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Montecastelli Vacation Rentals

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Our top choices for Montecastelli vacation rentals

Residence Il Paradiso

Residence Il Paradiso
3.0 star property
Guardistallo
8.4 out of 10, Very good, (26 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 CA $131
CA $144 total
includes taxes & fees
Jul 8 - Jul 9
Residence Il Paradiso

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (28 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is CA $116
CA $148 total
includes taxes & fees
Jul 12 - Jul 13
Tuscasì Aparthotel

Villa Mucellena

Villa Mucellena
Casole d'Elsa
Villa Mucellena

Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (4 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 CA $192
CA $217 total
includes taxes & fees
Jul 6 - Jul 7
Residence Arianna

Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 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 CA $258
CA $289 total
includes taxes & fees
Jul 17 - Jul 18
Villa Montecastello

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is CA $157
CA $179 total
includes taxes & fees
Jul 26 - Jul 27
Il Pozzo di Sant'Andrea

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is CA $175
CA $201 total
includes taxes & fees
Aug 1 - Aug 2
Casa Vacanze Le Case

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (83 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is CA $183
CA $209 total
includes taxes & fees
Jul 9 - Jul 10
Antico Borgo il Cardino

Fattoria Podere i Luoghi

Fattoria Podere i Luoghi
Casale Marittimo
The price is CA $110
CA $127 total
includes taxes & fees
Jul 6 - Jul 7
Fattoria Podere i Luoghi

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (53 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is CA $137
CA $158 total
includes taxes & fees
Jul 16 - Jul 17
Fullino Nero

Detached house with garden a few minutes from the abbey of San Galgano

Detached house with garden a few minutes from the abbey of San Galgano
Toscana
The price is CA $81
CA $197 total
includes taxes & fees
Jul 6 - Jul 7
Detached house with garden a few minutes from the abbey of San Galgano

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is CA $153
CA $176 total
includes taxes & fees
Jul 16 - Jul 17
Palazzo al Torrione 2

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (33 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is CA $351
CA $390 total
includes taxes & fees
Jul 10 - Jul 11
Riserva di Fizzano Residence

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is CA $217
CA $241 total
includes taxes & fees
Jul 8 - Jul 9
Palazzo Pacini

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is CA $191
CA $215 total
includes taxes & fees
Jul 7 - Jul 8
Casa di Campagna in Toscana

Podere Cagnesi: Relaxation in nature

Podere Cagnesi: Relaxation in nature
Podere Cagnesi
The price is CA $187
CA $345 total
includes taxes & fees
Jul 6 - Jul 7
Podere Cagnesi: Relaxation in nature

Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is CA $172
CA $198 total
includes taxes & fees
Jul 16 - Jul 17
Materia Rooms San Gimignano

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is CA $70
CA $81 total
includes taxes & fees
Jul 19 - Jul 20
Sportland

La Lunaria di Lajatico

La Lunaria di Lajatico
Lajatico
10.0 out of 10, Exceptional, (1 review)
"Umwerfend schöne Aussicht! Charmantes Dorf. Ruhige Lage. "
United Kingdom
Julia
The price is CA $457
CA $604 total
includes taxes & fees
Jul 12 - Jul 13
La Lunaria di Lajatico

Beatabb

Beatabb
Guardistallo
9.2 out of 10, Wonderful, (9 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 CA $147
CA $162 total
includes taxes & fees
Jul 7 - Jul 8
Beatabb
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

Beautiful stone house with garden and private pool.: This vacation home rental outside of Montecastelli is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

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 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.