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

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 CA $241
CA $269 total
includes taxes & fees
Oct 30 - Oct 31
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 CA $174
CA $207 total
includes taxes & fees
Oct 23 - Oct 24
Rooster House, cooking classes and opera
A covered balcony with a brick railing, a bench, and a view of lush greenery.

3. 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 CA $728
CA $920 total
includes taxes & fees
Oct 23 - Oct 24
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A stone building with a swimming pool, wooden deck, and a tall tree.

4. 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 CA $1,594
CA $2,354 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is CA $10,285
CA $11,075 total
includes taxes & fees
Oct 23 - Oct 24
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A person in a swimming pool with a view of a vineyard and hills.

6. "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 traveller
The price is CA $1,637
CA $2,412 total
includes taxes & fees
Nov 15 - Nov 16
"A Casa di Franca Villa con piscina"
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

7. Villa Mami: A Tuscan retreat full of elegance and charm

Villa Mami: A Tuscan retreat full of elegance and charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is CA $3,158
CA $4,309 total
includes taxes & fees
Oct 23 - Oct 24
Villa Mami: A Tuscan retreat full of elegance and charm
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

8. 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 CA $2,684
CA $2,986 total
includes taxes & fees
Nov 4 - Nov 5
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A building with a large entrance, potted plants, and a statue in the foreground.

9. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is CA $2,558
CA $2,561 total
includes taxes & fees
Nov 4 - Nov 5
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

10. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $2,120
CA $2,469 total
includes taxes & fees
Oct 28 - Oct 29
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

11. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,120
CA $2,469 total
includes taxes & fees
Oct 28 - Oct 29
Villa Torre Among the Hills of Siena
A villa with a swimming pool, surrounded by lush greenery and vineyards.

12. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is CA $8,527
CA $8,533 total
includes taxes & fees
Oct 25 - Oct 26
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

13. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is CA $2,842
CA $2,880 total
includes taxes & fees
Nov 15 - Nov 16
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

14. 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 CA $2,605
CA $2,898 total
includes taxes & fees
Nov 4 - Nov 5
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
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.

15. 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 CA $497
CA $720 total
includes taxes & fees
Oct 22 - Oct 23
Villa Il Signorino
A courtyard with a building, potted plants, and a grassy area.

16. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
Toscana
The price is CA $3,158
CA $3,512 total
includes taxes & fees
Nov 4 - Nov 5
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is CA $1,532
CA $1,719 total
includes taxes & fees
Oct 26 - Oct 27
Exclusive Estate | Personal Concierge & Heated Pool
A rural property with stone buildings, a garden, and a view of rolling hills.

18. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is CA $3,790
CA $3,944 total
includes taxes & fees
Oct 23 - Oct 24
Villetta Brunelleschi: Privacy and Comfort on Two Levels
Pool

19. Villa Sunset, in the heart of Chianti area

Villa Sunset, in the heart of Chianti area
Greve in Chianti
8.0 out of 10, Very good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti area
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

20. Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~

Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (4 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 CA $446
CA $596 total
includes taxes & fees
Oct 22 - Oct 23
Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
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 Italia

Hotel Italia

10/10 Excellent
"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."
Kurt 1-night trip
Posted 10 hours ago
Hotel Italia

Find out more about Colle di Val d'Elsa

Colle di Val d'Elsa Villas information

Number of reviews
195
Accommodation
1651 Villas
Lowest Price
CA $207
Highest Price
CA $11,075