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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Montespertoli villas

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

1. 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 $9,417
CA $9,424 total
includes taxes & fees
Nov 15 - Nov 16
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

2. 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 $2,040
CA $2,221 total
includes taxes & fees
Nov 29 - Nov 30
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 a scenic countryside view.

3. 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 $2,590
CA $2,959 total
includes taxes & fees
Nov 8 - Nov 9
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
A building with a large entrance, potted plants, and a statue in the foreground.

4. 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 $2,543
CA $2,546 total
includes taxes & fees
Nov 6 - Nov 7
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A courtyard with a building, potted plants, and a grassy area.

5. 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
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

6. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is CA $173
CA $195 total
includes taxes & fees
Nov 6 - Nov 7
Rooster House, Cooking Classes, and Opera
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

7. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is CA $22,225
CA $22,225 total
includes taxes & fees
Nov 6 - Nov 7
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A stone building with a large arched entrance, potted plants, and outdoor seating.

8. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (117 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 $1,373
CA $1,555 total
includes taxes & fees
Nov 8 - Nov 9
Exclusive Estate | Personal Concierge & Heated Pool
A covered balcony with a brick railing, a bench, and a view of lush greenery.

9. 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 $1,633
CA $1,825 total
includes taxes & fees
Nov 8 - Nov 9
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A person in a swimming pool with a view of a vineyard and hills.

10. "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 $1,627
CA $2,397 total
includes taxes & fees
Nov 9 - Nov 10
"A Casa di Franca Villa con piscina"
A garden with potted plants and a metal fence, overlooking a valley with mountains in the distance.

11. Golden Hour - Wedding in Florence

Golden Hour - Wedding in Florence
Toscana
The price is CA $4,316
CA $4,668 total
includes taxes & fees
Nov 6 - Nov 7
Golden Hour - Wedding in Florence
A large, historic building with a tower, multiple arches, and a courtyard with outdoor seating.

12. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Careggi Rifredi
10.0 out of 10, Exceptional, (1 review)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
The price is CA $14,816
CA $14,816 total
includes taxes & fees
Nov 6 - Nov 7
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
A multi-story building with a courtyard, surrounded by trees and hills.

13. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Oltrarno
The price is CA $2,612
CA $2,631 total
includes taxes & fees
Nov 15 - Nov 16
Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

14. 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 $450
CA $499 total
includes taxes & fees
Nov 19 - Nov 20
Villa Montecastello
A poolside area with lounge chairs and a pergola.

15. Bagno a Ripoli, Italy. Entire property: Villa

Bagno a Ripoli, Italy. Entire property: Villa
Toscana
The price is CA $1,088
CA $1,171 total
includes taxes & fees
Nov 6 - Nov 7
Bagno a Ripoli, Italy. Entire property: Villa
A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

16. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Rignano sull'Arno
The price is CA $4,520
CA $7,724 total
includes taxes & fees
Nov 6 - Nov 7
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
A terrace with stone walls, a view of the landscape, and outdoor furniture including a chair and a table.

17. Antico Borghetto di Tigliano: Cozy and ideal for families with children

Antico Borghetto di Tigliano: Cozy and ideal for families with children
Vinci
The price is CA $720
CA $822 total
includes taxes & fees
Nov 6 - Nov 7
Antico Borghetto di Tigliano: Cozy and ideal for families with children
A hot tub with a wooden exterior, surrounded by lush greenery and a scenic view of hills.

18. Villa Dei Pavoni - Luxury Villa in the Hills of Florence

Villa Dei Pavoni - Luxury Villa in the Hills of Florence
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
United States
Leopard I.
The price is CA $2,486
CA $2,695 total
includes taxes & fees
Nov 6 - Nov 7
Villa Dei Pavoni - Luxury Villa in the Hills of Florence
A poolside area with wicker furniture, a bottle of champagne, and a tray with snacks and drinks.

19. Villa 'Podere Bucigattolo' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Podere Bucigattolo' with Private Pool, Wi-Fi and Air Conditioning
Serravalle pistoiese
10.0 out of 10, Exceptional, (3 reviews)
"Great villa for lager groups with great view. Very quite location. The road towards the villa is a bit narrow and makes going for a quick grocery trip a bit less easy. The beds and bathrooms are great although from the description we did not deduct that two rooms share a bathroom and are directly connected. The kitchen downstairs is well equipped but a bit small to accommodate 1 large group sharing the whole property. The host and her sister took great care of us and really nice to be able to...
United States
Maarten O.
The price is CA $3,514
CA $4,031 total
includes taxes & fees
Nov 6 - Nov 7
Villa 'Podere Bucigattolo' with Private Pool, Wi-Fi and Air Conditioning
A large estate with a swimming pool, tennis court, and multiple guest rooms.

20. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is CA $18,521
CA $18,521 total
includes taxes & fees
Nov 29 - Nov 30
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
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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Learn more about Montespertoli

Surrounded by vineyards, this Tuscan town invites you to sample Chianti wines at family-run estates like Castello Sonnino. Join cooking classes to master traditional pasta making, then explore the medieval castle tower for panoramic countryside views.

See all hotels in Montespertoli
A sunlit landscape with a dirt path, rolling hills, and a misty valley.

Frequently Asked Questions

How much do villas in Montespertoli cost?

You'll pay between CA $172 and CA $22,224 per night for a villa in Montespertoli. Whatever your budget, a fantastic stay is just a click or two away on 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 Montespertoli?

Pick from villas in Montespertoli. Whether you're taking a trip with the little ones or planning a weekend escape with some friends, Expedia can help you find the right space for your squad.

Why book your villa in Montespertoli with Expedia?

Booking a villa in Montespertoli is as easy as deciding on your travel dates and choosing an option suited to your needs. Looking for something upscale or budget friendly, or a stay that also offers a kitchen? Use Expedia's search filters to narrow your results and find your ideal match.

How can I find cheap villas in Montespertoli?

Expedia is here to help you easily locate cheap villas in Montespertoli. Simply use our filter tool to select star rating, budget and amenities to refine your search and find a great place to stay in a matter of clicks.

What is there to do near my villa in Montespertoli?

There are loads of fantastic things to sink your teeth into in Montespertoli. Drop by popular attractions like Vine and Wine Museum, Castle of Poppiano and Montespertoli City Hall. Piazza Machiavelli, Azienda Agricola Ammirabile and Montegufoni Castle also lure many visitors.