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

Casole d'Elsa Vacation Rentals

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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
$171 nightly
The price is $190
Oct 26 - Oct 27
Total with taxes and fees
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
$399 nightly
The price is $441
Oct 23 - Oct 24
Total with taxes and fees
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
$399 nightly
The price is $441
Oct 23 - Oct 24
Total with taxes and fees
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
$271 nightly
The price is $300
Oct 27 - Oct 28
Total with taxes and fees
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
$399 nightly
The price is $441
Oct 23 - Oct 24
Total with taxes and fees
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
$399 nightly
The price is $441
Oct 25 - Oct 26
Total with taxes and fees
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
$542 nightly
The price is $598
Oct 23 - Oct 24
Total with taxes and fees
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)
"friendly staff, gorgeous property"
United States
Heidi
$127 nightly
The price is $146
Oct 25 - Oct 26
Total with taxes and fees
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
$150 nightly
The price is $167
Oct 25 - Oct 26
Total with taxes and fees
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
$73 nightly
The price is $83
Nov 20 - Nov 21
Total with taxes and fees
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
$139 nightly
The price is $158
Oct 24 - Oct 25
Total with taxes and fees
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
$158 nightly
The price is $177
Oct 24 - Oct 25
Total with taxes and fees
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
$177 nightly
The price is $198
Oct 24 - Oct 25
Total with taxes and fees
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
$112 nightly
The price is $128
Nov 9 - Nov 10
Total with taxes and fees
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
$45 nightly
The price is $51
Oct 25 - Oct 26
Total with taxes and fees
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
$106 nightly
The price is $122
Nov 3 - Nov 4
Total with taxes and fees
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, (216 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
$74 nightly
The price is $86
Nov 22 - Nov 23
Total with taxes and fees
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, (135 reviews)
"Very beautiful rooms and amazing location!"
United States
Margaret
$141 nightly
The price is $159
Nov 4 - Nov 5
Total with taxes and fees
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
$117 nightly
The price is $134
Nov 7 - Nov 8
Total with taxes and fees
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
$123 nightly
The price is $141
Nov 4 - Nov 5
Total with taxes and fees
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.
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Top Casole d'Elsa Hotel Reviews

Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"Absolutely lovely hotel. Best one we stayed at in Italy - in retrospect, we wish we booked to stay here a second night. The location is quiet and isolated so stars are visible at night, plenty of parking, and breakfast is worth the 20 EURS, best breakfast options we had during our stay. Highly recommend, 10/10."
Maya 1-night trip
Posted 7 hours ago
Hotel Casolare Le Terre Rosse

Find out more about Casole d'Elsa

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Casole d'Elsa vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Casole d'Elsa vacation 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 low season months. For more hustle and bustle, you may prefer to visit Casole d'Elsa in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $56 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

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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.