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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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 AU$269
includes taxes & fees
25 Sept - 26 Sept
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 AU$214
includes taxes & fees
24 Sept - 25 Sept
Rooster House, cooking classes and opera
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 AU$8,550
includes taxes & fees
28 Sept - 29 Sept
Villa "Arnilù" with Private Pool & Wi-Fi
A two-story building with a garden, a gazebo, and a statue.

4. 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 AU$5,848
includes taxes & fees
1 Oct - 2 Oct
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
The price is AU$11,293
includes taxes & fees
24 Sept - 25 Sept
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
A villa with a swimming pool, surrounded by lush greenery and hills.

6. Villa Linchiano with Historic Tower and Private Pool

Villa Linchiano with Historic Tower and Private Pool
Gambassi Terme
The price is AU$2,192
includes taxes & fees
24 Sept - 25 Sept
Villa Linchiano with Historic Tower and Private Pool
A swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

7. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is AU$8,893
includes taxes & fees
12 Oct - 13 Oct
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
An outdoor dining area with a table set for four, surrounded by brick pillars and white chairs.

8. 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
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

9. 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 AU$4,261
includes taxes & fees
18 Oct - 19 Oct
Villa Mami: A Tuscan Retreat of Elegance and Charm
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 AU$2,895
includes taxes & fees
4 Oct - 5 Oct
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A covered balcony with a brick railing, a bench, and a view of lush greenery.

11. 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 AU$939
includes taxes & fees
1 Oct - 2 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A swimming pool with lounge chairs and an umbrella, surrounded by green hills and a clear sky.

12. Ludovica and Marina Villas with 2 pools

Ludovica and Marina Villas with 2 pools
Lajatico
Ludovica and Marina Villas with 2 pools
A rural property with stone buildings, a garden, and a view of rolling hills.

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

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is AU$710
includes taxes & fees
30 Sept - 1 Oct
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
A brick building with a gravel courtyard, a staircase, and potted plants.

14. GuestHost - Porta Romana Elegant House with Private Parking!

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
The price is AU$567
includes taxes & fees
5 Oct - 6 Oct
GuestHost - Porta Romana Elegant House with Private Parking!
A person in a swimming pool with a view of a vineyard and hills.

15. "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 AU$2,760
includes taxes & fees
24 Sept - 25 Sept
"A Casa di Franca Villa con piscina"
A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

16. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is AU$8,789
includes taxes & fees
24 Sept - 25 Sept
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
A modern two-story house with a balcony, a well-maintained lawn, and potted plants.

17. 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 AU$2,403
includes taxes & fees
25 Sept - 26 Sept
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
A covered outdoor area with a pool, wicker furniture, and a view of the countryside.

18. 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 AU$4,281
includes taxes & fees
27 Sept - 28 Sept
Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

19. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is AU$2,758
includes taxes & fees
17 Oct - 18 Oct
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

20. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is AU$2,758
includes taxes & fees
17 Oct - 18 Oct
Villa Torre Among the Hills of Siena
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 Chiusarelli

Hotel Chiusarelli

8/10 Good
"This hotel is well maintained and delicious breakfast. Great location to walk to everything in Siena"
Christian 2-night trip
Posted 13 hours ago
Hotel Chiusarelli

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Number of reviews
12
Accommodation
1300 Villas
Lowest Price
AU$214
Highest Price
AU$11,293

Frequently asked questions

How much do villas in Casole dElsa cost?
Prices for villas in Casole dElsa range between AU$214 and AU$11,293 per night. No matter your budget, you'll find someplace that suits your needs with Expedia. This price was 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 dElsa?
Make use of your holiday days and choose from 1300 villas in Casole dElsa. For a family holiday, a getaway with friends and everything in between, Expedia will help you find the ideal place in just a click or two.
What is there to do near my villa in Casole dElsa?
Casole dElsa has enough activities and sights to keep you on the go for weeks (or months!), beginning with Sovestro in Poggio Winery. Museo Civico, Museum San Gimignano 1300 and Podestas Palace are other renowned attractions. If you're in town for longer, The Rock of Staggia and Colle di Val dElsa Cathedral are nice finishing touches to your itinerary.