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Our top choices for Gaiole in Chianti villas

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Gaiole in Chianti
The price is AED 25,590
AED 27,740 total
includes taxes & fees
23 Dec - 24 Dec
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

"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)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is AED 4,967
AED 5,071 total
includes taxes & fees
8 Jan - 9 January 2026
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
The price is AED 293
AED 331 total
includes taxes & fees
23 Dec - 24 Dec
Artisti del Cavallo Tourism

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is AED 25,733
AED 25,733 total
includes taxes & fees
23 Dec - 24 Dec
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is AED 638
AED 729 total
includes taxes & fees
23 Dec - 24 Dec
Il Poggio dell'Eremita

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)
"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 AED 6,923
AED 9,670 total
includes taxes & fees
25 Dec - 26 Dec
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is AED 20,216
AED 22,366 total
includes taxes & fees
1 Jan - 2 January 2026
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

Tuscany Garden Villa

Tuscany Garden Villa
Figline Valdarno
10.0 out of 10, Exceptional, (2)
"Rymligt hus med bra toaletter! Väl utrustat kök. Saknade dock ac i ett av sovrummen"
Sweden
Gertrud R.
The price is AED 1,505
AED 2,163 total
includes taxes & fees
16 Jan - 17 January 2026
Tuscany Garden Villa

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is AED 50,750
AED 50,750 total
includes taxes & fees
23 Dec - 24 Dec
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

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 AED 637
AED 645 total
includes taxes & fees
29 Dec - 30 Dec
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning

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)
"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 AED 1,476
AED 1,932 total
includes taxes & fees
23 Dec - 24 Dec
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

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)
"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 2,685
AED 3,752 total
includes taxes & fees
7 Jan - 8 January 2026
Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is AED 19,973
AED 21,568 total
includes taxes & fees
5 Jan - 6 January 2026
Villa "Arnilù" with Private Pool & Wi-Fi

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)
"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 AED 7,664
AED 8,666 total
includes taxes & fees
23 Dec - 24 Dec
Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (6)
"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 AED 3,097
AED 5,505 total
includes taxes & fees
3 Jan - 4 January 2026
Beautiful Tuscan home between Florence & Siena

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)
"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 AED 5,505
AED 6,305 total
includes taxes & fees
7 Jan - 8 January 2026
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18

VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18
Cortona
10.0 out of 10, Exceptional, (1)
"The villa was simply awesome and perfect for our family holiday."
United Kingdom
Caroline H.
The price is AED 3,071
AED 3,071 total
includes taxes & fees
7 Jan - 8 January 2026
VILLA LEOPOLDINA - Nine Bedroom Villa, Sleeps 18

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
United States
Ed M.
The price is AED 5,591
AED 6,404 total
includes taxes & fees
7 Jan - 8 January 2026
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

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)
"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 AED 8,325
AED 10,702 total
includes taxes & fees
23 Dec - 24 Dec
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Viniard Villa - Residence Le Rose in Chianti

Viniard Villa - Residence Le Rose in Chianti
Castellina in Chianti
The price is AED 1,376
AED 2,806 total
includes taxes & fees
26 Dec - 27 Dec
Viniard Villa - Residence Le Rose in Chianti
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

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between AED 331 and AED 27,740 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?
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