool only 20 min to Florence center

Villa w/ personal concierge service, heated pool only 20 min to Florence center

Villa w/ personal concierge service, heated pool only 20 min to Florence center
impruneta
10.0 out of 10, Exceptional, (106 reviews)
"The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property."
United States
Charles S.
The price is SAR 3,636
SAR 4,173 total
includes taxes & fees
22 Jan - 23 Jan
Villa w/ personal concierge service, heated pool only 20 min to Florence center
Exterior
Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (6 reviews)
"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"
United States
Frank V.
The price is SAR 2,828
SAR 5,224 total
includes taxes & fees
11 Jan - 12 Jan
Beautiful Tuscan home between Florence & Siena
Exterior
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning
Siena
The price is SAR 1,257
SAR 1,266 total
includes taxes & fees
8 Feb - 9 Feb
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning
Exterior
Villa "Il Fornacino" with Pool, Garden & Wi-Fi

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 SAR 2,725
SAR 3,807 total
includes taxes & fees
11 Jan - 12 Jan
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Pool
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is SAR 20,514
SAR 22,696 total
includes taxes & fees
11 Jan - 12 Jan
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Exterior
VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18

VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18

VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18
Cortona
10.0 out of 10, Exceptional, (1 review)
"The villa was simply awesome and perfect for our family holiday."
United Kingdom
Caroline H.
VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18
Exterior
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Montespertoli
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is SAR 5,586
SAR 6,398 total
includes taxes & fees
11 Jan - 12 Jan
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Exterior
Red Heart - relax with those you love in Tuscany.

Red Heart - relax with those you love in Tuscany.

Red Heart - relax with those you love in Tuscany.
Trequanda
The price is SAR 2,400
SAR 4,002 total
includes taxes & fees
11 Jan - 12 Jan
Red Heart - relax with those you love in Tuscany.
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

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

10/10 Excellent
"Very friendly staff. "
Teri 2-night trip
Posted 2 days ago
Radisson Blu Hotel, Florence

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between SAR 343 and SAR 28,149 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 1961 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.

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