Casole d'Elsa Villas ￥23,367

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

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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

Monteriggioni

Alvaro

￥29,778 total

includes taxes & fees

Oct 4 - Oct 5

A stone building with a large glass door, a wooden deck, and a stone wall.

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

San Gimignano

￥947,129 total

includes taxes & fees

Oct 5 - Oct 6

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

3. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

￥23,367 total

includes taxes & fees

Oct 3 - Oct 4

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

Gambassi Terme

￥769,170 total

includes taxes & fees

Oct 7 - Oct 8

A villa with a swimming pool, surrounded by lush greenery and hills.

5. Villa Belvedere with Private Pool and Volterra Views

Gambassi Terme

￥357,276 total

includes taxes & fees

Oct 13 - Oct 14

A swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

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

Certaldo

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

Ron M.

￥1,251,021 total

includes taxes & fees

Oct 2 - Oct 3

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

8. Villa Mami: A Tuscan Retreat of Elegance and Charm

Toscana

￥487,487 total

includes taxes & fees

Oct 18 - Oct 19

A covered balcony with a brick railing, a bench, and a view of lush greenery.

9. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Certaldo - Firenze

Kelly C.

￥103,979 total

includes taxes & fees

Oct 3 - Oct 4

A brick building with a gravel courtyard, a staircase, and potted plants.

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

Siena

Kathleen M.

￥54,745 total

includes taxes & fees

Oct 5 - Oct 6

A person in a swimming pool with a view of a vineyard and hills.

11. "A Casa di Franca Villa con piscina"

Gambassi Terme

"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...

Anonymous traveler

￥331,174 total

includes taxes & fees

Oct 20 - Oct 21

A rural property with stone buildings, a garden, and a view of rolling hills.

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

Montaione

￥78,720 total

includes taxes & fees

Oct 2 - Oct 3

A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

13. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

￥973,619 total

includes taxes & fees

Oct 3 - Oct 4

A stone building with a swimming pool, wooden deck, and a tall tree.

14. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti

Amber M.

￥285,900 total

includes taxes & fees

Nov 1 - Nov 2

A pool with a view of rolling hills and a distant tower.

15. Villa Tosca

Peccioli

A covered outdoor area with a pool, wicker furniture, and a view of the countryside.

16. Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning

Monteverdi Marittimo

￥474,201 total

includes taxes & fees

Oct 6 - Oct 7

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

17. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

￥305,548 total

includes taxes & fees

Oct 28 - Oct 29

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

18. Villa Torre Among the Hills of Siena

Vico dʼArbia

￥305,548 total

includes taxes & fees

Oct 17 - Oct 18

A stone exterior wall, a glass door entrance, and a brick pathway leading to a staircase.

19. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

Massa Marittima

￥84,940 total

includes taxes & fees

Oct 5 - Oct 6

A building with a large entrance, potted plants, and a statue in the foreground.

20. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

Scott M.

￥321,424 total

includes taxes & fees

Nov 1 - Nov 2

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Top Casole d'Elsa Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"From the moment we checked in, This place was a Gem. From the friendly and helpful staff to the beautiful grounds, we were so impressed. Its hard to put into words how wonderful this Hotel is. The food, and drinks were incredible. We also celebrated my wife's birthday at this resort and they did a very special dinner for us to enjoy. Along with Campaign and a personalized Birthday dessert. Special thanks to Noamie (hope i got that right). She was absolutely wonderful. I could go on forever about this Resort. So easy to explore the region while calling this a comfortable landing spot. Can't thank the team enough for a wonderful stay."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Number of reviews	13
Accommodation	1579 Villas
Lowest Price	￥23,367
Highest Price	￥1,251,021

Frequently asked questions

How much do villas in Casole d'Elsa cost?

You can expect to pay between ￥23,367 and ￥1,251,021 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 vacation days and choose from 1579 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.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Casole d'Elsa villas

1. Villa Montecastello

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

3. Rooster House, cooking classes and opera

4. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

5. Villa Belvedere with Private Pool and Volterra Views

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

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

8. Villa Mami: A Tuscan Retreat of Elegance and Charm

9. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

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

11. "A Casa di Franca Villa con piscina"

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

13. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

14. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

15. Villa Tosca

16. Villa Podere Cafaggio with Private Pool, Terrace, and Air Conditioning

17. Villa Capanna: A Window onto Tuscany

18. Villa Torre Among the Hills of Siena

19. Villa Duomo Mare – Entire House with Garden & Terrace, Walk to Center

20. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Find vacation rentals that suit your style

Top Casole d'Elsa Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Frequently asked questions

Explore a world of travel with Expedia