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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Montecastelli holiday rentals

Terrace/patio

Townhouse in Sovicille

Casa di Campagna in Toscana
9.4 out of 10, Exceptional, (21 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
Casa di Campagna in Toscana
Reception

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Exterior

Townhouse in Siena

Il Pozzo di Sant'Andrea
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea
La casa di Jakin | Terrace/patio

Residence in Casole d'Elsa

Tenuta Cantona
The price is ฿3,623
฿6,112 total
includes taxes & fees
1 Apr - 2 Apr
Tenuta Cantona
Apartment, 1 Bedroom, Ground Floor (Garden) | Exterior

Residence in Guardistallo

Residence Il Paradiso
3.0 star property
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 ฿2,842
฿3,312 total
includes taxes & fees
28 Mar - 29 Mar
Residence Il Paradiso
2 outdoor pools, pool umbrellas, pool loungers

Villa in Lajatico

La Lunaria di Lajatico
The price is ฿3,267
฿5,907 total
includes taxes & fees
23 Mar - 24 Mar
La Lunaria di Lajatico
Premium bedding, down duvets, pillow-top beds, minibar

Aparthotel in Sovicille

Tuscasì Aparthotel
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 ฿2,225
฿2,932 total
includes taxes & fees
27 Mar - 28 Mar
Tuscasì Aparthotel
Exterior detail

Aparthotel in San Gimignano City Centre

La Casa di Ines
9.0 out of 10, Wonderful, (9 reviews)
"Love this town. Location is great "
United States
William
The price is ฿2,744
฿3,205 total
includes taxes & fees
22 Mar - 23 Mar
La Casa di Ines
Food court

Residence in Monteriggioni

Antico Borgo Poggiarello
2.0 star property
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 ฿8,233
฿9,168 total
includes taxes & fees
27 Mar - 28 Mar
Antico Borgo Poggiarello
Exterior

Apartment in Roccastrada

Country House il Ciliegio
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 ฿2,388
฿2,702 total
includes taxes & fees
18 Apr - 19 Apr
Country House il Ciliegio
Daily self-service breakfast (EUR 6 per person)

Aparthotel in Guardistallo

Beatabb
9.0 out of 10, Wonderful, (8 reviews)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
Beatabb
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

Townhouse in San Gimignano City Centre

B&B Palazzo Tortoli
9.2 out of 10, Wonderful, (61 reviews)
"This is a great B&B its right in the heart of the town. The rooms are very clean and have historical character. The staff are so friendly and helpful. "
United States
April
B&B Palazzo Tortoli
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

Villa Sabolini

Villa Sabolini

10/10 Excellent
"Beautiful Tuscan estate, lovely room, excellent breakfast "
Ariel 2-night trip
Posted 2 days ago
Villa Sabolini

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
  • Use the map to find apartments and other holiday homes in the Montecastelli neighbourhood you prefer
  • 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 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.

How many holiday rentals will I find in Montecastelli?

Expedia has 14 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 Etruscan Museum.

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.