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

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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 £148
includes taxes & fees
29 Aug - 30 Aug
Villa Montecastello
A stone building with a sloped roof, arched windows, and a small garden with flowers and shrubs.

2. Cosy apartment in villa with WIFI, pool, A/C, TV, terrace and panoramic view, close to San Gimig...

Cosy apartment in villa with WIFI, pool, A/C, TV, terrace and panoramic view, close to San Gimig...
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
The price is £141
includes taxes & fees
28 Aug - 29 Aug
Cosy apartment in villa with WIFI, pool, A/C, TV, terrace and panoramic view, close to San Gimig...
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is £4,545
includes taxes & fees
25 Aug - 26 Aug
Villa "Arnilù" with Private Pool & Wi-Fi
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

4. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is £115
includes taxes & fees
27 Aug - 28 Aug
Rooster House, cooking classes and opera
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is £4,145
includes taxes & fees
25 Aug - 26 Aug
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
A covered balcony with a brick railing, a bench, and a view of lush greenery.

6. 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 £508
includes taxes & fees
30 Aug - 31 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A modern two-story house with a balcony, a well-maintained lawn, and potted plants.

7. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
San Vivaldo
The price is £2,028
includes taxes & fees
30 Aug - 31 Aug
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
A person in a swimming pool with a view of a vineyard and hills.

8. "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 £1,124
includes taxes & fees
25 Aug - 26 Aug
"A Casa di Franca Villa con piscina"
A rural property with stone buildings, a garden, and a view of rolling hills.

9. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is £303
includes taxes & fees
28 Aug - 29 Aug
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
A stone building with a swimming pool, wooden deck, and a tall tree.

10. 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 £871
additional charges may apply
18 Sept - 19 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
An outdoor dining area with a table set for four, surrounded by brick pillars and white chairs.

11. Villa Ludovica with private pool, Borgo del Silenzio

Villa Ludovica with private pool, Borgo del Silenzio
Lajatico
10.0 out of 10, Exceptional, (1 review)
"Mooie villa met alle accommodatie op een unieke ligging"
Netherlands
Carl P.
Villa Ludovica with private pool, Borgo del Silenzio
A villa with a swimming pool, surrounded by lush greenery and hills.

12. Villa Linchiano with Historic Tower and Private Pool

Villa Linchiano with Historic Tower and Private Pool
Gambassi Terme
The price is £2,228
includes taxes & fees
19 Sept - 20 Sept
Villa Linchiano with Historic Tower and Private Pool
A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

13. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is £4,672
includes taxes & fees
25 Aug - 26 Aug
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
A pathway leading to a building with a brick base and a tiled upper section.

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

Villa Bonriposo with Private Pool, Wi-Fi, and Air Conditioning
Legoli
The price is £2,345
includes taxes & fees
14 Sept - 15 Sept
Villa Bonriposo with Private Pool, Wi-Fi, and Air Conditioning

15. 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 £476
includes taxes & fees
7 Sept - 8 Sept
Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center
A stone building with a tower, surrounded by trees and a garden.

16. 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 £1,104
includes taxes & fees
25 Aug - 26 Aug
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A building with a large entrance, potted plants, and a statue in the foreground.

17. 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 £1,850
includes taxes & fees
1 Sept - 2 Sept
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

18. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is £1,511
includes taxes & fees
30 Aug - 31 Aug
Villa Torre Among the Hills of Siena
A pool with a view of rolling hills and a distant tower.

19. Villa Tosca

Villa Tosca
Peccioli
The price is £1,055
includes taxes & fees
10 Sept - 11 Sept
Villa Tosca
A covered outdoor area with a pool, wicker furniture, and a view of the countryside.

20. Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning

Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
Monteverdi Marittimo
The price is £3,067
includes taxes & fees
5 Sept - 6 Sept
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
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

Hotel Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Fabulous family friendly property in Tuscany. Easy to get to many different towns. Staff were very helpful and lots of space!"
Sara 4-night trip
Posted 3 days ago
Hotel Borgo San Luigi

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Number of reviews
15
Accommodation
1549 Villas
Lowest Price
£115
Highest Price
£4,672

Frequently asked questions

How much do villas in Casole d'Elsa cost?
You can expect to pay between £115 and £4,672 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.