Montecastelli Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Montecastelli vacation rentals

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 P6,016
P6,898 total
includes taxes & fees
Apr 8 - Apr 9
Il Pozzo di Sant'Andrea
2 outdoor pools, pool umbrellas, sun loungers

La Lunaria di Lajatico

La Lunaria di Lajatico
Lajatico
The price is P7,497
P12,600 total
includes taxes & fees
Apr 6 - Apr 7
La Lunaria di Lajatico
Terrace/patio

Tenuta Cantona

Tenuta Cantona
Casole d'Elsa
The price is P10,464
P15,513 total
includes taxes & fees
Apr 8 - Apr 9
Tenuta Cantona
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is P10,869
P12,097 total
includes taxes & fees
Apr 11 - Apr 12
Riserva di Fizzano Residence
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 P5,147
P5,662 total
includes taxes & fees
Apr 29 - Apr 30
Residence Il Paradiso
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
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
The price is P6,144
P6,969 total
includes taxes & fees
Apr 8 - Apr 9
Casa di Campagna in Toscana
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 P10,628
P11,902 total
includes taxes & fees
Apr 8 - Apr 9
Antico Borgo Poggiarello
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 P4,597
P5,970 total
includes taxes & fees
Apr 8 - Apr 9
Tuscasì Aparthotel
Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (50 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is P6,671
P7,618 total
includes taxes & fees
Apr 6 - Apr 7
Fullino Nero
Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is P10,336
P11,580 total
includes taxes & fees
Apr 3 - Apr 4
Villa Montecastello
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 P9,350
P15,270 total
includes taxes & fees
Apr 28 - Apr 29
Borgo Il Poggiaccio
Daily self-serve breakfast (EUR 6 per person)

Beatabb

Beatabb
Guardistallo
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
The price is P5,083
P5,591 total
includes taxes & fees
Apr 7 - Apr 8
Beatabb
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 P6,075
P6,823 total
includes taxes & fees
Apr 19 - Apr 20
Palazzo Pacini
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 P5,311
P5,982 total
includes taxes & fees
Apr 18 - Apr 19
Country House il Ciliegio
Exterior

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is P5,124
P5,914 total
includes taxes & fees
Apr 2 - Apr 3
Villa le Camelie Siena
Exterior

Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
The price is P12,767
P14,184 total
includes taxes & fees
Apr 2 - Apr 3
Le Mascie Country House
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 P6,881
P7,920 total
includes taxes & fees
Apr 15 - Apr 16
Antico Borgo il Cardino
Outdoor pool, sun loungers

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 P4,702
P5,312 total
includes taxes & fees
Apr 14 - Apr 15
Hotel Campo Di Carlo
Balcony

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (108 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is P6,591
P9,357 total
includes taxes & fees
Apr 29 - Apr 30
Palazzo al Torrione 2
View from room

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
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
The price is P8,473
P9,668 total
includes taxes & fees
Apr 9 - Apr 10
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

Mormoraia

Mormoraia

10/10 Excellent
"We adored our stay at Mormoraia. The property is lovely, with stunning views of San Gimignano. We enjoyed delicous breakfasts and dinners at the restaraunt. The wait staff was welcoming and attentive (thank you Cristiano!) It was too early in the season to use the infinite pool, but it was gorgeous. I highly recommend. You'll love it here!"
Robin 2-night trip
Posted 5 hours ago
Mormoraia

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:

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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 Alta Val d'Elsa River Park. In the larger area, you’ll find Medici Fortress and Palazzo dei Priori.

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.