Chianti Region Villas from CA $195

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region villas

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

1. Rooster House, Cooking Classes, and Opera

Tavarnelle Val di Pesa

CA $195 total

includes taxes & fees

Nov 10 - Nov 11

An outdoor patio with a stone wall, a wooden table, chairs, and a large umbrella. There are potted plants with red flowers and tall trees in the background.

2. Villa with Pool - 3 Bedrooms, each with a private bathroom

Rignano sull'Arno

CA $470 total

includes taxes & fees

Nov 15 - Nov 16

An outdoor dining area with tables and chairs, surrounded by greenery and a view of trees and hills.

3. Villa with Pool - Two Bedrooms

Rignano sull'Arno (Florence)

CA $291 total

includes taxes & fees

Nov 10 - Nov 11

A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

4. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

CA $22,292 total

includes taxes & fees

Nov 10 - Nov 11

A stone building with a large arched entrance, potted plants, and outdoor seating.

5. Exclusive Estate | Personal Concierge & Heated Pool

impruneta

Oli P.

CA $2,021 total

includes taxes & fees

Nov 10 - Nov 11

A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

6. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

Vaggio

CA $1,632 total

includes taxes & fees

Nov 10 - Nov 11

A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

7. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Rignano sull'Arno

CA $7,790 total

includes taxes & fees

Nov 10 - Nov 11

A large estate with a swimming pool, tennis court, and multiple guest rooms.

8. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

CA $18,577 total

includes taxes & fees

Nov 29 - Nov 30

A villa with a swimming pool, surrounded by lush greenery and vineyards.

9. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Montespertoli

CA $8,508 total

includes taxes & fees

Nov 15 - Nov 16

A modern outdoor pool area with a stone structure, a covered seating area, and a view of distant mountains.

10. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

Vaggio

CA $962 total

includes taxes & fees

Nov 10 - Nov 11

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

11. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Gaiole in Chianti

Bernard K.

CA $2,447 total

includes taxes & fees

Nov 15 - Nov 16

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

12. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

CA $2,343 total

includes taxes & fees

Nov 10 - Nov 11

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

13. Villa Torre Among the Hills of Siena

Vico dʼArbia

CA $2,343 total

includes taxes & fees

Nov 10 - Nov 11

A stone building with a swimming pool, wooden deck, and a tall tree.

14. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti

"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...

JIm B.

CA $1,697 total

includes taxes & fees

Nov 11 - Nov 12

A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

15. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Montespertoli

Krista G.

CA $2,220 total

includes taxes & fees

Nov 29 - Nov 30

A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

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

Montespertoli

"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!"

Elise D.

CA $2,254 total

includes taxes & fees

Dec 9 - Dec 10

A building with a large entrance, potted plants, and a statue in the foreground.

17. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

Scott M.

CA $2,554 total

includes taxes & fees

Nov 11 - Nov 12

A covered balcony with a brick railing, a bench, and a view of lush greenery.

18. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Certaldo - Firenze

Kelly C.

CA $1,830 total

includes taxes & fees

Nov 10 - Nov 11

A garden with potted plants and a view of a green landscape.

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

Rignano sull'Arno

"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...

Norman C.

CA $3,174 total

includes taxes & fees

Nov 10 - Nov 11

A residential area with a swimming pool, stone walls, and a view of houses and hills.

20. Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning

Vaggio

CA $959 total

includes taxes & fees

Nov 10 - Nov 11

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Top Chianti Region Hotel Reviews

Il Borro - Relais & Châteaux

10/10 Excellent

"Excellent unique property with top notch service, attention and experiences. The food and staff at Osteria Il Borro were exceptional!"

Borgo Vescine

10/10 Excellent

"There are no words to describe our experience at this incredibly beautiful and wonderful charming several century old village resort in Chianti. It was everything you imagined Italy to be in wine country. Probably one of my favorite places I have ever stayed at, and I’ve stayed at hundreds of of places around the world. The staff was wonderful, the accommodations were just super cool. It was once a village dating back over 100+ years. It was truly remarkable that the owner discovered it and restored it, creating a truly wonderful experience and beautiful Tuscany. We definitely will stay here every time we go to Tuscany in the future. This is a must-stay place!"

hu Firenze Certosa camping in town

8/10 Good

"Great location, superior tent was really nice with the en-suite and balcony. Easy check in. Staff friendly and helpful. Downsides were no designated parking space for us despite not all tents being occupied. Also bread given out at dinner were not free despite us not asking for them and at €6 a bag it was not great value. The bread was pretty hard and tasteless! Regardless I would recommend a stay here in the heart of Tuscany and within half an hour bus ride into Florence ♥️🇮🇹"

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews	187
Accommodation	535 Villas
Lowest Price	CA $195
Highest Price	CA $22,292

Frequently asked questions

How much do villas in Chianti Region cost?

Villas in Chianti Region cost between CA $195 and CA $22,292 per night. These escapes offer the privacy of your own space at a price that doesn't break the bank. 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 Chianti Region?

Chianti Region has 535 villas to choose from. Enter your destination and dates and lock in your perfect trip today.

Why book your villa in Chianti Region with Expedia?

We think arranging a vacation should be a breeze, so if you're looking for villas at a great price, Expedia delivers. Keep costs down and choose an all-inclusive stay, or splurge on a plush villa to spoil the ones you love most. Our handy filters make it easy to find a property in Chianti Region that matches your needs.

How can I find cheap villas in Chianti Region?

With Expedia's user-friendly filter tool, scoring cheap villas in Chianti Region has never been easier. To find stays that won't break the bank, fine-tune your search by star rating, budget and amenities.

What is there to do near my villa in Chianti Region?

Whether you love food, shopping, history or sightseeing, Chianti Region offers something for everyone! The major city of San Gimignano boasts lots of things to do, including Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery, Historical Torture Museum and Ornithological Museum. If you're headed to Radda in Chianti, Castello di Albola, Castello di Radda Winery and Borgo di Vescine - Tenute di Castelvecchi shouldn't be missed.

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Search Chianti Region Villa Rentals from CA $195

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region villas

1. Rooster House, Cooking Classes, and Opera

2. Villa with Pool - 3 Bedrooms, each with a private bathroom

3. Villa with Pool - Two Bedrooms

4. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

5. Exclusive Estate | Personal Concierge & Heated Pool

6. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

7. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

8. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

9. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

10. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

11. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

12. Villa Capanna: A Window onto Tuscany

13. Villa Torre Among the Hills of Siena

14. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

15. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

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

17. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

18. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

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

20. Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning

Find vacation rentals that suit your style

Top Chianti Region Hotel Reviews

Il Borro - Relais & Châteaux

Find out more about Chianti Region

Chianti Region Villas information

Frequently asked questions

Explore a world of travel with Expedia