Val d'Elsa Villas from CA $165

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Our top choices for Val d'Elsa villas

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

1. Villa Montecastello

Monteriggioni

Alvaro

CA $500 total

includes taxes & fees

Nov 11 - Nov 12

A large estate with a swimming pool, tennis court, and multiple guest rooms.

2. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

CA $18,577 total

includes taxes & fees

Nov 29 - Nov 30

3. Villa LE Cascine

Montaione

CA $4,051 total

includes taxes & fees

Nov 24 - Nov 25

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

Certaldo - Firenze

Kelly C.

CA $1,830 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Montespertoli

Scott M.

CA $2,554 total

includes taxes & fees

Nov 11 - Nov 12

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

6. "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

CA $2,405 total

includes taxes & fees

Nov 10 - Nov 11

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

7. Rooster House, Cooking Classes, and Opera

Tavarnelle Val di Pesa

CA $195 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with a view of the landscape, surrounded by greenery and a pergola structure.

8. Villa Le Polle di Meletro

Rivalto

CA $327 total

includes taxes & fees

Nov 10 - Nov 11

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

9. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

CA $11,933 total

includes taxes & fees

Nov 10 - Nov 11

A stone building with a garden pathway leading to it.

10. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino

CA $10,076 total

includes taxes & fees

Nov 10 - Nov 11

An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

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

Toscana

CA $4,090 total

includes taxes & fees

Nov 10 - Nov 11

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

Montespertoli

CA $8,508 total

includes taxes & fees

Nov 15 - Nov 16

A stone building with a large arched entrance, potted plants, and outdoor seating.

13. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

impruneta

Oli P.

CA $2,017 total

includes taxes & fees

Nov 10 - Nov 11

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

14. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

CA $2,343 total

includes taxes & fees

Nov 10 - Nov 11

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

15. Villa Torre Among the Hills of Siena

Vico dʼArbia

CA $2,343 total

includes taxes & fees

Nov 10 - Nov 11

A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

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

Montespertoli

Krista G.

CA $2,220 total

includes taxes & fees

Nov 29 - Nov 30

A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

17. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

CA $22,292 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Radda in Chianti

"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...

JIm B.

CA $1,697 total

includes taxes & fees

Nov 11 - Nov 12

A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

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

Montespertoli

"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!"

Elise D.

CA $2,254 total

includes taxes & fees

Dec 9 - Dec 10

A kitchen with a stone wall, a wooden cabinet, a white countertop, and a white sink.

20. Demeure Tournesols: Your rustic home in the heart of all of Tuscany's top destinations!

Toscana

CA $390 total

includes taxes & fees

Nov 22 - Nov 23

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Learn more about Val d'Elsa

Discover the historic area of Val d'Elsa—wineries, pristine countryside, and sights from Colle di Val d'Elsa Cathedral to Museo del Cristallo di Colle di Val d'Elsa.

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A historic stone building with tall towers and a bell tower.

Frequently Asked Questions

How much do villas in Val d'Elsa cost?

Prices for villas in Val d'Elsa range between CA $165 and CA $22,292 per night. Whatever your budget, you can find a place that fits your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Val d'Elsa?

Val d'Elsa has villas to pick from. Find your next perfect stay quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.

Why book your villa in Val d'Elsa with Expedia?

Booking a villa in Val d'Elsa is as simple as clicking on your travel dates and selecting an option that has what you need. Seeking something luxurious or affordable, or a stay that also features a pool? Use Expedia's search filters to narrow your results and find the perfect fit.

How can I find cheap villas in Val d'Elsa?

Expedia is here to help you track down cheap villas in Val d'Elsa. Simply use our filter tool to select star rating, budget and amenities to refine your search and find an amazing place to stay in a matter of clicks.

What is there to do near my villa in Val d'Elsa?

Whatever you love doing, Val d'Elsa has plenty to keep you on the move. San Lucchese Convent, Magione Castle and Fountain of Fate are on many travelers' itineraries. Don't forget to explore Church of San Lorenzo, Piazza Arnolfo di Cambio and Tenuta Torciano Winery either. With Expedia's Val d'Elsa hotel deals, you'll be able to see more awesome attractions like these with the money you save.

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Search Val d'Elsa Villa Rentals from CA $165

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Val d'Elsa villas

1. Villa Montecastello

2. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

3. Villa LE Cascine

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

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

6. "A Casa di Franca Villa con piscina"

7. Rooster House, Cooking Classes, and Opera

8. Villa Le Polle di Meletro

9. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

10. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

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

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

13. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

14. Villa Capanna: A Window onto Tuscany

15. Villa Torre Among the Hills of Siena

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

17. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

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

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

20. Demeure Tournesols: Your rustic home in the heart of all of Tuscany's top destinations!

Learn more about Val d'Elsa

Frequently Asked Questions

How much do villas in Val d'Elsa cost?

How many villas are there in Val d'Elsa?

Why book your villa in Val d'Elsa with Expedia?

How can I find cheap villas in Val d'Elsa?

What is there to do near my villa in Val d'Elsa?

Explore a world of travel with Expedia