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Montecastelli Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Montecastelli vacation rentals

An interior with stone walls, wooden doors, and a bar area with stools and bottles.

1. 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 P7,285
P13,032 total
includes taxes & fees
Oct 14 - Oct 15
Borgo Il Poggiaccio
Outdoor pool

2. 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 P9,592
P10,762 total
includes taxes & fees
Nov 8 - Nov 9
Residence Arianna
A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

3. Nido con vista

Nido con vista
Radicondoli
The price is P9,598
P10,558 total
includes taxes & fees
Nov 6 - Nov 7
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.

4. 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 P3,901
P5,205 total
includes taxes & fees
Nov 2 - Nov 3
Tuscasì Aparthotel
A garden with a stone pathway, wooden benches, and various potted plants.

5. 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 P9,540
P10,848 total
includes taxes & fees
Oct 13 - Oct 14
Antico Borgo il Cardino
A stone courtyard with a bench, potted plants, and a building in the background.

6. 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 P6,383
P7,234 total
includes taxes & fees
Nov 2 - Nov 3
Casa di Campagna in Toscana
A stone building with a tiled roof, a brick pathway, and a small grassy area.

7. 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 P12,849
P14,275 total
includes taxes & fees
Oct 21 - Oct 22
Le Mascie Country House
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

8. 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 P8,333
P9,306 total
includes taxes & fees
Nov 7 - Nov 8
Palazzo Pacini
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 P10,697
P11,979 total
includes taxes & fees
Oct 11 - Oct 12
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 P4,604
P5,065 total
includes taxes & fees
Oct 14 - Oct 15
Residence Il Paradiso
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

11. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is P3,354
P3,901 total
includes taxes & fees
Oct 9 - Oct 10
Camping Boschetto Di Piemma
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 P5,116
P5,628 total
includes taxes & fees
Oct 12 - Oct 13
Beatabb
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 P7,533
P10,689 total
includes taxes & fees
Oct 12 - Oct 13
AlbergoDiffusoVolterra
An open wooden door leading to an outdoor patio with a table and chairs.

14. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 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 P6,065
P8,791 total
includes taxes & fees
Nov 2 - Nov 3
Palazzo al Torrione 2
A reception desk with the word "SPORTLAND" prominently displayed.

15. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

16. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 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 P5,798
P6,731 total
includes taxes & fees
Nov 2 - Nov 3
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

Mormoraia

Mormoraia

10/10 Excellent
"This place is stunningly beautiful a heaven on Earth. I’ve traveled all over Italy and"
Lauren 2-night trip
Posted 17 hours ago
Mormoraia

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

Frequently asked questions

Are there vacation rentals in Montecastelli?

Yes, we offer vacation rentals close to top points of interest in Montecastelli, or you can select a more remote option if you're looking for a relaxing stay.

How many vacation rentals will I find in Montecastelli?

Expedia has 16 vacation 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 larger area, you’ll find Medici Fortress and Porta all'Arco.

What are vacation rentals like in Montecastelli?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Montecastelli. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.