Title: Gaiole in Chianti Villas from CA $129 | Expedia.ca

[Gaiole in Chianti Travel Guide](https://expedia.ca/Gaiole-In-Chianti.dx603149)[Hotels in Gaiole in Chianti](https://expedia.ca/Gaiole-In-Chianti-Hotels.d603149.Travel-Guide-Hotels)[Vacation Rentals in Gaiole in Chianti](https://expedia.ca/Gaiole-In-Chianti-Vacation-Rentals.d603149.Travel-Guide-VacationRentals)[Flights to Gaiole in Chianti](https://expedia.ca/Cheap-Flights-To-Gaiole-In-Chianti.d603149.Travel-Guide-Flights)[Things to do in Gaiole in Chianti](https://expedia.ca/Things-To-Do-In-Gaiole-In-Chianti.d603149.Travel-Guide-Activities)[Gaiole in Chianti Car Rentals](https://expedia.ca/Car-Rentals-In-Gaiole-In-Chianti.d603149.Car-Rental-Guide)[Gaiole in Chianti Vacation Packages](https://expedia.ca/Gaiole-In-Chianti.d603149.Destination-Travel-Guides)

![View over the hills from the Brolio Castle](https://images.trvl-media.com/place/603149/c6d3b602-5ecb-46fa-8174-b38eecda296b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/603149/c6d3b602-5ecb-46fa-8174-b38eecda296b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=603149&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Gaiole in Chianti villas

![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/dcfa042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/25aedd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/afb73a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/52aa6660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information)

Gaiole in Chianti

CA $9,613

CA $10,421 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/8208f9d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/100f6cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/e04fd69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/4f173bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artisti del Cavallo Tourism

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

Foiano della Chiana

8.4/10

Very good

(24 reviews)

"Good house for one night. "

![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg)

Heiner

CA $114

CA $129 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/06c0aef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/8e90470c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/e78584cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/2598e840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

[](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.Hotel-Information)

Siena

CA $9,667

CA $9,667 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/c92c20b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/76c1c946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/aa63342e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/b48487ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information)

Colle Val D'Elsa

CA $19,065

CA $19,065 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d6476b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/ff9693c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d05582b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Il Poggio dell'Eremita

[](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information)

Sinalunga

10/10

Exceptional

(59 reviews)

"Fantastic place! Great location. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Paul Q.

CA $240

CA $275 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/w1920h1279x0y1-a132bf6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![9 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/0a5c24e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/bc5dd1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/09d64836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information)

Castellina in Chianti

CA $7,594

CA $8,402 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33320000/33313600/33313600/b93cd03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33320000/33313600/33313600/663d28a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33320000/33313600/33313600/24be0fb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33320000/33313600/33313600/289988b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

[](https://www.expedia.ca/Siena-Hotels-VILLA-ASCARA-Fifteen-Bedroom-Villa.h33313600.Hotel-Information)

Siena

CA $7,691

CA $8,498 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Siena-Hotels-VILLA-ASCARA-Fifteen-Bedroom-Villa.h33313600.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b8286297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b2bb8dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/03ae69bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/513cbcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information)

Radda in Chianti

10/10

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](https://a.travel-assets.com/egds/marks/flags/pl.svg)

Anonymous traveller

CA $2,837

CA $3,869 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/7f0bb06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/57059e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/7c521815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Spa](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/63f2ab21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information)

Toscana

10/10

Exceptional

(1 review)

"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leopard I.

CA $2,879

CA $3,290 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/38e5a789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h857x2y0-a94584e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h854x2y0-790f85bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/b0a52e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information)

Impruneta

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lidija M.

CA $562

CA $738 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/60af890d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/eabd8042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/a6e7b444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/f69f21a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information)

Rignano sull'Arno

7.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Norman C.

CA $3,745

CA $4,638 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/06053989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/682c69f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/37bf79c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/08415ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information)

Montespertoli

10/10

Exceptional

(38 reviews)

"Excellent in every way. Highly recommend"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed M.

CA $2,100

CA $2,399 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/122000000/121060000/121054000/121053909/06c9aff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121060000/121054000/121053909/w2033h1522x0y0-a990edd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121060000/121054000/121053909/9dea8d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121060000/121054000/121053909/f0ee7d44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Murlo-Hotels-Villa-La-Casa-Nel-Bosco-Antiche-Dimore-With-Shared-Pool.h121053909.Hotel-Information)

Siena

CA $465

CA $469 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Murlo-Hotels-Villa-La-Casa-Nel-Bosco-Antiche-Dimore-With-Shared-Pool.h121053909.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/0ac9183c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/24ff1535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/44cc70c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/bed5a9c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Rapolano-Terme-Hotels-Villa-Il-Fornacino-With-Pool.h89589245.Hotel-Information)

Rapolano Terme

9.0/10

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](https://a.travel-assets.com/egds/marks/flags/nl.svg)

Toon M.

CA $1,009

CA $1,409 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Rapolano-Terme-Hotels-Villa-Il-Fornacino-With-Pool.h89589245.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/bd7589fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/87d9fa0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/57f40b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/62d8efb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Tuscan home between Florence & Siena

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.Hotel-Information)

Florence

10/10

Exceptional

(7 reviews)

"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Frank V.

CA $1,440

CA $2,383 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/w2189h1640x4y5-0fbf58c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/51bd2610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/517571bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/87c073f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information)

Montespertoli

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elise D.

CA $2,068

CA $2,362 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/798e008d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/571a61ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/1b99bc10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/1b3afdb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Capanna: A Window onto Tuscany

[](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information)

Vico dʼArbia

CA $1,972

CA $2,132 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/7dec8a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/e3bba8c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/717cdd46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/2e9c5263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Torre Among the Hills of Siena

[](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information)

Vico dʼArbia

CA $1,972

CA $2,132 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/105000000/104130000/104120500/104120432/w2401h1080x4y0-f5dfa19a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/105000000/104130000/104120500/104120432/c525ee89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/105000000/104130000/104120500/104120432/11b713fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104130000/104120500/104120432/1e1ca09d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### VILLA IL MATTO with salt pool, with spa and sauna 

[](https://www.expedia.ca/Arezzo-Hotels-Vrbo-Property.h104120432.Hotel-Information)

Toscana

CA $292

CA $691 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Arezzo-Hotels-Vrbo-Property.h104120432.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/0dac13fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/ecc6720f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/876e46d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/6febdc0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Viniard Villa - Residence Le Rose in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Viniard-Villa-Residence-Le-Rose-In-Chianti.h123669271.Hotel-Information)

Castellina in Chianti

CA $517

CA $1,062 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Viniard-Villa-Residence-Le-Rose-In-Chianti.h123669271.Hotel-Information)

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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## Find vacation rentals that suit your style

Villas

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Private vacation homes

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Aparthotels

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Apartments

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Residences

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Cottages

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Condos

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Chalets

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## Top Gaiole in Chianti Hotel Reviews

![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/a501ded1_y.jpg)

### Hotel Chiusarelli

10/10 Excellent

"Perfect location … great quality/value … nice staff"

[](https://expedia.ca/Siena-Hotels-Hotel-Chiusarelli.h1110843.Hotel-Information)

![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg)

### Hotel Athena

10/10 Excellent

"Great hotel, beautiful view and excellent service from the personnel. "

[](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information)

![Grand Hotel Continental Siena – Starhotels Collezione](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b_y.jpg)

### Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Room, bathroom and breakfast were wonderful. WiFi was not great. Lovely location and pretty property. "

[](https://expedia.ca/Siena-Hotels-Grand-Hotel-Continental-Siena-Starhotels-Collezione.h796662.Hotel-Information)

![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/9acb6317_y.jpg)

###  Palazzo Ravizza

10/10 Excellent

"Excellent location, very clear instructions to get into the city for those coming in by car, a warm welcome by the staff, a super comfy bed and a great breakfast, what more could we ask for! All in all a great stay at the Palazzo."

[](https://expedia.ca/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.Hotel-Information)

![Radisson Blu Hotel, Florence](https://images.trvl-media.com/lodging/1000000/20000/14500/14476/91a79091_y.jpg)

### Radisson Blu Hotel, Florence

10/10 Excellent

"Lovely brand new hotel couldn’t fault a thing - easy to get to from the main motorways arrived very late Friday early hours sat morning the chap on reception was super nice and very friendly . Swimming pool outside will be lovely in the summer to cold in January . Recommend this hotel ."

[](https://expedia.ca/Florence-Hotels-Conference-Florentia-Hotel.h14476.Hotel-Information)

![Villa Olmi Firenze](https://images.trvl-media.com/lodging/2000000/1450000/1441600/1441538/09965ee7_y.jpg)

### Villa Olmi Firenze

10/10 Excellent

"Very charming, clean and fresh"

[](https://expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Olmi-Firenze.h1441538.Hotel-Information)

![Italiana Hotels Florence](https://images.trvl-media.com/lodging/1000000/10000/7700/7698/ab697e78_y.jpg)

### Italiana Hotels Florence

10/10 Excellent

"Clean room with nice staffs on site and at the restaurant "

[](https://expedia.ca/Florence-Hotels-Italiana-Hotels-Florence.h7698.Hotel-Information)

![La Certosa di Pontignano](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/11eaf7f7_y.jpg)

### La Certosa di Pontignano

10/10 Excellent

"Remarkable historic monastery well maintained in an extraordinary location. Food: superb Tuscan cuisine."

[](https://expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information)

![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/7edddb53_y.jpg)

### Hotel Italia

10/10 Excellent

"Nice clean room. Close to train/bus station. Very good breakfast "

[](https://expedia.ca/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information)

## Find out more about Gaiole in Chianti

## Gaiole in Chianti Villas information

| Number of reviews | 118         |
| ----------------- | ----------- |
| Accommodation     | 1961 Villas |
| Lowest Price      | CA $129     |
| Highest Price     | CA $10,421  |

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