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Montecastelli Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Montecastelli holiday rentals

A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

1. Nido con vista

Nido con vista
Radicondoli
The price is RM710
RM781 total
includes taxes & fees
28 Sept - 29 Sept
Nido con vista
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

2. 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 RM376
RM743 total
includes taxes & fees
29 Sept - 30 Sept
Borgo Il Poggiaccio
A garden with a stone pathway, wooden benches, and various potted plants.

3. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is RM626
RM712 total
includes taxes & fees
19 Oct - 20 Oct
Antico Borgo il Cardino
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

4. 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 RM550
RM614 total
includes taxes & fees
26 Oct - 27 Oct
Palazzo Pacini
A stone building with a tiled roof, a brick pathway, and a small grassy area.

5. 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
Le Mascie Country House
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

6. 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 RM692
RM775 total
includes taxes & fees
3 Oct - 4 Oct
Villa Montecastello

7. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (8 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 RM551
RM620 total
includes taxes & fees
28 Sept - 29 Sept
Residence Arianna
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

8. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (39 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is RM817
RM908 total
includes taxes & fees
29 Sept - 30 Sept
Riserva di Fizzano Residence
An open wooden door leading to an outdoor patio with a table and chairs.

9. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is RM436
RM618 total
includes taxes & fees
2 Oct - 3 Oct
Palazzo al Torrione 2
A stone building with outdoor seating and a view of the countryside.

10. 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 RM702
RM787 total
includes taxes & fees
26 Oct - 27 Oct
Antico Borgo Poggiarello
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.

11. 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 RM293
RM382 total
includes taxes & fees
25 Oct - 26 Oct
Tuscasì Aparthotel
A stone courtyard with a bench, potted plants, and a building in the background.

12. 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 RM437
RM494 total
includes taxes & fees
27 Oct - 28 Oct
Casa di Campagna in Toscana
A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

13. 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 RM472
RM677 total
includes taxes & fees
28 Sept - 29 Sept
AlbergoDiffusoVolterra
A reception desk with the word "SPORTLAND" prominently displayed.

14. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is RM185
RM212 total
includes taxes & fees
4 Oct - 5 Oct
Sportland

15. Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (99 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is RM629
RM715 total
includes taxes & fees
10 Oct - 11 Oct
Residence Borgo San Lorenzo a Linari
A view from a window overlooking a rural landscape with fields and a distant mountain range.

16. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is RM565
RM645 total
includes taxes & fees
18 Oct - 19 Oct
B&B Palazzo Tortoli
A narrow street with stone buildings, a tower, and an archway.

17. 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
Materia Rooms San Gimignano
A well-maintained garden with a central fountain, surrounded by lush greenery and flowering plants.

18. 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 RM532
RM599 total
includes taxes & fees
20 Oct - 21 Oct
Tenuta Quadrifoglio
A rustic stone building with a courtyard.

19. 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 RM403
RM462 total
includes taxes & fees
27 Sept - 28 Sept
Fullino Nero
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

20. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is RM521
RM596 total
includes taxes & fees
4 Oct - 5 Oct
Casa Vacanze Le Case
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

Villa Sabolini

Villa Sabolini

8/10 Good
"Beautiful 14th century villa in the Tuscan hills with very pretty pool and restaurant areas, and very helpful and friendly staff. The food was hearty and enjoyable, but not the highest standard, even compared to restaurants in the area. It's in a great location for exploring Florence, Chianti region and Siena. The room we used (superior garden view) was good, very interesting features due to the age of the property, with a stunning view. However, it was not very cosy for spending time in and the A/C struggled as well. Overall we were very happy with our choice and had a great stay!"
Morgan 10-night trip
Posted 1 day ago
Villa Sabolini

Find out more about Montecastelli

Search for holiday rentals in Montecastelli on Expedia.co.uk! 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
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  • 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 Val di Merse. 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.