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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Casole d'Elsa holiday rentals

A dining area with a table set for four, a large window with an arched ceiling, and a view of the outdoors.

1. La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
casole d'elsa siena
10.0 out of 10, Exceptional, (43 reviews)
"We stayed in this beautiful clean, fully airconditioned apartment for 12 days, perfect location for trips to the surrounding area like Siena, Florence, Monteriggioni, Volterra & San Gimignano. The apartment is situated in a peaceful Agriturismo with lots of privacy and a great swimming pool. The owners are really hospitable and you feel welcome right away. Highly recommendable."
Netherlands
Linda T.
The price is £297
includes taxes & fees
9 Oct - 10 Oct
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
A statue in a garden with a pool and lounge chairs.

2. Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
Toscana
The price is £286
includes taxes & fees
30 Sept - 1 Oct
Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

3. House with pool for 4 pax

House with pool for 4 pax
Pievescola
9.4 out of 10, Exceptional, (3 reviews)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is £244
includes taxes & fees
1 Oct - 2 Oct
House with pool for 4 pax
A stone building with a tiled roof, a brick pathway, and a small grassy area.

4. 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 £161
includes taxes & fees
4 Oct - 5 Oct
Le Mascie Country House
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

5. Rondine c/o Le Mascie

Rondine c/o Le Mascie
Sovicille
The price is £190
includes taxes & fees
12 Oct - 13 Oct
Rondine c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

6. Batticoda c/o Le Mascie

Batticoda c/o Le Mascie
Sovicille
The price is £285
includes taxes & fees
12 Oct - 13 Oct
Batticoda c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

7. Cardellino c/o Le Mascie

Cardellino c/o Le Mascie
Sovicille
The price is £285
includes taxes & fees
4 Oct - 5 Oct
Cardellino c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

8. Apartment in Chianti with pool ID 453

Apartment in Chianti with pool ID 453
Sovicille
The price is £285
includes taxes & fees
6 Oct - 7 Oct
Apartment in Chianti with pool ID 453
A stone building with a wooden door, a table with a vase of flowers, and a view of the countryside.

9. Apartment in Chianti with pool ID 3939

Apartment in Chianti with pool ID 3939
Sovicille
The price is £285
includes taxes & fees
7 Oct - 8 Oct
Apartment in Chianti with pool ID 3939
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

10. Pettirosso c/o Le Mascie

Pettirosso c/o Le Mascie
Sovicille
The price is £379
includes taxes & fees
30 Sept - 1 Oct
Pettirosso c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

11. Capinera c/o Le Mascie

Capinera c/o Le Mascie
Sovicille
The price is £379
includes taxes & fees
30 Sept - 1 Oct
Capinera c/o Le Mascie
A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

12. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning
Casole d'Elsa
10.0 out of 10, Exceptional, (1 review)
"Pros: Das Haus ist liebevoll eingerichtet, hat zwei schöne Bäder und eine wunderbare schattige Terrasse, von der man ins Grüne schaut, tagsüber ab und zu die Schafe nebenan und abends die Wildschweine hören kann. Das Haus liegt sehr ruhig in einem abgeschiedenen Weiler. Es sind ausreichend Liegestühle vorhanden, um im Garten zu entspannen. Die Klimaanlage im Haus funktioniert bestens. Besonders hervorzuheben sind die sehr herzlichen und hilfsbereiten Vermieter, die auch in dem kleinen Ort wohnen...
Germany
Anonymous traveller
The price is £445
includes taxes & fees
12 Oct - 13 Oct
Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

13. Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4

Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4
Sovicille
The price is £285
includes taxes & fees
1 Oct - 2 Oct
Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4
A garden with a stone pathway, wooden benches, and various potted plants.

14. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (86 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is £119
includes taxes & fees
27 Oct - 28 Oct
Antico Borgo il Cardino
A narrow street with stone buildings, a tower, and an archway.

15. 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 £107
includes taxes & fees
6 Oct - 7 Oct
Materia Rooms San Gimignano
An open wooden door leading to an outdoor patio with a table and chairs.

16. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is £114
includes taxes & fees
1 Oct - 2 Oct
Palazzo al Torrione 2
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

17. 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 £158
includes taxes & fees
14 Oct - 15 Oct
Borgo Il Poggiaccio
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

18. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is £107
includes taxes & fees
30 Oct - 31 Oct
Palazzo Pacini
A stone building with outdoor seating and a view of the countryside.

19. 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 £137
includes taxes & fees
11 Oct - 12 Oct
Antico Borgo Poggiarello
A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

20. Nido con vista

Nido con vista
Radicondoli
The price is £141
includes taxes & fees
30 Sept - 1 Oct
Nido con vista
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 Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"Absolutely stunning property with amazing staff. Tons of wineries close by and touring thru San Gimignano was fascinating. Definitely 5/5."
Jodie 1-night trip
Posted 3 hours ago
Hotel Casolare Le Terre Rosse

Find out more about Casole d'Elsa

Everything you need to know about Casole d'Elsa holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Casole d'Elsa holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Casole d'Elsa holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Casole d'Elsa holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Casole d'Elsa. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Casole d'Elsa holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Casole d'Elsa holiday rentals we have selected for you start as low as £42 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Casole d'Elsa rentals

At Expedia, we put the best Casole d'Elsa holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Casole d'Elsa rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Casole d'Elsa holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Casole d'Elsa. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Casole d'Elsa?

Yes, there are holiday rentals in Casole d'Elsa close to Terre di Vini, or you can select a more secluded option if you're looking for a relaxing stay. Casole d'Elsa is known for its spas.

What are some of the best holiday rentals that Casole d'Elsa has to offer?

Borgo Argiano: This holiday home rental outside of Casole d'Elsa is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library.

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

Expedia has 36 holiday 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 wider area.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Casole d'Elsa. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.