Chianti Region Villas - Villas in Chianti Region NZ$233

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

includes taxes & fees

15 Nov - 16 Nov

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

includes taxes & fees

15 Nov - 16 Nov

A table set for dining with wine glasses, a candle, and a view of a garden.

3. Villa with Pool - Two Bedrooms

Rignano sull'Arno (Florence)

includes taxes & fees

15 Nov - 16 Nov

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

4. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

impruneta

Oli P.

includes taxes & fees

18 Nov - 19 Nov

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

5. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

includes taxes & fees

15 Nov - 16 Nov

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

includes taxes & fees

15 Nov - 16 Nov

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

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

Montespertoli

includes taxes & fees

15 Nov - 16 Nov

A rectangular swimming pool with lounge chairs and a pergola, surrounded by a landscaped garden and a mountain backdrop.

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

Rignano sull'Arno

includes taxes & fees

15 Nov - 16 Nov

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

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

Vaggio

includes taxes & fees

23 Nov - 24 Nov

10. Villa in historic residence with swimming pool near Florence and Chianti

Figline Valdarno

includes taxes & fees

18 Nov - 19 Nov

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

11. 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.

includes taxes & fees

16 Nov - 17 Nov

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

12. Villa Torre Among the Hills of Siena

Vico dʼArbia

includes taxes & fees

15 Nov - 16 Nov

A rectangular swimming pool with a view of mountains and a clear sky.

13. VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

Firenze

includes taxes & fees

15 Nov - 16 Nov

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

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

Montespertoli

Krista G.

includes taxes & fees

29 Nov - 30 Nov

A stone building with a tiled roof, surrounded by a well-maintained lawn and trees.

15. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

includes taxes & fees

15 Nov - 16 Nov

An outdoor patio with a stone wall, a wooden bench, a cushioned sofa, and umbrellas providing shade.

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

Gaiole in Chianti

Bernard K.

includes taxes & fees

15 Nov - 16 Nov

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

17. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

includes taxes & fees

29 Nov - 30 Nov

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

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

Montespertoli

Scott M.

includes taxes & fees

15 Nov - 16 Nov

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

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

Certaldo - Firenze

Kelly C.

includes taxes & fees

15 Nov - 16 Nov

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

20. 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.

includes taxes & fees

15 Nov - 16 Nov

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Top Chianti Region Hotel Reviews

Salvadonica - Borgo del Chianti

10/10 Excellent

"Excelente servicio."

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 Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews	175
Accommodation	469 Villas
Lowest Price	NZ$233
Highest Price	NZ$28,221

Frequently asked questions

How much do villas in Chianti Region cost?

Villas in Chianti Region cost between NZ$233 and NZ$28,221 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 469 villas to choose from. Enter your destination and dates and lock in your perfect trip today.

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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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. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

5. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

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

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

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

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

10. Villa in historic residence with swimming pool near Florence and Chianti

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

12. Villa Torre Among the Hills of Siena

13. VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

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

15. Villa Capanna: A Window onto Tuscany

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

17. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

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

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

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

Find holiday rentals that suit your style

Top Chianti Region Hotel Reviews

Salvadonica - Borgo del Chianti

Find out more about Chianti Region

Chianti Region Villas information

Frequently asked questions

Explore a world of travel with Expedia