Montecastelli Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Montecastelli vacation rentals

Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (23 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
The price is P7,397
P8,352 total
includes taxes & fees
May 24 - May 25
Casa di Campagna in Toscana
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is P8,610
P9,830 total
includes taxes & fees
May 18 - May 19
Antico Borgo il Cardino
Exterior

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 P6,531
P7,472 total
includes taxes & fees
May 25 - May 26
Il Pozzo di Sant'Andrea
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (30 reviews)
"We loved it!"
United States
Juliette
The price is P12,851
P14,280 total
includes taxes & fees
May 20 - May 21
Riserva di Fizzano Residence
Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is P13,203
P14,738 total
includes taxes & fees
May 18 - May 19
Villa Montecastello
Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P4,310
P5,674 total
includes taxes & fees
May 22 - May 23
Tuscasì Aparthotel
Food court

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 P10,861
P12,162 total
includes taxes & fees
Jun 16 - Jun 17
Antico Borgo Poggiarello
Exterior

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 P5,001
P5,501 total
includes taxes & fees
May 25 - May 26
Residence Il Paradiso
2 outdoor pools, pool umbrellas, sun loungers

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 P18,686
P25,003 total
includes taxes & fees
Jun 5 - Jun 6
La Lunaria di Lajatico
Exterior

Hotel Campo Di Carlo

Hotel Campo Di Carlo
Sassetta
9.6 out of 10, Exceptional, (5 reviews)
"Ci siamo fermati una Notte! Personale gentilissimo tutto perfetto ci ritorneremo fermandoci per più giorni e provare la piscina e le Terme nelle vicinanze"
Italy
antonio
The price is P5,311
P5,986 total
includes taxes & fees
May 18 - May 19
Hotel Campo Di Carlo
Aerial view

Casa La Cedrina Pool Lornano

Casa La Cedrina Pool Lornano
Monteriggioni
Casa La Cedrina Pool Lornano
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is P10,303
P11,692 total
includes taxes & fees
May 18 - May 19
Borgo Il Poggiaccio
Daily self-serve breakfast for a fee

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 P4,866
P5,352 total
includes taxes & fees
May 18 - May 19
Beatabb
Exterior

Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is P4,850
P5,479 total
includes taxes & fees
May 18 - May 19
Country House il Ciliegio
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is P10,181
P11,343 total
includes taxes & fees
May 18 - May 19
Palazzo Pacini
Reception

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is P3,170
P3,631 total
includes taxes & fees
May 24 - May 25
Sportland
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

Hotel Italia

Hotel Italia

8/10 Good
"Basically all good for the price. Breakfast was satisfactory. My four stars more towards the air-conditioning (we are at ground floor so having the window wide opened without any latch is not really an option, we tried variety settings but at the end decided to go with only fans mode), as well as the shower head for our room. Hotel is well located (just take the escalator inside the shopping mall opposite station to go up hill, then turn right), coin laundrette is opposite hotel. Thank you for accommodating us."
Eddy 2-night trip
Posted 3 days ago
Hotel Italia

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.

How many vacation rentals will I find in Montecastelli?

Expedia has 14 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 Le Biancane. In the larger area, you’ll find Medici Fortress and Etruscan Museum.

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.