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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 Montecastelli holiday rentals

A garden with a stone pathway, wooden benches, and various potted plants.

1. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (87 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ฿5,070
฿5,765 total
includes taxes & fees
13 Oct - 14 Oct
Antico Borgo il Cardino
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

2. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ฿5,007
฿5,583 total
includes taxes & fees
25 Oct - 26 Oct
Palazzo Pacini
A stone building with a tiled roof, a brick pathway, and a small grassy area.

3. Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
The price is ฿6,828
฿7,586 total
includes taxes & fees
13 Oct - 14 Oct
Le Mascie Country House
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

4. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is ฿4,010
฿7,077 total
includes taxes & fees
14 Oct - 15 Oct
Borgo Il Poggiaccio
A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

5. Nido con vista

Nido con vista
Radicondoli
The price is ฿5,070
฿5,577 total
includes taxes & fees
11 Nov - 12 Nov
Nido con vista
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

6. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ฿2,220
฿2,555 total
includes taxes & fees
4 Nov - 5 Nov
Tuscasì Aparthotel
Outdoor pool

7. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is ฿4,456
฿5,014 total
includes taxes & fees
9 Nov - 10 Nov
Residence Arianna
A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

8. AlbergoDiffusoVolterra

AlbergoDiffusoVolterra
Volterra
8.6 out of 10, Excellent, (19 reviews)
"Lovely stay at a little gem in Volterra. Enrico the owner has created a great concept with different apartments around the city and the restaurant is serving delicious local plant based food. Don’t miss the cheesecake ❤️"
Sweden
Mia
The price is ฿4,003
฿5,681 total
includes taxes & fees
13 Oct - 14 Oct
AlbergoDiffusoVolterra
A stone building with outdoor seating and a view of the countryside.

9. Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is ฿5,685
฿6,366 total
includes taxes & fees
13 Oct - 14 Oct
Antico Borgo Poggiarello
A building with a stucco exterior, multiple windows, and a tiled roof.

10. Residence Il Paradiso

Residence Il Paradiso
3.0 star property
Guardistallo
8.4 out of 10, Very good, (27 reviews)
"Absolutely beautiful property among the pine trees. Nice little restaurant, ideal pools and play area for little kids. Location is perfect for exploring the region. Great beaches only 10-15 minutes away. The apartment was very clean and everything necessary for our stay was available. Would gladly visit again. Thank you Il Paradiso!"
Germany
Jason
The price is ฿2,447
฿2,692 total
includes taxes & fees
13 Oct - 14 Oct
Residence Il Paradiso
A stone courtyard with a bench, potted plants, and a building in the background.

11. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is ฿3,392
฿3,844 total
includes taxes & fees
8 Nov - 9 Nov
Casa di Campagna in Toscana
A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

12. Beatabb

Beatabb
Guardistallo
9.4 out of 10, Exceptional, (19 reviews)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
The price is ฿2,719
฿2,991 total
includes taxes & fees
13 Oct - 14 Oct
Beatabb
A narrow street with stone buildings, a tower, and an archway.

13. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is ฿3,534
฿4,075 total
includes taxes & fees
3 Nov - 4 Nov
Materia Rooms San Gimignano
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

14. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is ฿3,081
฿3,577 total
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
A rustic stone building with a courtyard.

15. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is ฿3,568
฿4,075 total
includes taxes & fees
13 Oct - 14 Oct
Fullino Nero
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

16. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ฿5,811
฿6,467 total
includes taxes & fees
19 Oct - 20 Oct
Riserva di Fizzano Residence
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

17. 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 ฿6,219
฿6,954 total
includes taxes & fees
16 Oct - 17 Oct
Villa Montecastello
A reception desk with the word "SPORTLAND" prominently displayed.

18. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is ฿1,493
฿1,718 total
includes taxes & fees
18 Oct - 19 Oct
Sportland
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

19. Tenuta Quadrifoglio

Tenuta Quadrifoglio
Gambassi Terme
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is ฿4,302
฿4,845 total
includes taxes & fees
19 Oct - 20 Oct
Tenuta Quadrifoglio
A stone building with a tiled roof, surrounded by lush greenery and a wooden pergola.

20. Apartment in Chianti With Pool ID 450

Apartment in Chianti With Pool ID 450
Casole d'Elsa
The price is ฿15,072
฿16,655 total
includes taxes & fees
13 Oct - 14 Oct
Apartment in Chianti With Pool ID 450
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 Montecastelli Hotel Reviews

Hotel Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"This was one of the greatest hotel experiences we’ve had. The property is top notch. The staff are amazing. We plan on coming back for sure. It it centrally located to great sights and wineries, everything seemed to be 20 to 30 minutes away."
Joseph 4-night trip
Posted 18 hours ago
Hotel Borgo San Luigi

Find out more about Montecastelli

Search for holiday rentals in Montecastelli on Expedia! You can easily find your home rentals, villas, holiday apartments in Montecastelli using one of the methods below:

  • View our selection of featured holiday rentals in Montecastelli
  • Use the map to find apartments and other holiday homes in the Montecastelli neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montecastelli while they last

Look no further and take a look at our great range of rental properties in Montecastelli!

Frequently asked questions

Are there holiday rentals in Montecastelli?

Yes, there are holiday rentals close to the most popular sights in Montecastelli, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals will I find in Montecastelli?

Expedia has 16 holiday rentals for your stay in Montecastelli.

What can I see and do in Montecastelli?

Explore the area and family-friendly sights such as Terre di Vini, or get out into nature at a spot like Sentierelsa Trail. In the wider area, you’ll find Medici Fortress and Porta all'Arco.

What are holiday rentals like in Montecastelli?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montecastelli. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family getaway.