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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Montecastelli holiday rentals

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
Garden

Townhouse in Gambassi Terme

Tenuta Quadrifoglio
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is 4.961.834 ₫
5.550.495 ₫ total
includes taxes & fees
26 Feb - 27 Feb
Tenuta Quadrifoglio
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
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 6.811.971 ₫
7.585.676 ₫ total
includes taxes & fees
27 Mar - 28 Mar
Antico Borgo Poggiarello
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 1.587.298 ₫
2.146.897 ₫ total
includes taxes & fees
1 Mar - 2 Mar
Tuscasì Aparthotel
Exterior detail

Aparthotel in San Gimignano City Centre

La Casa di Ines
9.6 out of 10, Exceptional, (8 reviews)
"Love this town. Location is great "
United States
William
The price is 2.037.361 ₫
2.394.800 ₫ total
includes taxes & fees
8 Mar - 9 Mar
La Casa di Ines
Studio, Patio, Ground Floor | Terrace/patio

Cottage in Siena

Fullino Nero
9.6 out of 10, Exceptional, (50 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is 3.688.868 ₫
4.180.717 ₫ total
includes taxes & fees
8 Mar - 9 Mar
Fullino Nero
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
Terrace/patio

Residence in Colle di Val d'Elsa

Palazzo Pacini
9.8 out of 10, Exceptional, (98 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is 3.181.442 ₫
3.561.258 ₫ total
includes taxes & fees
8 Mar - 9 Mar
Palazzo Pacini
Outdoor pool

Holiday Home in San Gimignano

Casa Vacanze Le Case
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is 2.929.428 ₫
3.376.550 ₫ total
includes taxes & fees
26 Feb - 27 Feb
Casa Vacanze Le Case
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 2.343.968 ₫
2.732.222 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Residence Il Paradiso
Reception

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Apartment, 2 Bedrooms, Hill View | Terrace/patio

Residence in Siena

Antica Fonte Residenza di Siena
6.0 out of 10, (2 reviews)
"Not very good hosts. They don’t speak English and they don’t help accomodate guests for issues out of their control. I would stay away very poor customer service "
Australia
Geoffrey
The price is 2.396.580 ₫
2.759.520 ₫ total
includes taxes & fees
27 Feb - 28 Feb
Antica Fonte Residenza di Siena
Balcony

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is 2.327.816 ₫
3.485.710 ₫ total
includes taxes & fees
28 Feb - 1 Mar
Palazzo al Torrione 2
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 1.974.210 ₫
2.233.303 ₫ total
includes taxes & fees
27 Mar - 28 Mar
Country House il Ciliegio
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

10/10 Excellent
"Great one bedroom apartment. Fantastic view ofSan Gimignano from front door. Very peaceful."
Colleen 6-night trip
Posted 9 days ago
Poderi Arcangelo

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 Porta all'Arco.

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.