Colle di Val d'Elsa Vacation Homes

A historic town with a prominent hilltop church and a bell tower.

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Our top choices for Colle di Val d'Elsa holiday homes

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

1. Casa Vacanze Le Case

San Gimignano

Andrew

HK$841 total

includes taxes & fees

2 Nov - 3 Nov

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

2. House with pool for 4 pax

Pievescola

Oliver E.

HK$2,433 total

includes taxes & fees

8 Oct - 9 Oct

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

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

casole d'elsa siena

Linda T.

HK$2,901 total

includes taxes & fees

9 Oct - 10 Oct

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

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

San Gimignano City Centre

HK$1,307 total

includes taxes & fees

5 Oct - 6 Oct

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

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$74,235 total

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.

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

San Gimignano City Centre

HK$1,811 total

includes taxes & fees

6 Oct - 7 Oct

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

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

San Gimignano

Anne-Marie M.

HK$3,811 total

includes taxes & fees

8 Oct - 9 Oct

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

8. 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

HK$4,195 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Radicondoli

HK$1,252 total

includes taxes & fees

3 Nov - 4 Nov

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

10. Your nest in the Tuscany countryside

Certaldo - Firenze

HK$2,023 total

includes taxes & fees

11 Oct - 12 Oct

A balcony with a table and chairs overlooking a vineyard.

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

San Gimignano

Bruno G.

HK$4,725 total

includes taxes & fees

5 Oct - 6 Oct

A stone building with a gravel path, outdoor seating, and greenery.

12. The Arch Among the Hills of Castellina

Topina

HK$2,411 total

includes taxes & fees

6 Oct - 7 Oct

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

13. 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

HK$1,402 total

includes taxes & fees

5 Oct - 6 Oct

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

14. Apartment in Chianti With Pool ID 513

Casole d'Elsa

HK$2,227 total

includes taxes & fees

5 Oct - 6 Oct

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

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

San Gimignano

Valerie S.

HK$4,911 total

includes taxes & fees

6 Oct - 7 Oct

A stone building with a central archway, multiple windows, and a paved courtyard with potted plants.

16. Farmhouse 'Le Volpaie - San Benedetto' with Shared Garden and Wi-Fi

San Gimignano

"The apartment, although a little rustic, suited most of our needs and the location was beautiful. Our host was very a helpful when we discovered there was no freezer to make ice cubes or freeze our ice pack overnight and she provided ice for us daily as well as freezing the ice pack each night. A wonderful host! A lovely relaxing place to wind down after a busy day touring Tuscany. I recommend this apartment."

Jacquie B.

HK$2,371 total

includes taxes & fees

5 Oct - 6 Oct

A compact living space with a kitchenette, a stone-patterned wall, a grey sofa, and a white radiator.

17. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Toscana

HK$1,554 total

includes taxes & fees

7 Oct - 8 Oct

A brick building with a garden, a metal fence, and a clear sky.

18. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,385 total

includes taxes & fees

13 Oct - 14 Oct

A modern hotel room with a walk-in closet, a vanity with a mirror, and a red accent wall.

19. Beautiful Superior Room, elegant and refined in the heart of San Gimignano.

San Gimignano City Centre

HK$1,917 total

includes taxes & fees

5 Oct - 6 Oct

A view through a wooden door of a courtyard with stone walls and potted plants.

20. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,616 total

includes taxes & fees

13 Oct - 14 Oct

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Top Colle di Val d'Elsa Hotel Reviews

Villa I Barronci Resort & Spa

8/10 Good

"We quite enjoyed the heated pool and views. Thank you for having us."

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."

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 Colle di Val d'Elsa