Colle di Val d'Elsa Villas

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 villas

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

1. Villa Montecastello

Monteriggioni

Alvaro

HK$1,682 total

includes taxes & fees

3 Sept - 4 Sept

A building with a yellow exterior, a door with a number 11 sign, and a window with a potted plant.

2. The three owls of san gimignano

San Gimignano

HK$991 total

includes taxes & fees

3 Sept - 4 Sept

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

3. Rooster House, cooking classes and opera

Toscana

HK$1,190 total

includes taxes & fees

1 Sept - 2 Sept

A stone building with a large glass door, a wooden deck, and a stone wall.

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

San Gimignano

HK$48,228 total

includes taxes & fees

31 Aug - 1 Sept

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

Gambassi Terme

HK$34,316 total

includes taxes & fees

30 Sept - 1 Oct

A stone building with a swimming pool, wooden deck, and a tall tree.

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

Radda in Chianti

Amber M.

HK$8,754 total

includes taxes & fees

17 Sept - 18 Sept

7. The San Leonino House

Castellina in Chianti

HK$12,021 total

includes taxes & fees

31 Aug - 1 Sept

A covered balcony with a brick railing, a bench, and a view of lush greenery.

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

Certaldo - Firenze

Kelly C.

HK$5,544 total

includes taxes & fees

31 Aug - 1 Sept

A brick building with a gravel courtyard, a staircase, and potted plants.

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

Siena

Kathleen M.

HK$2,741 total

includes taxes & fees

7 Sept - 8 Sept

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

10. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

HK$43,982 total

includes taxes & fees

31 Aug - 1 Sept

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

11. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

HK$17,593 total

includes taxes & fees

14 Sept - 15 Sept

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

San Vivaldo

HK$13,462 total

includes taxes & fees

3 Sept - 4 Sept

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.

13. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

HK$4,133 total

includes taxes & fees

1 Sept - 2 Sept

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

14. Villa Torre Among the Hills of Siena

Vico dʼArbia

HK$16,035 total

includes taxes & fees

5 Sept - 6 Sept

An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

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

Impruneta

Maria H.

HK$3,209 total

includes taxes & fees

31 Aug - 1 Sept

A building with a large entrance, potted plants, and a statue in the foreground.

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

Montespertoli

Scott M.

HK$19,637 total

includes taxes & fees

1 Sept - 2 Sept

A villa with a swimming pool, surrounded by lush greenery and hills.

17. Villa Linchiano with Historic Tower and Private Pool

Gambassi Terme

HK$23,642 total

includes taxes & fees

19 Sept - 20 Sept

A rural property with stone buildings, a garden, and a view of rolling hills.

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

Montaione

HK$4,007 total

includes taxes & fees

9 Sept - 10 Sept

A person in a swimming pool with a view of a vineyard and hills.

19. "A Casa di Franca Villa con piscina"

Gambassi Terme

"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...

Anonymous traveller

HK$18,470 total

includes taxes & fees

30 Sept - 1 Oct

An outdoor dining area with a table set for four, surrounded by brick pillars and white chairs.

20. Villa Ludovica with private pool, Borgo del Silenzio

Lajatico

Carl P.

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Top Colle di Val d'Elsa Hotel Reviews

Villa Sabolini

10/10 Excellent

"We couldn’t rate Villa Sabolini more highly - we had such an excellent time. It is a beautiful property and the perfect place to relax and enjoy Tuscany. The staff were so helpful and friendly too."

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"WOW! What a beautiful place and awesome hosts! 15 of us traveled to celebrate several birthdays, to enjoy, to discover the area, eat well and create new experiences. For all of these I used the experience and recommendations of Jacopo and Beatrice. We maintained communication for 3 months, and everything turned out perfect! They are the perfect hosts and this is a perfect house whether you want to rest or use it as a base with a large group. The villa(house) is large, with plenty of to do's, with a nice pool and quiet surroundings. The pictures are accurate and the dinners from Beatrice are amazing. Do not hesitate to stay on this place, to pay for the villa and the experiences, and to work together with Jacopo and Beatrice for the perfect celebration and vacation. Don't skip taking a tour of local wineries and eating in one of the local restaurants. 100% Recommended!!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"This is a very special Tuscan style hotel in the beautiful countryside surrounded by vineyards and olive groves. The staff were excellent, special mention goes to Elisa ,and the food was amazing. My only feedback, if you pay for a treatment the other spa facilities should be included. Also, the gym is very small but let's I wasn't there to train."

Poderi Arcangelo

8/10 Good

"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the view and location, but worth noting. Breakfast was nice, we would have preferred a little more choice, but no complaints, they hosted a pizza night on one of our stays, the pizza was ok, we would have preferred to have the Tuscan dinner another night but didn’t work with our plans, All in all a lovely stay, would happily return."

Relais Della Rovere

10/10 Excellent

"We stayed here with our grown up children and their baby. The hotel was clean, well-maintained and very convenient to either drive or walk to the centre. The pool was clean and well maintained with plenty of sun beds for everyone all through the day so, happily, no one felt the need to “reserve” them. Breakfast was delicious with lots of options. We also had lunch and dinner once during our stay. The food was lovely. However, one of us eats gluten-free food and, despite ordering a dish that did not list gluten as an ingredient, it did have gluten-containing decorations on it so beware of that if it would affect you. The staff replaced the dish straight away though with one that was safe to eat. We made sure that we stressed the gluten-free need after that regardless of what the menu says. Our rooms were clean and very spacious with comfortable enormous beds which the parents of the baby were very grateful for as it easily fitted all three of them with room to spare. We all had a great time and would strongly recommend it. PS take some bug spray as there are mosquitoes around"

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