Chianti Region Villas

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

1. Rooster House, cooking classes and opera

Toscana

HK$1,199 total

includes taxes & fees

17 Sept - 18 Sept

2. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

HK$4,160 total

includes taxes & fees

1 Sept - 2 Sept

3. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Impruneta

Maria H.

HK$3,225 total

includes taxes & fees

23 Aug - 24 Aug

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

Radda in Chianti

Amber M.

HK$9,313 total

includes taxes & fees

17 Sept - 18 Sept

5. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

Rignano sull'Arno

HK$3,955 total

includes taxes & fees

14 Sept - 15 Sept

6. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

Toscana

HK$8,146 total

includes taxes & fees

27 Aug - 28 Aug

1 bedroom, in-room safe, iron/ironing board, WiFi

7. My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

Rignano sull'Arno

HK$4,874 total

includes taxes & fees

17 Sept - 18 Sept

8. Villa with Pool - Two Bedrooms

Rignano sull'Arno (Florence)

HK$2,300 total

includes taxes & fees

20 Sept - 21 Sept

9. Villa Bellavista - Homelike Villas

Montegonzi

10. Podere Le Casette - Five Bedroom Villa, Sleeps 10

Cassia

Geoff B.

11. Villa with Pool - 3 Bedrooms with independent bathroom

Rignano sull'Arno

HK$3,796 total

includes taxes & fees

20 Sept - 21 Sept

12. Exclusive Estate | Heated Pool & Personal Concierge

impruneta

Charles S.

HK$12,140 total

includes taxes & fees

28 Aug - 29 Aug

13. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Gaiole in Chianti

Bernard K.

HK$10,117 total

includes taxes & fees

24 Aug - 25 Aug

14. My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

Rignano sull'Arno

HK$7,180 total

includes taxes & fees

20 Sept - 21 Sept

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

Montespertoli

Scott M.

HK$19,812 total

includes taxes & fees

1 Sept - 2 Sept

16. The San Leonino House

Castellina in Chianti

HK$12,128 total

includes taxes & fees

23 Aug - 24 Aug

17. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Vico dʼArbia

Marina O.

HK$11,823 total

includes taxes & fees

24 Aug - 25 Aug

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

Certaldo - Firenze

Kelly C.

HK$5,442 total

includes taxes & fees

23 Aug - 24 Aug

19. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Gaiole in Chianti

"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"

Anonymous traveller

HK$10,503 total

includes taxes & fees

30 Aug - 31 Aug

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.

HK$28,757 total

includes taxes & fees

1 Sept - 2 Sept

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Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

8/10 Good

"We had mixed feelings about our stay. The property and vineyard are beautiful, with fantastic Tuscan views. Our villa was spacious and private, the AC worked extremely well, and the semi-private pool was great with a small child. We booked through Expedia expecting more of a hotel/resort experience, but the villas operate as self-catering rentals. There was no daily housekeeping, fresh towels/linens, or replenishment of basics. We received three coffee pods and were directed to nearby grocery stores for additional provisions, so plan to stock up after arrival. We were surprised that villa guests could not use the main castle pool and were largely separate from the hotel areas. The four villas are in their own chain-link-fenced compound, which felt secluded from the otherwise beautiful property. Cleanliness could have been better: we found quite a bit of hair on arrival, and the shower flooded the bathroom with each use. We chose not to raise this during our stay. The pool itself is gorgeous, but the surrounding area felt unfinished, with loungers on gravel or long grass/weeds, few tables, and limited shade when multiple families were there. Overall, the villa has a lot going for it. Just arrive expecting a self-catering villa rather than the services and amenities of the hotel."

Villa Casagrande Resort & SPA

10/10 Excellent

"A beautiful hotel in a lovely little town. The staff were amazing, so helpful. The rooms were very clean and comfortable. I didn’t use the indoor pool or spa facilities so can’t comment on them. The outdoor pool is across the road and up a steep hill, so great if you have a car but not so much if you are on foot! Overall a very good stay."

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews	137
Accommodation	547 Villas
Lowest Price	HK$1,199
Highest Price	HK$28,757

Frequently asked questions

How much do villas in Chianti Region cost?

Villas in Chianti Region cost between HK$1,199 and HK$28,757 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 547 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 holiday 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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Chianti Region Holiday Rentals

Things to do in Poggibonsi

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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 Il Signorino

3. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

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

5. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

6. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

7. My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

8. Villa with Pool - Two Bedrooms

9. Villa Bellavista - Homelike Villas

10. Podere Le Casette - Five Bedroom Villa, Sleeps 10

11. Villa with Pool - 3 Bedrooms with independent bathroom

12. Exclusive Estate | Heated Pool & Personal Concierge

13. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

14. My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

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

16. The San Leonino House

17. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

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

19. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

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

Find holiday rentals that suit your style

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Find out more about Chianti Region

Chianti Region Villas information

Frequently asked questions

Explore a world of travel with Expedia