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Montecastelli Holiday Rentals

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Our top choices for Montecastelli holiday rentals

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 NZ$3,009
includes taxes & fees
19 Sept - 20 Sept
Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi

2. 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 NZ$736
includes taxes & fees
24 Aug - 25 Aug
Apartment "Radicondoli House" with Balcony & Wi-Fi

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
The price is NZ$955
includes taxes & fees
30 Aug - 31 Aug
Bellavista Farmhouse

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 NZ$423
includes taxes & fees
13 Sept - 14 Sept
Borgo Il Poggiaccio

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 NZ$310
includes taxes & fees
6 Sept - 7 Sept
Antico Borgo il Cardino

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 NZ$703
includes taxes & fees
12 Sept - 13 Sept
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

7. Tuscan Countryside Stay

Tuscan Countryside Stay
Casole d'Elsa
9.2 out of 10, Wonderful, (34 reviews)
"We had a fantastic time here! The swimming pool was refreshing, and we enjoyed cooking in the bright kitchen, The nearby town of Casole d’Elsa had charming shops and great places to eat, Highly recommend for a relaxing getaway!"
United States
Anonymous traveller
Tuscan Countryside Stay

8. 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 NZ$754
includes taxes & fees
24 Aug - 25 Aug
Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

9. 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 NZ$397
includes taxes & fees
4 Sept - 5 Sept
Borgo al Cerro

10. Casale Torricella: Relax in the Woods with Sea View

Casale Torricella: Relax in the Woods with Sea View
Montieri
10.0 out of 10, Exceptional, (1 review)
"Pros: Die Lage von Casale Torricella ist traumhaft. Die absolute Ruhe. Man hört lediglich Vogelgezwitscher und trotzdem ist Montieri mit seinem kleinen Supermetcado und 2 empfehlenswerter Lokalen nicht weit entfernt Der unbeschreibliche Duft, der in den Morgenstunden von all den Wildpflanzen ausgeht. Die supernetten Vermieter. Ich könnte stundenlang weiter schwärmen."
Germany
Anonymous traveller
The price is NZ$977
includes taxes & fees
10 Sept - 11 Sept
Casale Torricella: Relax in the Woods with Sea View

11. 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 NZ$347
includes taxes & fees
26 Aug - 27 Aug
Villa Montecastello

12. 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 NZ$245
includes taxes & fees
17 Sept - 18 Sept
Residence Arianna

13. 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 NZ$165
includes taxes & fees
28 Aug - 29 Aug
Tuscasì Aparthotel

14. 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 NZ$639
includes taxes & fees
22 Sept - 23 Sept
Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access

15. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is NZ$86
includes taxes & fees
6 Sept - 7 Sept
Sportland

16. 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 NZ$578
includes taxes & fees
21 Sept - 22 Sept
House with pool for 4 pax

17. 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 NZ$251
includes taxes & fees
2 Sept - 3 Sept
Casa di Campagna in Toscana

18. 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 traveller
The price is NZ$694
includes taxes & fees
4 Sept - 5 Sept
Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning

19. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (111 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is NZ$260
includes taxes & fees
26 Aug - 27 Aug
Palazzo al Torrione 2

20. 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 NZ$213
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini
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

Find out more about Montecastelli

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Montecastelli holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Montecastelli. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Montecastelli. Seeing all the best attractions is bound to make you fall in love with Montecastelli. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Montecastelli short-term rentals, that won’t be hard to do.

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.

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

Holiday house with private pool and fenced garden: This holiday home rental outside of Montecastelli is located on a river, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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

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.