Montecastelli Holiday Rentals

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Our top choices for Montecastelli holiday rentals

Legible Butterfly

Legible Butterfly
Montecastelli Pisano
The price is NZ$1,047
includes taxes & fees
8 Apr - 9 Apr
Legible Butterfly

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 NZ$187
includes taxes & fees
8 Apr - 9 Apr
Il Pozzo di Sant'Andrea

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 NZ$167
includes taxes & fees
12 Apr - 13 Apr
Casa di Campagna in Toscana

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 NZ$269
includes taxes & fees
12 Apr - 13 Apr
Palazzo al Torrione 2

Tenuta Cantona

Tenuta Cantona
Casole d'Elsa
The price is NZ$410
includes taxes & fees
8 Apr - 9 Apr
Tenuta Cantona

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 NZ$376
includes taxes & fees
27 Apr - 28 Apr
La Lunaria di Lajatico

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 NZ$149
includes taxes & fees
4 May - 5 May
Residence Il Paradiso

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 NZ$200
includes taxes & fees
11 Apr - 12 Apr
Fullino Nero

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 NZ$348
includes taxes & fees
11 Apr - 12 Apr
Riserva di Fizzano Residence

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 NZ$343
includes taxes & fees
7 May - 8 May
Antico Borgo Poggiarello

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 NZ$161
includes taxes & fees
9 Apr - 10 Apr
Beatabb

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is NZ$333
includes taxes & fees
9 Apr - 10 Apr
Villa Montecastello

Apartment 'Leonardo' with Private Terrace, Wi-Fi and Air Conditioning

Apartment 'Leonardo' with Private Terrace, Wi-Fi and Air Conditioning
suvereto
The price is NZ$287
includes taxes & fees
9 Apr - 10 Apr
Apartment 'Leonardo' with Private Terrace, Wi-Fi and Air Conditioning

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 NZ$161
includes taxes & fees
19 Apr - 20 Apr
Tuscasì Aparthotel

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 NZ$410
includes taxes & fees
29 Apr - 30 Apr
Borgo Il Poggiaccio

Borgo San Lorenzo a Linari

Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (98 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is NZ$359
includes taxes & fees
29 Apr - 30 Apr
Borgo San Lorenzo a Linari

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 NZ$189
includes taxes & fees
23 Apr - 24 Apr
Palazzo Pacini

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
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 NZ$198
includes taxes & fees
6 May - 7 May
Casa Vacanze Le Case

Casa Masoni – Your Elegant and Welcoming Home in Tuscany

Casa Masoni – Your Elegant and Welcoming Home in Tuscany
Colle val d'Elsa
9.8 out of 10, Exceptional, (9 reviews)
"Very close from Siena, San Gimignano and Chianti and Colle Val d' Elsa alta a really nice village to visit. 15' walking from the house. Deanna is a perfect anfitriona helping with everything for your stay."
Spain
Jorge S.
The price is NZ$670
includes taxes & fees
17 Apr - 18 Apr
Casa Masoni – Your Elegant and Welcoming Home in Tuscany

Antica Fonte Residenza di Siena

Antica Fonte Residenza di Siena
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 NZ$220
includes taxes & fees
10 Apr - 11 Apr
Antica Fonte Residenza di Siena
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

Everything you need to know about Montecastelli holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montecastelli holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montecastelli holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montecastelli holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montecastelli. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montecastelli holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montecastelli holiday rentals we have selected for you start as low as NZ$161 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montecastelli rentals

At Expedia, we put the best Montecastelli holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montecastelli rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montecastelli holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montecastelli. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best holiday rentals that Montecastelli has to offer?

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

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.