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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Colle di Val d'Elsa villas

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

1. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is ￥26,853
￥30,080 total
includes taxes & fees
Sep 25 - Sep 26
Villa Montecastello
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

2. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is ￥19,819
￥23,603 total
includes taxes & fees
Oct 2 - Oct 3
Rooster House, cooking classes and opera
A stone building with a swimming pool, wooden deck, and a tall tree.

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

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is ￥87,013
￥173,656 total
includes taxes & fees
Sep 24 - Sep 25
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A covered balcony with a brick railing, a bench, and a view of lush greenery.

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

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is ￥83,058
￥105,032 total
includes taxes & fees
Oct 8 - Oct 9
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

5. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is ￥56,756
￥80,900 total
includes taxes & fees
Sep 23 - Sep 24
Villa Il Signorino
A rural property with stone buildings, a garden, and a view of rolling hills.

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

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is ￥41,266
￥58,941 total
includes taxes & fees
Sep 23 - Sep 24
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

7. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (3 reviews)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
The price is ￥50,846
￥67,963 total
includes taxes & fees
Sep 25 - Sep 26
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
A person in a swimming pool with a view of a vineyard and hills.

8. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"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...
Spain
Anonymous traveler
The price is ￥154,406
￥231,930 total
includes taxes & fees
Sep 23 - Sep 24
"A Casa di Franca Villa con piscina"
A brick building with a gravel courtyard, a staircase, and potted plants.

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

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
The price is ￥31,421
￥59,797 total
includes taxes & fees
Oct 5 - Oct 6
GuestHost - Porta Romana Elegant House with Private Parking!
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is ￥890,803
￥957,692 total
includes taxes & fees
Sep 28 - Sep 29
Villa "Arnilù" with Private Pool & Wi-Fi
A table set for tea with a view of a garden and hills.

11. Tuscan Sky Villa in San Miniato with Private Pool

Tuscan Sky Villa in San Miniato with Private Pool
San Miniato
The price is ￥67,539
￥119,790 total
includes taxes & fees
Sep 24 - Sep 25
Tuscan Sky Villa in San Miniato with Private Pool
A modern two-story house with a balcony, a well-maintained lawn, and potted plants.

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

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
San Vivaldo
The price is ￥210,677
￥268,875 total
includes taxes & fees
Sep 25 - Sep 26
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
An outdoor dining area with a table set for four, surrounded by brick pillars and white chairs.

13. Villa Ludovica with private pool, Borgo del Silenzio

Villa Ludovica with private pool, Borgo del Silenzio
Lajatico
10.0 out of 10, Exceptional, (1 review)
"Mooie villa met alle accommodatie op een unieke ligging"
Netherlands
Carl P.
Villa Ludovica with private pool, Borgo del Silenzio
A stone building with a tower, surrounded by trees and a garden.

14. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is ￥186,492
￥226,351 total
includes taxes & fees
Oct 17 - Oct 18
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

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

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is ￥360,720
￥488,054 total
includes taxes & fees
Oct 18 - Oct 19
Villa Mami: A Tuscan Retreat of Elegance and Charm
A courtyard with a paved area, potted plants, and a grassy lawn.

16. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is ￥297,594
￥339,798 total
includes taxes & fees
Sep 23 - Sep 24
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

17. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is ￥249,172
￥249,893 total
includes taxes & fees
Sep 24 - Sep 25
Molino In Chianti - Villa with Private Pool
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

18. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Montespertoli
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is ￥315,310
￥344,679 total
includes taxes & fees
Oct 12 - Oct 13
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
A swimming pool with lounge chairs and an umbrella, surrounded by green hills and a clear sky.

19. Ludovica and Marina Villas with 2 pools

Ludovica and Marina Villas with 2 pools
Lajatico
Ludovica and Marina Villas with 2 pools
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

20. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is ￥268,824
￥308,643 total
includes taxes & fees
Oct 18 - Oct 19
Villa Torre Among the Hills of Siena
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Colle di Val d'Elsa Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"This hotel is well maintained and delicious breakfast. Great location to walk to everything in Siena"
Christian 2-night trip
Posted 7 hours ago
Hotel Chiusarelli

Find out more about Colle di Val d'Elsa

Colle di Val d'Elsa Villas information

Number of reviews
73
Accommodation
1650 Villas
Lowest Price
￥23,603
Highest Price
￥957,692