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

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 AU$279
includes taxes & fees
26 Oct - 27 Oct
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 AU$4,210
includes taxes & fees
19 Oct - 20 Oct
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 AU$11,347
includes taxes & fees
31 Oct - 1 Nov
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 AU$2,415
includes taxes & fees
1 Nov - 2 Nov
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 AU$215
includes taxes & fees
19 Oct - 20 Oct
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 AU$1,866
includes taxes & fees
18 Oct - 19 Oct
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 AU$2,530
includes taxes & fees
18 Oct - 19 Oct
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 AU$943
includes taxes & fees
31 Oct - 1 Nov
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 AU$2,951
includes taxes & fees
16 Nov - 17 Nov
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 AU$716
includes taxes & fees
18 Oct - 19 Oct
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 AU$2,534
includes taxes & fees
18 Oct - 19 Oct
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 AU$3,011
includes taxes & fees
16 Nov - 17 Nov
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 AU$8,831
includes taxes & fees
29 Oct - 30 Oct
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 AU$8,756
includes taxes & fees
18 Oct - 19 Oct
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 AU$2,624
includes taxes & fees
1 Nov - 2 Nov
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 AU$2,471
includes taxes & fees
2 Nov - 3 Nov
"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 21 or +people with Sw-Pool,Wi-Fi,Airco

Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
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 AU$2,923
includes taxes & fees
16 Nov - 17 Nov
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
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 AU$3,595
includes taxes & fees
1 Nov - 2 Nov
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 AU$1,477
includes taxes & fees
1 Nov - 2 Nov
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"We had the most amazing stay in this beautiful hotel. Our room was so charming, and the entire hotel felt warm and welcoming in the most Italian way. Breakfast each morning included a beautiful spread of savory and sweet, and croissants that were better than Paris. The terrace sunsets looking over Siena welcomed us each evening after a long day of walking. Location was top notch. Our only “complaint” was that the bed was VERY firm. We will be back!!"
susan 7-night trip
Posted 8 hours ago
Palazzo Ravizza

Find out more about Monteriggioni

Monteriggioni Villas information

Number of reviews
81
Accommodation
1314 Villas
Lowest Price
AU$215
Highest Price
AU$11,347

Frequently asked questions

How much do villas in Monteriggioni cost?
You'll pay between AU$215 and AU$11,347 per night for a villa in Monteriggioni. No matter your budget, the perfect stay is just clicks away on Expedia. This price was 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?
Use up your holiday days and choose from 1314 villas in Monteriggioni. For a holiday with the family, a getaway with pals or anything in between, Expedia can help you find the perfect space in a few easy clicks.
What is there to do near my villa in Monteriggioni?
Monteriggioni has enough sights and experiences to keep you going for weeks, beginning with Siena Cathedral. Monteriggioni Castle, Palazzo Pubblico and Castello di Monsanto are other terrific attractions. If you're lingering longer, Castello della Paneretta and Civic Museum are worthwhile additions to your itinerary.

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