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

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Casole d'Elsa villas

Villa, Air conditioning, Courtyard View | Exterior

1. Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 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
11 Aug - 12 Aug
Villa Montecastello
Exterior

2. Apartment in villa with A/C, WIFI, pool, TV, terrace, panoramic view, close to San Gimignano

Apartment in villa with A/C, WIFI, pool, TV, terrace, panoramic view, close to San Gimignano
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 €164
includes taxes & fees
21 Aug - 22 Aug
Apartment in villa with A/C, WIFI, pool, TV, terrace, panoramic view, close to San Gimignano
Property grounds

3. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is €135
includes taxes & fees
6 Sept - 7 Sept
Rooster House, cooking classes and opera
Exterior

4. Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is €818
includes taxes & fees
10 Aug - 11 Aug
Villa Marcolina
Terrace/patio

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 €627
includes taxes & fees
7 Sept - 8 Sept
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Outdoor dining

6. Villa Marina with private pool, Borgo del Silenzio

Villa Marina with private pool, Borgo del Silenzio
Lajatico
"L’hébergement est situé au milieu de champs, superbe vue pour admirer le lever et coucher du soleil! La route en cailloux pour y accéder, dommage. C’est parfait pour les gens qui recherchent le calme! Maison propre. La literie pourrait être améliorée; matelas un peu durs. La piscine parfaite avec les enfants! L’accueil de Ludovica est agréable, très à l’écoute de nos besoins! Nous avons passé une belle semaine de vacances!"
Switzerland
Loic
Villa Marina with private pool, Borgo del Silenzio
Property grounds

7. 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 €1,409
includes taxes & fees
6 Sept - 7 Sept
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Pool

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 €890
includes taxes & fees
24 Aug - 25 Aug
"A Casa di Franca Villa con piscina"
Exterior

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

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is €354
includes taxes & fees
28 Aug - 29 Aug
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Exterior

10. 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 €1,813
includes taxes & fees
19 Aug - 20 Aug
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
Property grounds

11. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Toscana
10.0 out of 10, Exceptional, (1 review)
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Pool

12. 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 €1,554
includes taxes & fees
1 Sept - 2 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior detail

13. Villa Duomo Mare – Entire Private Home with Garden and Terrace, Walk to Center

Villa Duomo Mare – Entire Private Home with Garden and Terrace, Walk to Center
Massa Marittima
The price is €510
includes taxes & fees
7 Sept - 8 Sept
Villa Duomo Mare – Entire Private Home with Garden and Terrace, Walk to Center
Seasonal outdoor pool, pool umbrellas, pool loungers

14. Villa Tosca

Villa Tosca
Peccioli
The price is €1,233
includes taxes & fees
23 Aug - 24 Aug
Villa Tosca
Exterior

15. Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Siena
The price is €362
includes taxes & fees
1 Sept - 2 Sept
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Exterior

16. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
Villa Torre Among the Hills of Siena
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is €5,310
includes taxes & fees
10 Aug - 11 Aug
Villa "Arnilù" with Private Pool & Wi-Fi
Exterior

18. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is €410
includes taxes & fees
25 Aug - 26 Aug
Villetta Brunelleschi: Privacy and Comfort on Two Levels
Exterior

19. 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 €2,342
includes taxes & fees
13 Aug - 14 Aug
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Property grounds

20. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, 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 €1,590
includes taxes & fees
13 Aug - 14 Aug
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
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
"Two things that really made our stay at the Palazzo Ravizza exceptional were the charming terrace with a view of the Tuscan countryside, and the included continental breakfast offered in the morning, including plenty of drip coffee! ☕️ Our room was also undeniably European, with a painted ceiling and rustic furniture. The AC was sufficient, considering the daytime high on our visit was 100°. Service from the staff was very helpful, and they even called a taxi for us. The shower was hot with strong water pressure. The architecture of the hotel had some historic charm as well, with leaded glass doors, black and white marble floors, and vaulted ceilings in the public spaces. But that terrace... 😍"
Chris 1-night trip
Posted 2 days ago
Palazzo Ravizza

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Number of reviews
22
Accommodation
1572 Villas
Lowest Price
€135
Highest Price
€5,310

Frequently asked questions

How much do villas in Casole d'Elsa cost?
You can expect to pay between €135 and €5,310 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 1572 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.