Casole d'Elsa Villas - Best Villa Casole d'Elsa 2026

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

includes taxes & fees

27 Sept - 28 Sept

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

2. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

includes taxes & fees

27 Sept - 28 Sept

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

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

San Gimignano

includes taxes & fees

28 Sept - 29 Sept

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

includes taxes & fees

1 Oct - 2 Oct

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

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

Certaldo

includes taxes & fees

12 Oct - 13 Oct

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

6. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

includes taxes & fees

26 Sept - 27 Sept

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

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

Radda in Chianti

Amber M.

includes taxes & fees

4 Oct - 5 Oct

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

Lajatico

Carl P.

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Top Casole d'Elsa Hotel Reviews

Hotel Athena

10/10 Excellent

"Excellent location with free. And easy parking. Great breakfast, extremely kind and helpful staff, small but adequate shower. Would definitely stay here in the future!!"

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Beautiful property close to San Gimignano historic center. Loved having option to have all meals here. Breakfast was way more expensive than other hotels so just had breakfast in town. But other meals were reasonably priced. If they would step up their game a bit (more pillows, seating in rooms, provide wine glasses and opener, cozy it up a bit with amenities), they could easily be a 4 star because the property itself is certainly 4 star."

Fattoria di Vegi

10/10 Excellent

"This is a newly renovated and opened property cared for by a wonderful family. Everything has been taken care of down to the last detail. The food is delicious, the rooms are well appointed and till we thoroughly enjoyed exploring the property and every interesting nook! There's lots to do including a ping pong table and a beautiful pool. My only regret was not staying longer"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"This resort was simply beautiful! We stayed in the grand room as there were 5 of us, and it was much bigger than I expected! Three bedrooms, 3 washrooms, huge living room - it was great! As we had 2 kids, we had to use the family pool, which was conveniently close to our room. No bar at the pool, but there was a QR code to order drinks and food. There were towels at the pool as well. The staff were very kind and helpful. We appreciated the welcome gift of wine, juice, and snacks too! The breakfast buffet was lovely with lots of variety of hot and cold items. Would highly recommend this resort."

Castelfalfi

10/10 Excellent

"Our stay was perfect. We were given an upgrade due to the fact that it was our honeymoon. The staff was very kind and they work hard at pampering all guests. Property and rooms are extremely clean. Not sure if we went at a good time but the hotel was not crowded at all. Easy access to spa and other amenities which are also super clean. Loved our stay here, definitely the best hotel stay we’ve had"

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Number of reviews	12
Accommodation	1572 Villas
Lowest Price	€135
Highest Price	€7,014

Frequently asked questions

How much do villas in Casole d'Elsa cost?

You can expect to pay between €135 and €7,014 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 holiday days and choose from 1572 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.

Room 1

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Our top choices for Casole d'Elsa villas

1. Villa Montecastello

2. Rooster House, cooking classes and opera

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

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

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

6. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

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

8. Villa Ludovica with private pool, Borgo del Silenzio

9. Villa Linchiano with Historic Tower and Private Pool

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

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

12. Ludovica and Marina Villas with 2 pools

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

14. "A Casa di Franca Villa con piscina"

15. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

16. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

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

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

19. Villa Capanna: A Window onto Tuscany

20. Villa Torre Among the Hills of Siena

Find holiday rentals that suit your style

Top Casole d'Elsa Hotel Reviews

Hotel Athena

Hotel Casolare Le Terre Rosse

Fattoria di Vegi

Hotel Chiusarelli

Poderi Arcangelo

Palazzo Ravizza

NH Siena

Borgo Scopeto Wine & Country Relais

Castelfalfi

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Frequently asked questions

Search Villas in Casole d'Elsa

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Casole d'Elsa villas

1. Villa Montecastello

2. Rooster House, cooking classes and opera

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

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

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

6. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

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

8. Villa Ludovica with private pool, Borgo del Silenzio

9. Villa Linchiano with Historic Tower and Private Pool

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

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

12. Ludovica and Marina Villas with 2 pools

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

14. "A Casa di Franca Villa con piscina"

15. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

16. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

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

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

19. Villa Capanna: A Window onto Tuscany

20. Villa Torre Among the Hills of Siena

Find holiday rentals that suit your style

Top Casole d'Elsa Hotel Reviews

Hotel Athena

Find out more about Casole d'Elsa

Casole d'Elsa Villas information

Frequently asked questions