A cobblestone street with historic buildings, a wooden chair, and potted plants.

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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 Casole d'Elsa 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 £151
includes taxes & fees
24 Oct - 25 Oct
Villa Montecastello
A large building surrounded by dense trees and a clear sky.

2. 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 £3,650
includes taxes & fees
15 Oct - 16 Oct
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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 £114
includes taxes & fees
13 Oct - 14 Oct
Rooster House, cooking classes and opera
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

4. 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 £2,277
includes taxes & fees
18 Oct - 19 Oct
Villa Mami: A Tuscan Retreat of Elegance and Charm
A covered balcony with a brick railing, a bench, and a view of lush greenery.

5. 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 £493
includes taxes & fees
12 Oct - 13 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A person in a swimming pool with a view of a vineyard and hills.

6. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Spain
Anonymous traveller
The price is £1,189
includes taxes & fees
11 Oct - 12 Oct
"A Casa di Franca Villa con piscina"
A stone building with a swimming pool, wooden deck, and a tall tree.

7. 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 £1,357
additional charges may apply
9 Nov - 10 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A building with a large entrance, potted plants, and a statue in the foreground.

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

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is £1,525
includes taxes & fees
2 Nov - 3 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A stone building with a tower, surrounded by trees and a garden.

9. 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 £1,011
includes taxes & fees
6 Nov - 7 Nov
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
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 £1,379
includes taxes & fees
5 Nov - 6 Nov
Villa Torre Among the Hills of Siena
A rural property with stone buildings, a garden, and a view of rolling hills.

11. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is £2,114
includes taxes & fees
11 Oct - 12 Oct
Villetta Brunelleschi: Privacy and Comfort on Two Levels
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

12. 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 £1,546
additional charges may apply
3 Nov - 4 Nov
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Dining

13. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
The price is £564
includes taxes & fees
15 Oct - 16 Oct
Villa Liberty in The Centre - No Ztl
A rectangular swimming pool with a stone border, surrounded by lush greenery and tall trees.

14. Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
Chianni
Villa 'Karla' with Private Pool, Wi-Fi and Air Conditioning
A villa with a swimming pool, surrounded by lush greenery and hills.

15. Villa "Cristina" with sea view, private pool and Wi-Fi

Villa "Cristina" with sea view, private pool and Wi-Fi
Riparbella
9.8 out of 10, Exceptional, (12 reviews)
"Pros: The property was clean, very well appointed and had everything we needed. Gian was friendly, very helpful and responded quickly to messages. We would love to come back."
United States
Anonymous traveller
The price is £831
includes taxes & fees
4 Nov - 5 Nov
Villa "Cristina" with sea view, private pool and Wi-Fi
A stone exterior wall, a glass door entrance, and a brick pathway leading to a staircase.

16. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
Massa Marittima
The price is £403
includes taxes & fees
13 Oct - 14 Oct
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
A house with a stone wall, a large tree, and a patio area with a bench and table.

17. Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is £1,127
includes taxes & fees
11 Oct - 12 Oct
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

18. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
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 Casole d'Elsa Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Beautiful hotel in the city center with free parking which can be difficult to find. The staff was terrific"
Mark 3-night trip
Posted 2 hours ago
Palazzo Ravizza

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Number of reviews
30
Accommodation
1549 Villas
Lowest Price
£114
Highest Price
£3,650

Frequently asked questions

How much do villas in Casole d'Elsa cost?
You can expect to pay between £114 and £3,650 per night for a villa in Casole d'Elsa. No matter your budget, an ideal stay is only 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 Casole d'Elsa?
Reclaim your holiday days and choose from 1549 villas in Casole d'Elsa. For a family escape, a weekend getaway and everything in between, Expedia will help you find the perfect place in a few simple clicks.
Why book your villa in Casole d'Elsa with Expedia?
Reserving a villa in Casole d'Elsa is as simple as deciding on your travel dates and choosing the option that meets your needs. Want something affordable or upmarket, or a stay that also features a pool? Use Expedia's search filters to narrow your results and find your perfect match.
How can I find cheap villas in Casole d'Elsa?
The quickest way to compare cheap villas in Casole d'Elsa is with Expedia's helpful filter tool. Refine your search by budget, star rating and amenities to land unbeatable deals in only a few clicks.
What is there to do near my villa in Casole d'Elsa?
The ultimate travel accessory is a well-planned to-do list. Archeological and Collegiate Church Museum is a great place to begin your exploration of Casole d'Elsa.