A narrow street with stone buildings, a 'Zona traffico limitato' sign, and people walking.

Search Radda in Chianti Villa Rentals from CA $210

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Radda in Chianti villas

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

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

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is CA $1,800
CA $2,571 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

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

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is CA $1,083
CA $1,121 total
includes taxes & fees
Oct 4 - Oct 5
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

3. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is CA $176
CA $210 total
includes taxes & fees
Oct 4 - Oct 5
Rooster House, cooking classes and opera
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

4. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is CA $230
CA $258 total
includes taxes & fees
Oct 6 - Oct 7
Villa Montecastello
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

5. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

6. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is CA $504
CA $721 total
includes taxes & fees
Oct 6 - Oct 7
Villa Il Signorino
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is CA $10,418
CA $11,217 total
includes taxes & fees
Oct 4 - Oct 5
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

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

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very good, (1 review)
"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!"
Italy
Anonymous traveller
The price is CA $1,534
CA $1,833 total
includes taxes & fees
Oct 7 - Oct 8
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

9. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $2,258
CA $2,613 total
includes taxes & fees
Nov 2 - Nov 3
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

10. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,258
CA $2,613 total
includes taxes & fees
Nov 2 - Nov 3
Villa Torre Among the Hills of Siena
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

11. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is CA $2,212
CA $2,218 total
includes taxes & fees
Oct 4 - Oct 5
Molino In Chianti - Villa with Private Pool
A modern kitchen with built-in appliances, a dining area with a glass table, and a decorative shelf with books and vases.

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

Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Vaggio
The price is CA $863
CA $868 total
includes taxes & fees
Nov 2 - Nov 3
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Pool

13. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
8.0 out of 10, Very good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

14. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is CA $3,199
CA $4,384 total
includes taxes & fees
Oct 18 - Oct 19
Villa Mami: A Tuscan Retreat of Elegance and Charm
A stone building with a large glass door, a wooden deck, and a stone wall.

15. Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is CA $7,899
CA $8,492 total
includes taxes & fees
Oct 7 - Oct 8
Villa "Arnilù" with Private Pool & Wi-Fi
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

16. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is CA $321
CA $529 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa in the Florentine hills
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is CA $1,543
CA $1,768 total
includes taxes & fees
Oct 26 - Oct 27
Exclusive Estate | Personal Concierge & Heated Pool
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

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is CA $737
CA $932 total
includes taxes & fees
Oct 4 - Oct 5
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A house with a covered patio, a lawn, and potted plants.

19. Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi

Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
Reggello
The price is CA $978
CA $1,084 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
A two-story building with a garden, a gazebo, and a statue.

20. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is CA $6,892
CA $6,897 total
includes taxes & fees
Oct 7 - Oct 8
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Radda in Chianti Hotel Reviews

Villa Neroli

Villa Neroli

10/10 Excellent
"Definitely will return. The staff was so helpful in communicating before our trip like offering to schedule car service and local events. We had a large group and we enjoyed the excellent breakfast to start our day!"
Roxane 3-night trip
Posted 2 hours ago
Villa Neroli

Find out more about Radda in Chianti

Radda in Chianti Villas information

Number of reviews
286
Accommodation
1663 Villas
Lowest Price
CA $210
Highest Price
CA $11,217

Frequently asked questions

How much do villas in Radda in Chianti cost?
Rates for villas in Radda in Chianti range between CA $210 and CA $11,217 per night. No matter your budget, you're sure to find a place that fits your needs on Expedia. 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 Radda in Chianti?
Radda in Chianti has 1663 villas to select from. Find a place that's right for you quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.
Why book your villa in Radda in Chianti with Expedia?
Reserving a villa in Radda in Chianti is as simple as clicking on your travel dates and picking a place that meets your needs. Seeking something affordable or upmarket, or a stay that also features WiFi and a hot tub? Use Expedia's search filters to narrow your results and find your dream fit.
How can I find cheap villas in Radda in Chianti?
The simplest way to track down cheap villas in Radda in Chianti is with Expedia's filter tool. Tailor your search results by amenities, budget and star rating to access awesome prices in just a few keystrokes.
What is there to do near my villa in Radda in Chianti?
The perfect travel accessory is a well-planned schedule. Castello di Albola is a terrific place to begin your exploration of Radda in Chianti.