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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 $255
CA $285 total
includes taxes & fees
Oct 24 - Oct 25
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 $176
CA $209 total
includes taxes & fees
Oct 13 - Oct 14
Rooster House, cooking classes and opera
A two-story building with a stone entrance, a paved driveway, and a well-maintained garden.

3. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is CA $6,881
CA $6,886 total
includes taxes & fees
Oct 16 - Oct 17
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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 CA $736
CA $931 total
includes taxes & fees
Oct 12 - Oct 13
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A stone building with a swimming pool, wooden deck, and a tall tree.

5. 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 $1,612
CA $2,380 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

6. 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 CA $3,194
CA $4,377 total
includes taxes & fees
Oct 18 - Oct 19
Villa Mami: A Tuscan Retreat of Elegance and Charm
A person in a swimming pool with a view of a vineyard and hills.

7. "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 $1,558
CA $2,244 total
includes taxes & fees
Oct 12 - Oct 13
"A Casa di Franca Villa con piscina"
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 $2,715
CA $3,088 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A villa with a swimming pool, surrounded by lush greenery and vineyards.

9. 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 $8,623
CA $8,630 total
includes taxes & fees
Oct 14 - Oct 15
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A building with a large entrance, potted plants, and a statue in the foreground.

10. 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 $2,874
CA $2,878 total
includes taxes & fees
Nov 1 - Nov 2
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
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.

11. 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 $503
CA $722 total
includes taxes & fees
Oct 12 - Oct 13
Villa Il Signorino
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

12. 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 $2,635
CA $2,997 total
includes taxes & fees
Nov 1 - Nov 2
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
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 $2,874
CA $2,913 total
includes taxes & fees
Nov 3 - Nov 4
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A rural property with stone buildings, a garden, and a view of rolling hills.

14. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is CA $3,833
CA $3,989 total
includes taxes & fees
Oct 12 - Oct 13
Villetta Brunelleschi: Privacy and Comfort on Two Levels
A stone building with a large arched entrance, potted plants, and outdoor seating.

15. 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 $1,557
CA $1,785 total
includes taxes & fees
Oct 19 - Oct 20
Exclusive Estate | Personal Concierge & Heated Pool
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 $3,194
CA $3,631 total
includes taxes & fees
Nov 1 - Nov 2
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

17. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $2,144
CA $2,497 total
includes taxes & fees
Oct 17 - Oct 18
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

18. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,144
CA $2,497 total
includes taxes & fees
Oct 17 - Oct 18
Villa Torre Among the Hills of Siena
Dining

19. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
The price is CA $1,037
CA $1,037 total
includes taxes & fees
Oct 15 - Oct 16
Villa Liberty in The Centre - No Ztl
Terrace/patio

20. 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
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 Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"This was one of the greatest hotel experiences we’ve had. The property is top notch. The staff are amazing. We plan on coming back for sure. It it centrally located to great sights and wineries, everything seemed to be 20 to 30 minutes away."
Joseph 4-night trip
Posted 5 hours ago
Hotel Borgo San Luigi

Find out more about Colle di Val d'Elsa

Colle di Val d'Elsa Villas information

Number of reviews
190
Accommodation
1651 Villas
Lowest Price
CA $209
Highest Price
CA $8,630