A cobblestone square with historic buildings, a fountain, and a church with a bell tower.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 $242
CA $271 total
includes taxes & fees
Oct 26 - Oct 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 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 $3,178
CA $4,356 total
includes taxes & fees
Oct 19 - Oct 20
Villa Mami: A Tuscan Retreat 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 $10,352
CA $11,146 total
includes taxes & fees
Oct 19 - Oct 20
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A stone building with a swimming pool, wooden deck, and a tall tree.

4. 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 $1,605
CA $2,369 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

5. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is CA $175
CA $208 total
includes taxes & fees
Oct 19 - Oct 20
Rooster House, cooking classes and opera
A stone building with a tower, surrounded by trees and a garden.

6. 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 $1,548
CA $1,899 total
includes taxes & fees
Nov 2 - Nov 3
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

7. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is CA $2,238
CA $2,589 total
includes taxes & fees
Nov 2 - Nov 3
Villa Torre Among the Hills of Siena
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

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 $733
CA $926 total
includes taxes & fees
Oct 19 - Oct 20
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

9. 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 $2,861
CA $2,899 total
includes taxes & fees
Nov 3 - Nov 4
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and 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.

10. 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 $501
CA $725 total
includes taxes & fees
Oct 19 - Oct 20
Villa Il Signorino
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

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is CA $2,238
CA $2,589 total
includes taxes & fees
Nov 2 - Nov 3
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.

12. 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 $2,702
CA $3,005 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

13. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is CA $8,675
CA $8,675 total
includes taxes & fees
Oct 19 - Oct 20
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
A villa with a swimming pool, surrounded by lush greenery and vineyards.

14. 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 $8,582
CA $8,588 total
includes taxes & fees
Oct 19 - Oct 20
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.

15. 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 $2,575
CA $2,578 total
includes taxes & fees
Nov 1 - Nov 2
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A person in a swimming pool with a view of a vineyard and hills.

16. "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 $1,647
CA $2,427 total
includes taxes & fees
Nov 2 - Nov 3
"A Casa di Franca Villa con piscina"
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 $2,622
CA $2,916 total
includes taxes & fees
Nov 1 - Nov 2
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Terrace/patio

18. 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
A courtyard with a building, potted plants, and a grassy area.

19. 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 $3,178
CA $3,534 total
includes taxes & fees
Nov 1 - Nov 2
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A rustic stone building with a balcony, surrounded by lush greenery and flowering plants.

20. 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 $1,054
CA $1,448 total
includes taxes & fees
Nov 1 - Nov 2
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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Top Monteriggioni Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"It was OK for the price. The breakfast was so so, the parking very small and often full. The building is old and was making weird noises occasionally. The location was excellent: just outside LTZ but very close to all the points of interest."
Victor 4-night trip
Posted 3 days ago
Hotel Chiusarelli

Find out more about Monteriggioni

Monteriggioni Villas information

Number of reviews
81
Accommodation
1572 Villas
Lowest Price
CA $208
Highest Price
CA $11,146

Frequently asked questions

How much do villas in Monteriggioni cost?
Villas in Monteriggioni cost between CA $208 and CA $11,146 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 1572 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.