Colle di Val d'Elsa Vacation Home Rentals from CA $204: Search Top Private Vacation Homes for Rent

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 vacation homes

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

1. Casa Vacanze Le Case

San Gimignano

Andrew

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

2. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

CA $204 total

includes taxes & fees

Nov 16 - Nov 17

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

3. Comfortable double room with a bathroom in the historic center of San Gimignano.

San Gimignano City Centre

CA $222 total

includes taxes & fees

Nov 16 - Nov 17

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

4. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

CA $13,221 total

includes taxes & fees

Nov 17 - Nov 18

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

5. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

San Gimignano City Centre

CA $304 total

includes taxes & fees

Nov 16 - Nov 17

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

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

San Gimignano

Anne-Marie M.

CA $765 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Casole d'Elsa

Anonymous traveller

CA $701 total

includes taxes & fees

Nov 16 - Nov 17

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

8. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

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

CA $239 total

includes taxes & fees

Nov 16 - Nov 17

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

9. Apartment in Chianti With Pool ID 513

Casole d'Elsa

CA $421 total

includes taxes & fees

Nov 16 - Nov 17

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

10. Casa Marisa in Castellina in Chianti

Castellina in Chianti

CA $425 total

includes taxes & fees

Nov 16 - Nov 17

A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

11. Siena Love Nest: Romantic Suite with Spa & Jacuzzi

Toscana

CA $261 total

includes taxes & fees

Nov 16 - Nov 17

A balcony with a view of a stone building and surrounding landscape.

12. A Nest with a View - A Romantic Getaway Within the City Walls

Radicondoli

CA $255 total

includes taxes & fees

Nov 16 - Nov 17

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

13. A beautiful, elegant, and sophisticated superior room in the heart of San Gimignano.

San Gimignano City Centre

CA $324 total

includes taxes & fees

Nov 16 - Nov 17

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

14. Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano

San Gimignano

CA $527 total

includes taxes & fees

Dec 5 - Dec 6

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

15. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

CA $263 total

includes taxes & fees

Nov 17 - Nov 18

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

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

San Gimignano

Valerie S.

CA $931 total

includes taxes & fees

Nov 16 - Nov 17

A room with a view of a vineyard through an arched window, a bottle of wine, and a plate of fruit.

17. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

Tavarnelle Val di Pesa

CA $287 total

includes taxes & fees

Nov 16 - Nov 17

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

18. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

CA $510 total

includes taxes & fees

Nov 16 - Nov 17