Casole d'Elsa Holiday Houses

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

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Our top choices for Casole d'Elsa holiday homes

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

1. House with pool for 4 pax

Pievescola

Oliver E.

includes taxes & fees

3 Oct - 4 Oct

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

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

casole d'elsa siena

Linda T.

includes taxes & fees

9 Oct - 10 Oct

A glass on a wooden table with a pool and a building in the background.

3. Apartment in Chianti With Pool ID 513

Casole d'Elsa

includes taxes & fees

4 Oct - 5 Oct

A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

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

Casole d'Elsa

"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...

Anonymous traveller

includes taxes & fees

2 Nov - 3 Nov

A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

5. Apartment in Chianti With Pool ID 3939

Casole d'Elsa

includes taxes & fees

7 Oct - 8 Oct

A stone building with a tiled roof, surrounded by lush greenery and a wooden pergola.

6. Apartment in Chianti With Pool ID 450

Casole d'Elsa

includes taxes & fees

4 Oct - 5 Oct

A balcony with potted plants and a view of rolling hills and mountains.

7. A Nest with a View - A Romantic Retreat Within the City Walls

Radicondoli

includes taxes & fees

1 Nov - 2 Nov

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

8. Casa Vacanze Le Case

San Gimignano

Andrew

includes taxes & fees

2 Nov - 3 Nov

A stone building with outdoor seating and umbrellas, overlooking a scenic view.

9. Romantic Getaway with Views

Montecastelli Pisano

Anonymous traveller

A rustic villa with a garden, a pond, and a mountainous backdrop.

10. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

includes taxes & fees

8 Oct - 9 Oct

A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

11. Deluxe Room- A cozy and elegant room in the heart of San Gimignano.

San Gimignano City Centre

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

12. Cozy double room with bathroom in the historic center of San Gimignano.

San Gimignano City Centre

includes taxes & fees

5 Oct - 6 Oct

A room with a bed, a chair, and a staircase leading to an upper level.

13. Holiday Home 'La Casetta' with Private Terrace, Garden & Wi-Fi

Volterra

includes taxes & fees

4 Oct - 5 Oct

A stone building with a patio area, outdoor seating, and a fire pit.

14. Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi

Castelnuovo di Val di Cecina

"We had the best time in this beautiful place! The location is absolutely stunning — the garden, house, pool, and everything was perfect and very clean. Tamara is super friendly and kind; she even brought us fresh bread every morning and sold us her delicious honey! Her two dogs are also very sweet and added to the warm, welcoming vibe of the place. The space is very spacious and a truly beautiful corner of nature that you must see.Thank you again, Tamara, for everything!"

Lea B.

includes taxes & fees

13 Oct - 14 Oct

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

15. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

includes taxes & fees

5 Oct - 6 Oct

A balcony with a table and chairs overlooking a vineyard.

16. "Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning

San Gimignano

Bruno G.

includes taxes & fees

4 Oct - 5 Oct

A rustic building with a brick facade, a small arched window, and a door.

17. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Toscana

"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."

Shanti R.

includes taxes & fees

4 Oct - 5 Oct

A swimming pool with a hot tub, outdoor seating, and a view of a hillside house.

18. Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

San Gimignano

Valerie S.

includes taxes & fees

5 Oct - 6 Oct

A room with a large sliding glass door leading to a pool area with a view of rolling hills and a distant village.

19. Your nest in the Tuscany countryside

Certaldo - Firenze

includes taxes & fees

11 Oct - 12 Oct

A stone building with a covered outdoor seating area and a brick pathway.

20. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

San Gimignano

Anne-Marie M.

includes taxes & fees

8 Oct - 9 Oct

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Top Casole d'Elsa Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

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 Holiday Homes information

Number of reviews	138
Accommodation	1476 Holiday Homes
Lowest Price	NZ$182
Highest Price	NZ$16,868

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Activities in Val d'Elsa

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Casole d'Elsa holiday homes

1. House with pool for 4 pax

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

3. Apartment in Chianti With Pool ID 513

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

5. Apartment in Chianti With Pool ID 3939

6. Apartment in Chianti With Pool ID 450

7. A Nest with a View - A Romantic Retreat Within the City Walls

8. Casa Vacanze Le Case

9. Romantic Getaway with Views

10. Ebbio – Villa and Organic Farm in Monteriggioni

11. Deluxe Room- A cozy and elegant room in the heart of San Gimignano.

12. Cozy double room with bathroom in the historic center of San Gimignano.

13. Holiday Home 'La Casetta' with Private Terrace, Garden & Wi-Fi

14. Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi

15. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

16. "Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning

17. Cozy Tuscan-style apartment Suitable for families. Pets allowed

18. Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

19. Your nest in the Tuscany countryside

20. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

Find holiday rentals that suit your style

Top Casole d'Elsa Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Borgo Scopeto Wine & Country Relais

Poderi Arcangelo

Castiglion del Bosco, A Rosewood Hotel

Fattoria di Vegi

Castelfalfi

Hotel Athena

Hotel Casolare Le Terre Rosse

La Certosa di Pontignano

Find out more about Casole d'Elsa

Casole d'Elsa Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in Casole d'Elsa

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Casole d'Elsa holiday homes

1. House with pool for 4 pax

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

3. Apartment in Chianti With Pool ID 513

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

5. Apartment in Chianti With Pool ID 3939

6. Apartment in Chianti With Pool ID 450

7. A Nest with a View - A Romantic Retreat Within the City Walls

8. Casa Vacanze Le Case

9. Romantic Getaway with Views

10. Ebbio – Villa and Organic Farm in Monteriggioni

11. Deluxe Room- A cozy and elegant room in the heart of San Gimignano.

12. Cozy double room with bathroom in the historic center of San Gimignano.

13. Holiday Home 'La Casetta' with Private Terrace, Garden & Wi-Fi

14. Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi

15. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

16. "Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning

17. Cozy Tuscan-style apartment Suitable for families. Pets allowed

18. Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

19. Your nest in the Tuscany countryside

20. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

Find holiday 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 Holiday Homes information

Explore a world of travel with Expedia