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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 ￥28,809
￥32,217 total
includes taxes & fees
Oct 28 - Oct 29
Villa Montecastello
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

2. 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 ￥1,144,604
￥1,232,467 total
includes taxes & fees
Oct 28 - Oct 29
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A stone building with a swimming pool, wooden deck, and a tall tree.

3. 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 ￥104,922
￥189,425 total
includes taxes & fees
Nov 2 - Nov 3
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

4. 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 ￥351,451
￥481,663 total
includes taxes & fees
Nov 6 - Nov 7
Villa Mami: A Tuscan retreat full of elegance and charm
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 ￥19,330
￥23,020 total
includes taxes & fees
Nov 6 - Nov 7
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 ￥154,041
￥192,876 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 ￥222,679
￥261,514 total
includes taxes & fees
Nov 3 - Nov 4
Villa Torre Among the Hills of Siena
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

8. 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 ￥268,860
￥273,077 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.

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 ￥183,112
￥204,575 total
includes taxes & fees
Nov 2 - Nov 3
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
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 ￥55,353
￥78,900 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥223,010
￥261,903 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 ￥298,733
￥341,962 total
includes taxes & fees
Nov 2 - Nov 3
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 vineyards.

13. 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 ￥948,917
￥949,620 total
includes taxes & fees
Nov 2 - Nov 3
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

14. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
Siena
The price is ￥959,179
￥959,179 total
includes taxes & fees
Oct 29 - Oct 30
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
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 traveler
The price is ￥182,155
￥268,403 total
includes taxes & fees
Nov 2 - Nov 3
"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 ￥284,675
￥285,026 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥289,947
￥331,945 total
includes taxes & fees
Nov 2 - Nov 3
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
A courtyard with a building, potted plants, and a grassy area.

18. 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 ￥351,451
￥402,060 total
includes taxes & fees
Nov 2 - Nov 3
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
Pool

19. 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 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 ￥116,580
￥160,144 total
includes taxes & fees
Nov 3 - Nov 4
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 Minerva

Hotel Minerva

10/10 Excellent
"Clean, great breakfast, lovely view!"
Tracy 2-night trip
Posted 8 hours ago
Hotel Minerva

Find out more about Monteriggioni

Monteriggioni Villas information

Number of reviews
81
Accommodation
1583 Villas
Lowest Price
￥23,020
Highest Price
￥1,232,467

Frequently asked questions

How much do villas in Monteriggioni cost?
Villas in Monteriggioni cost between ￥23,020 and ￥1,232,467 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 1583 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.