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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Monteriggioni 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 $452
CA $502 total
includes taxes & fees
Nov 26 - Nov 27
Villa Montecastello
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

2. 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 $3,161
CA $4,100 total
includes taxes & fees
Nov 29 - Nov 30
Villa Mami: A Tuscan retreat full of elegance and charm
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

3. 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 $11,191
CA $11,981 total
includes taxes & fees
Nov 13 - Nov 14
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A large estate with a swimming pool, tennis court, and multiple guest rooms.

4. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is CA $18,651
CA $18,651 total
includes taxes & fees
Nov 29 - Nov 30
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
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
7.4 out of 10, Good, (3 reviews)
"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...
United States
JIm B.
The price is CA $944
CA $1,704 total
includes taxes & fees
Nov 29 - Nov 30
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A dining area with a wooden table, white chairs, and a chandelier.

6. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
The price is CA $476
CA $476 total
includes taxes & fees
Nov 30 - Dec 1
Villa Liberty in The Centre - No Ztl
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

7. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is CA $174
CA $196 total
includes taxes & fees
Nov 26 - Nov 27
Rooster House, Cooking Classes, and Opera
A stone building with a tower, surrounded by trees and a garden.

8. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is CA $1,386
CA $1,735 total
includes taxes & fees
Nov 15 - Nov 16
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

9. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,003
CA $2,352 total
includes taxes & fees
Nov 15 - Nov 16
Villa Torre Among the Hills of Siena
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

10. 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 $2,424
CA $2,462 total
includes taxes & fees
Nov 15 - Nov 16
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A covered balcony with a brick railing, a bench, and a view of lush greenery.

11. 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 $1,645
CA $1,837 total
includes taxes & fees
Nov 15 - Nov 16
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
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 $8,535
CA $8,542 total
includes taxes & fees
Nov 15 - Nov 16
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

13. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $2,003
CA $2,352 total
includes taxes & fees
Nov 15 - Nov 16
Villa Capanna: A Window onto Tuscany
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

14. 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 $2,055
CA $2,229 total
includes taxes & fees
Nov 29 - Nov 30
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A person in a swimming pool with a view of a vineyard and hills.

15. "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 $1,638
CA $2,414 total
includes taxes & fees
Nov 16 - Nov 17
"A Casa di Franca Villa con piscina"
A building with a large entrance, potted plants, and a statue in the foreground.

16. 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 $2,561
CA $2,564 total
includes taxes & fees
Nov 17 - Nov 18
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

17. 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 $1,976
CA $2,263 total
includes taxes & fees
Dec 9 - Dec 10
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

18. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is CA $1,049
CA $1,440 total
includes taxes & fees
Nov 17 - Nov 18
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
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 Monteriggioni

This perfectly preserved medieval walled town lets you walk the complete circuit of 14th-century fortifications for panoramic Tuscan countryside views. Inside the walls, Piazza Roma and the Church of Santa Maria Assunta offer glimpses into the town's rich history that inspired scenes in 'Assassin's Creed.'

See all hotels in Monteriggioni
A historic castle on a hill with surrounding vineyards and a small house.

Frequently Asked Questions

How much do villas in Monteriggioni cost?

Villas in Monteriggioni cost between CA $173 and CA $18,651 per night. These stays give you the privacy of your own space at a price that's friendly to your wallet. 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 Monteriggioni?

Monteriggioni has villas to pick from. Find your next perfect stay quickly and easily by clicking the "Villa" checkbox under the "Property type" tab in our filter tool.

Why book your villa in Monteriggioni with Expedia?

We think vacation time should be a breeze, so if you're searching for villas at a nice price, Expedia is here to help. Keep the budget under control and choose an all-inclusive stay, or splurge on a 5-star villa to spoil the ones you love most. Take advantage of our search filters to find a place in Monteriggioni that matches your needs.

How can I find cheap villas in Monteriggioni?

A fantastic way to track down cheap villas in Monteriggioni is with Expedia's handy filter tool. Refine your search results by budget, star rating and amenities to grab unbeatable deals in only a couple of clicks.

What is there to do near my villa in Monteriggioni?

After you've settled into your villa, set out and discover the awesome things Monteriggioni has on offer. San Leonardo al Lago is a top attraction to add to your must-do list.