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

Chianti Region Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chianti Region vacation rentals

1. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (116 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is ₩145,474
₩163,339 total
includes taxes & fees
Sep 1 - Sep 2
Chianti Village Morrocco

2. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (255 reviews)
The price is ₩215,030
₩241,511 total
includes taxes & fees
Aug 30 - Aug 31
Relais Villa Olmo

3. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (168 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is ₩138,768
₩172,555 total
includes taxes & fees
Aug 3 - Aug 4
I Parigi Corbinelli

4. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ₩164,712
₩191,138 total
includes taxes & fees
Sep 1 - Sep 2
Villa San Filippo

5. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very Good, (94 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is ₩80,093
₩93,081 total
includes taxes & fees
Aug 30 - Aug 31
hu Firenze Certosa camping in town

6. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (37 reviews)
"Great spot"
Canada
Philippe
The price is ₩248,126
₩272,939 total
includes taxes & fees
Aug 10 - Aug 11
Villa di Sotto

7. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (102 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
The price is ₩384,598
₩429,695 total
includes taxes & fees
Aug 21 - Aug 22
Villa il Fedino

8. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is ₩263,659
₩303,298 total
includes taxes & fees
Aug 4 - Aug 5
Borgo Argenina

9. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is ₩185,045
₩206,867 total
includes taxes & fees
Sep 1 - Sep 2
Borgo di Erboli

10. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ₩176,471
₩200,762 total
includes taxes & fees
Aug 30 - Aug 31
Residenzia del Sogno

11. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is ₩452,052
₩503,894 total
includes taxes & fees
Aug 13 - Aug 14
Terre di Baccio

12. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (83 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ₩193,445
₩219,427 total
includes taxes & fees
Aug 3 - Aug 4
B&B La Fonte del Machiavelli

13. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (27 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is ₩165,141
₩188,292 total
includes taxes & fees
Aug 31 - Sep 1
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

14. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ₩164,010
₩183,729 total
includes taxes & fees
Sep 2 - Sep 3
Palazzo Pacini

15. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ₩339,369
₩376,617 total
includes taxes & fees
Aug 24 - Aug 25
Riserva di Fizzano Residence

16. Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (35 reviews)
"Estephano, the host, made us feel very welcome upon arrival. The room was spotless and fully equipped for a comfortable stay. There is also a small kitchen with everything you need if you want to cook. We wanted to go wine tasting, and Estephano kindly helped us book a wonderful experience. The property is conveniently located near bus stops, which made it easy to visit Florence without any issues, while still enjoying peaceful nights away from the hustle and bustle of the city. 🌿"
United States
Eduardo
The price is ₩102,913
₩118,182 total
includes taxes & fees
Aug 6 - Aug 7
Residence Il Connubio

17. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is ₩254,533
₩293,259 total
includes taxes & fees
Aug 9 - Aug 10
Villa Curina Resort

18. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is ₩131,830
₩151,650 total
includes taxes & fees
Aug 3 - Aug 4
Mariani Bed & Breakfast

19. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (328 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is ₩296,617
₩331,256 total
includes taxes & fees
Aug 20 - Aug 21
Hu Norcenni Girasole Village
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chianti Region Hotel Reviews

Find out more about Chianti Region

Search for Vacation rentals in Chianti Region on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chianti Region using one of the methods below:

  • View our selection of featured Vacation rentals in Chianti Region
  • Use the map to find apartments and other Vacation homes in the Chianti Region neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chianti Region while they last

Look no further and take a look at our great range of rental properties in Chianti Region!

Explore a world of travel with Expedia