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

Casole d'Elsa Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Casole d'Elsa vacation rentals

A stone building with a tiled roof, a brick pathway, and a small grassy area.

1. Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
The price is ₩257,320
₩286,031 total
includes taxes & fees
Oct 25 - Oct 26
Le Mascie Country House
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

2. Apartment in Chianti With Pool ID 452

Apartment in Chianti With Pool ID 452
Casole d'Elsa
The price is ₩529,638
₩585,580 total
includes taxes & fees
Oct 22 - Oct 23
Apartment in Chianti With Pool ID 452
A stone building with a wooden door and a table with a vase of flowers.

3. Apartment in Chianti With Pool ID 455

Apartment in Chianti With Pool ID 455
Casole d'Elsa
The price is ₩529,638
₩585,580 total
includes taxes & fees
Oct 22 - Oct 23
Apartment in Chianti With Pool ID 455
A stone bench with a rustic fire pit in a garden setting.

4. Apartment in Chianti With Pool ID 513

Apartment in Chianti With Pool ID 513
Casole d'Elsa
The price is ₩359,403
₩398,322 total
includes taxes & fees
Oct 26 - Oct 27
Apartment in Chianti With Pool ID 513
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

5. Apartment in Chianti With Pool ID 3939

Apartment in Chianti With Pool ID 3939
Casole d'Elsa
The price is ₩529,638
₩585,580 total
includes taxes & fees
Oct 26 - Oct 27
Apartment in Chianti With Pool ID 3939
A swimming pool with lounge chairs and orange umbrellas, surrounded by stone buildings and trees.

6. Apartment in Chianti With Pool ID 450

Apartment in Chianti With Pool ID 450
Casole d'Elsa
The price is ₩529,638
₩585,580 total
includes taxes & fees
Oct 25 - Oct 26
Apartment in Chianti With Pool ID 450
A stone building with a tiled roof, surrounded by lush greenery and a wooden pergola.

7. Country House a Casole d Elsa ID 451

Country House a Casole d Elsa ID 451
Casole d'Elsa
The price is ₩718,793
₩793,651 total
includes taxes & fees
Oct 22 - Oct 23
Country House a Casole d Elsa ID 451
A garden with a stone pathway, wooden benches, and various potted plants.

8. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (88 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ₩201,113
₩228,673 total
includes taxes & fees
Oct 25 - Oct 26
Antico Borgo il Cardino
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

9. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ₩198,626
₩221,467 total
includes taxes & fees
Oct 25 - Oct 26
Palazzo Pacini
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

10. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ₩82,650
₩110,282 total
includes taxes & fees
Nov 4 - Nov 5
Tuscasì Aparthotel
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

11. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is ₩166,401
₩190,490 total
includes taxes & fees
Oct 23 - Oct 24
Borgo Il Poggiaccio
A stone building with outdoor seating and a view of the countryside.

12. Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is ₩225,491
₩252,509 total
includes taxes & fees
Oct 22 - Oct 23
Antico Borgo Poggiarello
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

13. 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 ₩246,699
₩275,837 total
includes taxes & fees
Oct 25 - Oct 26
Villa Montecastello
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

14. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (222 reviews)
"The room was so unique and convenient for everything we wanted to do. Wish we could have spent more than one night!"
United States
Kellie
The price is ₩135,160
₩154,635 total
includes taxes & fees
Nov 15 - Nov 16
Il Battistero Siena - Residenza d'Epoca
A reception desk with the word "SPORTLAND" prominently displayed.

15. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is ₩59,237
₩68,140 total
includes taxes & fees
Oct 25 - Oct 26
Sportland
A narrow street with stone buildings, a tower, and an archway.

16. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is ₩140,176
₩161,642 total
includes taxes & fees
Nov 4 - Nov 5
Materia Rooms San Gimignano
A bakery display with pastries and a coffee station.

17. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (215 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is ₩97,907
₩113,657 total
includes taxes & fees
Nov 2 - Nov 3
B&B Il Corso
A table set with breakfast items on a balcony overlooking a historic town.

18. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (133 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
The price is ₩203,144
₩229,418 total
includes taxes & fees
Nov 4 - Nov 5
Residenza d'Epoca Palazzo Borghesi
An open wooden door leading to an outdoor patio with a table and chairs.

19. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is ₩121,547
₩178,395 total
includes taxes & fees
Nov 7 - Nov 8
Palazzo al Torrione 2
A view from a window overlooking a rural landscape with fields and a distant mountain range.

20. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (67 reviews)
"Francesco, our host, is so nice and welcoming. We had the beat stay and our room had the most fantastic view. Excellent breakfast, place was super clean and quiet. We highly recommend."
Canada
Caroline
The price is ₩217,432
₩246,624 total
includes taxes & fees
Nov 11 - Nov 12
B&B Palazzo Tortoli
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Casole d'Elsa Hotel Reviews

Il Chiostro del Carmine

Il Chiostro del Carmine

8/10 Good
"Air conditioning was not working well. The bathroom was beautiful but the shower was cycling between very hot to very cold"
Maurice 3-night trip
Posted 6 hours ago
Il Chiostro del Carmine

Find out more about Casole d'Elsa

Search for Vacation rentals in Casole d'Elsa on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Casole d'Elsa using one of the methods below:

  • View our selection of featured Vacation rentals in Casole d'Elsa
  • Use the map to find apartments and other Vacation homes in the Casole d'Elsa neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Casole d'Elsa while they last

Look no further and take a look at our great range of rental properties in Casole d'Elsa!

Frequently asked questions

Can I find vacation rentals in Casole d'Elsa?

Yes, there are vacation rentals in Casole d'Elsa near Terre di Vini, or you can choose a more secluded option if you want a relaxing stay. Casole d'Elsa is known for its spas.

What's the top vacation rental that Casole d'Elsa has to offer?

Borgo Argiano: Visitors like this Casole d'Elsa vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Casole d'Elsa?

Expedia has 36 vacation rentals for your stay in Casole d'Elsa.

What’s there to see and do in Casole d'Elsa?

Family-friendly attractions include Terre di Vini, whereas Val di Merse is a spot to enjoy the outdoors. Archeological and Collegiate Church Museum and Colle di Val d'Elsa Cathedral are a couple of places you'll find in the larger area.

What’s a vacation rental in Casole d'Elsa like?

Vacation rentals are private properties you can stay in for a long or short time in Casole d'Elsa. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for small groups.