Title: Chianti Region Villas from CA $722 | Expedia.ca

[Chianti Region Travel Guide](https://expedia.ca/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.ca/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Vacation Rentals in Chianti Region](https://expedia.ca/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.ca/Chianti-Region.d603148.Destination-Travel-Guides)

![Chianti Region showing farmland](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Search Chianti Region Villa Rentals from CA $722

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## Check prices for these dates

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=603148&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)

## Our top choices for Chianti Region villas

![TV, table tennis](https://images.trvl-media.com/lodging/72000000/71120000/71110900/71110823/8e622784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71120000/71110900/71110823/b9ac0df9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/72000000/71120000/71110900/71110823/93bc22ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71120000/71110900/71110823/d89e5ffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Figline Valdarno

[](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Tuscany-Garden-Villa.h71110823.Hotel-Information)

10/10

Exceptional

(2)

"Rymligt hus med bra toaletter! Väl utrustat kök. Saknade dock ac i ett av sovrummen"

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

Gertrud R.

CA $565

CA $813 total

includes taxes & fees

Jan 16 - Jan 17, 2026

[](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Tuscany-Garden-Villa.h71110823.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/f2af4ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/61b3ffc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/41d8a81a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/34f96c14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Gaiole in Chianti

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information)

10/10

Exceptional

(8)

"Country location but easy access to a great local winery/restaurant and the town of Gaiole."

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

russ h.

CA $901

CA $940 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/6112d62c.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)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/df76d7aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/28509faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Gaiole in Chianti

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

CA $9,612

CA $10,420 total

includes taxes & fees

Dec 21 - Dec 22

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

![Pool](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/368811a0.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)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/c031f145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Castellina in Chianti

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

CA $517

CA $1,059 total

includes taxes & fees

Dec 25 - Dec 26

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

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h830x2y0-085ca741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h835x2y0-8d015ca6.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/w1168h860x1y0-67cae5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Impruneta

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

10/10

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

Lidija M.

CA $554

CA $722 total

includes taxes & fees

Dec 21 - Dec 22

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

![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/5d1ad91c.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)

![5 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/c44dc7fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/4a362287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Radda in Chianti

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

10/10

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

Anonymous traveller

CA $2,601

CA $3,632 total

includes taxes & fees

Dec 23 - Dec 24

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

![Pool](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/1e6c21a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/dd7d2145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/944b728f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![7 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/6703c11a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Montespertoli

[](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information)

10/10

Exceptional

(1)

"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"

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

Scott M.

CA $2,617

CA $2,620 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/1b75a533.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)

![Pool](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/413438c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![9 bedrooms, free WiFi](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/0639021d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Castellina in Chianti

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

CA $7,594

CA $8,401 total

includes taxes & fees

Jan 2 - Jan 3, 2026

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

![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/a34e800d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/c21fb006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/73cc2cee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool, sun loungers](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/65e72921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in impruneta

[](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information)

10/10

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

Charles S.

CA $1,382

CA $1,585 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/c9dc3be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/1f150e3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/4214b7a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Florence

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

10/10

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

Frank V.

CA $1,163

CA $2,065 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](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/123000000/122490000/122488700/122488659/4cf121c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/ceef78fc.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/123000000/122490000/122488700/122488659/19fa198c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Colle Val D'Elsa

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

CA $19,063

CA $19,063 total

includes taxes & fees

Dec 21 - Dec 22

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

![Exterior](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/0f542ede.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)

![9 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/3223a586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/ecc1fffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Montespertoli

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

10/10

Exceptional

(38)

"Excellent in every way. Highly recommend"

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

Ed M.

CA $2,100

CA $2,405 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](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/33000000/32590000/32584300/32584249/w2189h1640x4y5-0fbf58c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/9937dca3.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)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/495a2b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Montespertoli

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

10/10

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

Elise D.

CA $2,068

CA $2,368 total

includes taxes & fees

Jan 9 - Jan 10, 2026

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

![Pool](https://images.trvl-media.com/lodging/96000000/95200000/95197700/95197661/d3a746b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/96000000/95200000/95197700/95197661/01b1b741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/96000000/95200000/95197700/95197661/142cf746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95200000/95197700/95197661/4813476e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Montegonzi

[](https://www.expedia.ca/Cavriglia-Hotels-Villa-Bellavista-Homelike-Villas.h95197661.Hotel-Information)

[](https://www.expedia.ca/Cavriglia-Hotels-Villa-Bellavista-Homelike-Villas.h95197661.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)

![6 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/f89f6ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/5448a085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/b543a4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Rignano sull'Arno

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

7.0/10

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

Norman C.

CA $2,724

CA $3,617 total

includes taxes & fees

Dec 21 - Dec 22

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

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/7a221817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/27650484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/4793210d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/09f4ffea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Vico dʼArbia

[](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information)

CA $1,729

CA $1,889 total

includes taxes & fees

Jan 10 - Jan 11, 2026

[](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/5657bedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/3b5e29fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/24bd1fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/a5994ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Tavarnelle Val di Pesa

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Villa-Virgilio-Colline-Del-Chianti-With-Mountain-View.h114506575.Hotel-Information)

CA $1,826

CA $2,260 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Villa-Virgilio-Colline-Del-Chianti-With-Mountain-View.h114506575.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/ff90371f.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)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/19cb3d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/16633e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Vico dʼArbia

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

CA $2,193

CA $2,352 total

includes taxes & fees

Dec 21 - Dec 22

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

![Pool](https://images.trvl-media.com/lodging/47000000/46380000/46375200/46375179/b87feaa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/47000000/46380000/46375200/46375179/f950f464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/47000000/46380000/46375200/46375179/45952c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo](https://images.trvl-media.com/lodging/47000000/46380000/46375200/46375179/02826b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Greve in chianti

[](https://www.expedia.ca/Greve-In-Chianti-Hotels-Wedding-Villa-In-Chianti-Villa-La-Veronica.h46375179.Hotel-Information)

[](https://www.expedia.ca/Greve-In-Chianti-Hotels-Wedding-Villa-In-Chianti-Villa-La-Veronica.h46375179.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/5adc06ce.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)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/586134cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/d02fb280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Vico dʼArbia

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

CA $2,193

CA $2,352 total

includes taxes & fees

Dec 21 - Dec 22

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

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Residences

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Cottages

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy&regionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-23&d2=2026-03-23&lodging=CABIN)

Condos

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Chalets

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## Top Chianti Region Hotel Reviews

![Castello di Fonterutoli Wine Resort](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg)

### Castello di Fonterutoli Wine Resort

10/10 Excellent

"Very clean,staff was very kind and helpful. Looking forward to come back! 😊"

[](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information)

![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg)

### Hotel Borgo di Cortefreda Relais

10/10 Excellent

"The hotel and services exceeded my expectations."

[](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information)

![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg)

### Hotel Toscana Ambassador

10/10 Excellent

"We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, stay here with no hesitation. "

[](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information)

![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg)

### Salvadonica - Borgo del Chianti

10/10 Excellent

"Great staff, great room and amenities. Outstanding romantic Tuscany location. Going back again."

[](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information)

![Hotel Palazzo San Lorenzo & SPA](https://images.trvl-media.com/lodging/4000000/3480000/3475000/3474921/1af45070_y.jpg)

### Hotel Palazzo San Lorenzo & SPA

10/10 Excellent

"Beautiful hotel and spa. Excellent amenities and modern luxuries. "

[](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information)

![Villa Castiglione](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b_y.jpg)

### Villa Castiglione

10/10 Excellent

"Nice and cute place. Great price. "

[](https://expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information)

![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg)

### COMO Castello Del Nero

10/10 Excellent

"Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). "

[](https://expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information)

![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg)

### Il Borro - Relais & Châteaux

10/10 Excellent

"A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia"

[](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information)

![Park Hotel Chianti](https://images.trvl-media.com/lodging/2000000/1410000/1402100/1402089/9fa8e1be_y.jpg)

### Park Hotel Chianti

10/10 Excellent

"Lovely hotel in Chianti, staff were outstanding! "

[](https://expedia.ca/Barberino-Tavarnelle-Hotels-Park-Hotel-Chianti.h1402089.Hotel-Information)

## Find out more about Chianti Region

## Chianti Region Villas information

| Number of reviews | 139        |
| ----------------- | ---------- |
| Accommodation     | 571 Villas |
| Lowest Price      | CA $722    |
| Highest Price     | CA $10,420 |

## Frequently asked questions

### How much do villas in Chianti Region cost?

### How many villas are there in Chianti Region?

### Why book your villa in Chianti Region with Expedia?

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- [Vacation Homes in Siena ](https://www.expedia.ca/Siena-Private-Vacation-Homes.d9821-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Townhomes in Siena ](https://www.expedia.ca/Siena-Townhomes.d9821-aaTownhomes.Travel-Guide-Accommodation)
- [Villas in Siena ](https://www.expedia.ca/Siena-Villas.d9821-aaVillas.Travel-Guide-Accommodation)
- [Villas in Tavarnelle Val di Pesa ](https://www.expedia.ca/Tavarnelle-Val-Di-Pesa-Villas.d6023366-aaVillas.Travel-Guide-Accommodation)
- [Vertine Hotels ](https://www.expedia.ca/Vertine-Hotels.d632712480144572416.Travel-Guide-Hotels)
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- [Volpaia Hotels ](https://www.expedia.ca/Volpaia-Hotels.d3000403024.Travel-Guide-Hotels)

- [Flights to Castellina in Chianti ](https://www.expedia.ca/Cheap-Flights-To-Castellina-In-Chianti.d55534.Travel-Guide-Flights)
- [Flights to Gaiole in Chianti ](https://www.expedia.ca/Cheap-Flights-To-Gaiole-In-Chianti.d603149.Travel-Guide-Flights)
- [Flights to San Donato in Poggio ](https://www.expedia.ca/Cheap-Flights-To-San-Donato-In-Poggio.d6292835.Travel-Guide-Flights)
- [Flights from Castellina in Chianti ](https://www.expedia.ca/lp/flights/55534/flights-from-castellina-in-chianti)
- [Flights from Gaiole in Chianti ](https://www.expedia.ca/lp/flights/603149/flights-from-gaiole-in-chianti)

- [Buondonno Winery ](https://www.expedia.ca/Buondonno-Winery-Castellina-in-Chianti.d553248635823420151.Vacation-Attraction)
- [Casa Vinicola Luigi Cecchi ](https://www.expedia.ca/Casa-Vinicola-Luigi-Cecchi-Castellina-in-Chianti.d6103262.Vacation-Attraction)
- [Visit Castelnuovo dei Sabbioni ](https://www.expedia.ca/Castelnuovo-Dei-Sabbioni.dx602580)
- [Church of San Sigismondo ](https://www.expedia.ca/Church-Of-San-Sigismondo-Gaiole-in-Chianti.d6238140.Vacation-Attraction)
- [Visit Gaiole in Chianti ](https://www.expedia.ca/Gaiole-In-Chianti.dx603149)
- [Visit Greve in Chianti ](https://www.expedia.ca/Greve-In-Chianti.dx601773)
- [Visit Meleto ](https://www.expedia.ca/Meleto.dx6292517)
- [Visit Montefioralle ](https://www.expedia.ca/Montefioralle.dx3000404943)
- [Visit Panzano in Chianti ](https://www.expedia.ca/Panzano-In-Chianti.dx602564)
- [Visit Ponte Agli Stolli ](https://www.expedia.ca/Ponte-Agli-Stolli.dx6342228)
- [Visit Radda in Chianti ](https://www.expedia.ca/Radda-In-Chianti.dx601693)
- [Visit San Donato in Poggio ](https://www.expedia.ca/San-Donato-In-Poggio.dx6292835)
- [Visit Sicelle ](https://www.expedia.ca/Sicelle.dx6343024)
- [Visit Vertine ](https://www.expedia.ca/Vertine.dx632712480144572416)

- [Car rental Castellina in Chianti ](https://www.expedia.ca/Car-Rentals-In-Castellina-In-Chianti.d55534.Car-Rental-Guide)
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- [Car rental Panzano in Chianti ](https://www.expedia.ca/Car-Rentals-In-Panzano-In-Chianti.d602564.Car-Rental-Guide)
- [Car rental Radda in Chianti ](https://www.expedia.ca/Car-Rentals-In-Radda-In-Chianti.d601693.Car-Rental-Guide)

- [Things to do in Fonterutoli ](https://www.expedia.ca/Things-To-Do-In-Fonterutoli.d6342141.Travel-Guide-Activities)
- [Things to do in Gaiole in Chianti ](https://www.expedia.ca/Things-To-Do-In-Gaiole-In-Chianti.d603149.Travel-Guide-Activities)
- [Things to do in Greve in Chianti ](https://www.expedia.ca/Things-To-Do-In-Greve-In-Chianti.d601773.Travel-Guide-Activities)
- [Things to do in Lecchi in Chianti ](https://www.expedia.ca/Things-To-Do-In-Lecchi-In-Chianti.d553248635974650979.Travel-Guide-Activities)
- [Things to do in Panzano in Chianti ](https://www.expedia.ca/Things-To-Do-In-Panzano-In-Chianti.d602564.Travel-Guide-Activities)

- [Book Villas in Chianti Region on Expedia.it ](https://www.expedia.it/Regione-Del-Chianti-Ville.d603148-aaVille.Guida-Viaggi-Alloggi)