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Montecastelli Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Montecastelli vacation rentals

A stone building with a patio area, outdoor seating, and a fire pit.

1. Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi

Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi
Castelnuovo di Val di Cecina
9.0 out of 10, Wonderful, (2 reviews)
"We had the best time in this beautiful place! The location is absolutely stunning — the garden, house, pool, and everything was perfect and very clean. Tamara is super friendly and kind; she even brought us fresh bread every morning and sold us her delicious honey! Her two dogs are also very sweet and added to the warm, welcoming vibe of the place. The space is very spacious and a truly beautiful corner of nature that you must see.Thank you again, Tamara, for everything!"
Germany
Lea B.
The price is ￥261,436
￥285,929 total
includes taxes & fees
Sep 19 - Sep 20
Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi

2. A Nest with a View - A Romantic Retreat Within the City Walls

A Nest with a View - A Romantic Retreat Within the City Walls
Radicondoli
The price is ￥31,553
￥31,553 total
includes taxes & fees
Aug 28 - Aug 29
A Nest with a View - A Romantic Retreat Within the City Walls
A rustic kitchen with a brick archway, wooden beams, and a dining table set for four.

3. Bellavista Farmhouse

Bellavista Farmhouse
Radicondoli
9.0 out of 10, Wonderful, (2 reviews)
"Tutto ok, peccato manca aria condizionata.. ci sono tanti ventilatori.. ma con queste estati torride non bastano più.. zero zanzare .. location bella.. piscina vicinissima e spazio all’aperto privato top."
Italy
Valentina
Bellavista Farmhouse
An outdoor seating area with wooden chairs and tables, stone walls, and a yellow building in the background.

4. Apartment "Radicondoli House" with Balcony & Wi-Fi

Apartment "Radicondoli House" with Balcony & Wi-Fi
Radicondoli Siena
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful apartment that is well decorated and comfortable with everything you could need Walkable to grocery store and restaurants Parking is free and close by Giovanna was so helpful and excellent communication Can't say enough about this place! "
United States
Corey
The price is ￥52,967
￥69,945 total
includes taxes & fees
Sep 2 - Sep 3
Apartment "Radicondoli House" with Balcony & Wi-Fi
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, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ￥26,467
￥30,042 total
includes taxes & fees
Aug 31 - Sep 1
Antico Borgo il Cardino
A dining area with a table set for four, a large window with an arched ceiling, and a view of the outdoors.

6. La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
casole d'elsa siena
10.0 out of 10, Exceptional, (43 reviews)
"We stayed in this beautiful clean, fully airconditioned apartment for 12 days, perfect location for trips to the surrounding area like Siena, Florence, Monteriggioni, Volterra & San Gimignano. The apartment is situated in a peaceful Agriturismo with lots of privacy and a great swimming pool. The owners are really hospitable and you feel welcome right away. Highly recommendable."
Netherlands
Linda T.
The price is ￥42,690
￥68,118 total
includes taxes & fees
Sep 12 - Sep 13
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
A stone building with a large tree in front, outdoor seating with tables and chairs, and a view of the surrounding landscape.

7. Borgo al Cerro

Borgo al Cerro
Casole d'Elsa
9.2 out of 10, Wonderful, (25 reviews)
"Väldigt vackert ställe med bra placering mitt i Toscana. Rummet var väldigt fint, men bilderna från hemsidan var finare, så jag blev lite besviken när vi väl kom in. I övrigt var komplexets omgivningar och trädgård helt fantastisk. Barnen hade roligt med pingisbor och dart och det fanns trevlig grillplats att nyttja. "
Sweden
Frida
The price is ￥34,196
￥38,545 total
includes taxes & fees
Sep 4 - Sep 5
Borgo al Cerro
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

8. 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 ￥25,285
￥40,991 total
includes taxes & fees
Sep 13 - Sep 14
Borgo Il Poggiaccio
A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

9. 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 ￥18,183
￥26,311 total
includes taxes & fees
Aug 28 - Aug 29
AlbergoDiffusoVolterra
A statue in a garden with a pool and lounge chairs.

10. Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
Toscana
The price is ￥50,114
￥72,572 total
includes taxes & fees
Aug 28 - Aug 29
Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

11. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ￥20,808
￥23,260 total
includes taxes & fees
Sep 1 - Sep 2
Palazzo Pacini
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

12. 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 ￥29,815
￥33,354 total
includes taxes & fees
Sep 27 - Sep 28
Villa Montecastello
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

13. House with pool for 4 pax

House with pool for 4 pax
Casole d'Elsa
9.4 out of 10, Exceptional, (3 reviews)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is ￥29,697
￥54,754 total
includes taxes & fees
Sep 24 - Sep 25
House with pool for 4 pax
A table set outdoors with fruits, a pitcher of red drink, and a vase of flowers.

14. Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning
Colle di Val d'Elsa
10.0 out of 10, Exceptional, (1 review)
"Pros: ***** einfach alles :)"
Germany
Anonymous traveler
The price is ￥51,865
￥60,230 total
includes taxes & fees
Sep 4 - Sep 5
Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning
A view from a window of a garden with a pathway, trees, and a distant landscape.

15. CANONICA 43 Luxury villa in the heart of Tuscany

CANONICA 43 Luxury villa in the heart of Tuscany
colle di val d'elsa
10.0 out of 10, Exceptional, (14 reviews)
"We had a very plezant stay!"
Netherlands
Ann R.
The price is ￥77,955
￥118,417 total
includes taxes & fees
Sep 8 - Sep 9
CANONICA 43 Luxury villa in the heart of Tuscany
A cozy room with a wooden ceiling, a dining table set with plates, cups, and a vase, and a sofa with a book on it.

16. Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access

Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
Località Gerfalco Montieri
The price is ￥54,661
￥60,229 total
includes taxes & fees
Sep 3 - Sep 4
Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
A view from a window overlooking a rural landscape with fields and a distant mountain range.

17. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 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 ￥22,540
￥25,723 total
includes taxes & fees
Aug 30 - Aug 31
B&B Palazzo Tortoli
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.

18. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥12,101
￥15,724 total
includes taxes & fees
Aug 31 - Sep 1
Tuscasì Aparthotel

19. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (7 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is ￥21,580
￥24,295 total
includes taxes & fees
Sep 17 - Sep 18
Residence Arianna
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, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is ￥20,245
￥23,198 total
includes taxes & fees
Sep 25 - Sep 26
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

Poderi Arcangelo

Poderi Arcangelo

8/10 Good
"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the view and location, but worth noting. Breakfast was nice, we would have preferred a little more choice, but no complaints, they hosted a pizza night on one of our stays, the pizza was ok, we would have preferred to have the Tuscan dinner another night but didn’t work with our plans, All in all a lovely stay, would happily return."
Nicholas 2-night trip
Posted 1 day ago
Poderi Arcangelo

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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  • 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 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.

What are some of the best vacation rentals that Montecastelli has to offer?

Holiday house with private pool and fenced garden: This vacation home rental outside of Montecastelli is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Alta Val d'Elsa River Park. In the larger area, you’ll find Medici Fortress and Cathedral of Volterra.

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.