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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Villas in Gaiole in Chianti

Pool
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

Villa in Gaiole in Chianti

The price is SAR 25,920
SAR 28,098 total
includes taxes & fees
1 Jan - 2 January 2026
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Terrace/patio
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

Villa in Gaiole in Chianti

10.0 out of 10, Exceptional, (7)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is SAR 2,399
SAR 2,504 total
includes taxes & fees
8 Dec - 9 Dec
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Exterior
Artisti del Cavallo Tourism

Villa in Foiano della Chiana

8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
The price is SAR 303
SAR 342 total
includes taxes & fees
11 Dec - 12 Dec
Artisti del Cavallo Tourism
Pool
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Villa in Siena

The price is SAR 26,065
SAR 26,065 total
includes taxes & fees
1 Jan - 2 January 2026
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Exterior
Il Poggio dell'Eremita

Villa in Sinalunga

10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is SAR 514
SAR 601 total
includes taxes & fees
5 Dec - 6 Dec
Il Poggio dell'Eremita
Exterior
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Villa in 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 SAR 5,456
SAR 6,233 total
includes taxes & fees
4 Dec - 5 Dec
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Exterior
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

Villa in Arezzo

10.0 out of 10, Exceptional, (18)
"Amazing location, great pool, ideal for a large group. Very friendly and helpful hosts. Second stay at this property would definitely consider it again. "
United Kingdom
Julie C.
The price is SAR 7,377
SAR 10,201 total
includes taxes & fees
7 Dec - 8 Dec
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
Pool
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa in 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 SAR 4,888
SAR 7,670 total
includes taxes & fees
5 Dec - 6 Dec
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Outdoor spa tub
Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villa in 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 SAR 7,778
SAR 8,887 total
includes taxes & fees
4 Dec - 5 Dec
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Exterior
Villa with concierge service & heated pool at 20 minute from Florence center

Villa in impruneta

10.0 out of 10, Exceptional, (105)
"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 5,260
SAR 6,024 total
includes taxes & fees
2 Jan - 3 January 2026
Villa with concierge service & heated pool at 20 minute from Florence center
Terrace/patio
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Villa in 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 SAR 1,498
SAR 1,939 total
includes taxes & fees
4 Dec - 5 Dec
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Outdoor dining
Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa in 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 SAR 2,125
SAR 3,205 total
includes taxes & fees
14 Dec - 15 Dec
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Property grounds
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Villa in 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 SAR 6,800
SAR 9,209 total
includes taxes & fees
4 Dec - 5 Dec
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Exterior
Villa Gabriella Chianti Toscana

Villa in Città Metropolitana di Firenze

6.0 out of 10, (1)
"le gestionnaire ne répond que très peu a nos courriels. C’est une superbe résidence qui manque malheureusement d’entretien. Des fourmis a l’entrée aux toiles d’araignées, mais surtout une forte odeur de moisissure qui embaume le 2eme étage au complet et même les draps et les matelas. Dans la cuisine: une forte odeur de créosote est présente dès que l’on ferme la porte. Le four au gas ne fonctionne pas. Le plafond coule. La piscine est superbe mais tous les coussins du mobilier extérieur sont...
Canada
Gilles C.
The price is SAR 1,207
SAR 2,601 total
includes taxes & fees
8 Dec - 9 Dec
Villa Gabriella Chianti Toscana
Outdoor pool
Beautiful Tuscan home between Florence & Siena

Villa in 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 SAR 3,143
SAR 5,587 total
includes taxes & fees
3 Jan - 4 January 2026
Beautiful Tuscan home between Florence & Siena
Exterior
Villa con Piscina, Sauna, Jacuzzi

Villa in Città Metropolitana di Firenze

6.0 out of 10, (2)
"Beautiful property, highly recommended. "
United States
Magdalena
The price is SAR 1,207
SAR 2,601 total
includes taxes & fees
8 Dec - 9 Dec
Villa con Piscina, Sauna, Jacuzzi
Exterior
Red Heart - relax with those you love in Tuscany.

Villa in Trequanda

The price is SAR 2,396
SAR 3,995 total
includes taxes & fees
4 Dec - 5 Dec
Red Heart - relax with those you love in Tuscany.
Exterior
Wonderful villa with private pool near Arezzo

Villa in Foiano della Chiana

The price is SAR 4,966
SAR 6,892 total
includes taxes & fees
3 Jan - 4 January 2026
Wonderful villa with private pool near Arezzo
Pool
Villa Bellavista - Homelike Villas

Villa in Montegonzi

Villa Bellavista - Homelike Villas
Pool
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

Villa in Tavarnelle Val di Pesa

The price is SAR 4,447
SAR 5,616 total
includes taxes & fees
9 Dec - 10 Dec
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
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

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"La habitación muy amplia, teníamos armario vestidor, sala, habitación amplia y un gran baño. Excelente la atención del personal. El lugar mágico maravilloso de epoca"
ROGERIO 5-night trip
Posted 3 days ago
Hotel Certosa Di Maggiano

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between SAR 342 and SAR 28,098 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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