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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Cavallari villas

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

1. 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 €185
includes taxes & fees
10 Oct - 11 Oct
Villa Montecastello
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

2. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is €135
includes taxes & fees
10 Oct - 11 Oct
Rooster House, cooking classes and opera
A stone building with a swimming pool, wooden deck, and a tall tree.

3. 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 €1,603
includes taxes & fees
1 Nov - 2 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
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.

4. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
The price is €457
includes taxes & fees
10 Oct - 11 Oct
Villa Il Signorino
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

5. 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 €1,824
includes taxes & fees
3 Nov - 4 Nov
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

6. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
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 €7,014
includes taxes & fees
10 Oct - 11 Oct
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

7. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A stone building with a tower, surrounded by trees and a garden.

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

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is €1,195
includes taxes & fees
2 Nov - 3 Nov
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

9. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is €1,629
includes taxes & fees
2 Nov - 3 Nov
Villa Torre Among the Hills of Siena
A stone building with a large arched entrance, potted plants, and outdoor seating.

10. 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 €1,108
includes taxes & fees
19 Oct - 20 Oct
Exclusive Estate | Personal Concierge & Heated Pool
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

11. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (151 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 €339
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
A covered balcony with a brick railing, a bench, and a view of lush greenery.

12. 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 €583
includes taxes & fees
10 Oct - 11 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

13. 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 €2,698
includes taxes & fees
18 Oct - 19 Oct
Villa Mami: A Tuscan Retreat of Elegance and Charm
Terrace/patio

14. Villa Sunset, in the heart of Chianti area

Villa Sunset, in the heart of Chianti area
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 area
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

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is €1,964
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
An outdoor dining area with tables and chairs, surrounded by greenery and a view of trees and hills.

16. Villa with Pool - Two Bedrooms

Villa with Pool - Two Bedrooms
Rignano sull'Arno (Florence)
The price is €185
includes taxes & fees
9 Nov - 10 Nov
Villa with Pool - Two Bedrooms
A two-story building with a garden, a gazebo, and a statue.

17. 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 €4,312
includes taxes & fees
11 Oct - 12 Oct
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
A villa with a swimming pool, surrounded by lush greenery and vineyards.

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

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is €5,404
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
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.

19. Villa with Pool - 3 Bedrooms, Each with a Private Bathroom

Villa with Pool - 3 Bedrooms, Each with a Private Bathroom
Rignano sull'Arno
The price is €340
includes taxes & fees
8 Nov - 9 Nov
Villa with Pool - 3 Bedrooms, Each with a Private Bathroom
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.
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Top Cavallari Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"Lovely hotel in Siena. Well located for exploring on foot with the main Palazzo and the Duomo no more than 15 minutes away. Really enjoyed the rooftop patio!"
Hillaine 3-night trip
Posted 6 hours ago
Hotel Athena

Find out more about Cavallari

Cavallari Villas information

Number of reviews
329
Accommodation
1396 Villas
Lowest Price
€135
Highest Price
€7,014

Frequently asked questions

How much do villas in Cavallari cost?
You'll pay between €135 and €7,014 per night for a villa in Cavallari. No matter your budget, a fantastic escape is just clicks away 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 Cavallari?
Cavallari has 1396 villas to select from. Find a place that's right for you quickly and easily by selecting the "Villa" checkbox under the "Property type" tab in our handy filter tool.
Why book your villa in Cavallari with Expedia?
Booking a villa in Cavallari is as easy as working out your travel dates and selecting an option that checks your boxes. Searching for something luxurious or affordable, or a stay that also offers free WiFi? Use Expedia's search filters to narrow your results and find the perfect fit.
How can I find cheap villas in Cavallari?
A fantastic way to get cheap villas in Cavallari is with Expedia's handy filter tool. Tailor your search results by amenities, star rating and budget to nab awesome bargains in just a couple of clicks.

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