Montecastelli Holiday Rentals

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Our top choices for Montecastelli holiday rentals

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (30 reviews)
"The view was so incredible and the pool just like a dream. "
Canada
Sarah
The price is NZ$420
includes taxes & fees
27 May - 28 May
Riserva di Fizzano Residence

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$142
includes taxes & fees
29 May - 30 May
Residence Il Paradiso

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is NZ$230
includes taxes & fees
24 May - 25 May
Casa di Campagna in Toscana

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is NZ$394
includes taxes & fees
3 June - 4 June
Villa Montecastello

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$197
includes taxes & fees
3 June - 4 June
Tuscasì Aparthotel

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$192
includes taxes & fees
25 May - 26 May
Il Pozzo di Sant'Andrea

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$335
includes taxes & fees
24 May - 25 May
Antico Borgo Poggiarello

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$294
includes taxes & fees
30 May - 31 May
Borgo Il Poggiaccio

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 NZ$287
includes taxes & fees
3 June - 4 June
Antico Borgo il Cardino

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is NZ$98
includes taxes & fees
21 June - 22 June
Sportland

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 NZ$285
includes taxes & fees
28 May - 29 May
B&B Palazzo Tortoli

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$284
includes taxes & fees
4 June - 5 June
Palazzo Pacini

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 NZ$154
includes taxes & fees
3 June - 4 June
Hotel Campo Di Carlo

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$719
includes taxes & fees
5 June - 6 June
La Lunaria di Lajatico

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 NZ$170
includes taxes & fees
21 June - 22 June
Beatabb

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$222
includes taxes & fees
5 June - 6 June
Antica Fonte Residenza di Siena

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (51 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is NZ$194
includes taxes & fees
25 May - 26 May
Fullino Nero

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (339 reviews)
"Great stay highly recommend!!"
United States
jon
The price is NZ$174
includes taxes & fees
3 June - 4 June
ApartHotel Anghel

Residence Borgo San Lorenzo a Linari

Residence 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$374
includes taxes & fees
4 June - 5 June
Residence Borgo San Lorenzo a Linari

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is NZ$264
includes taxes & fees
2 June - 3 June
Palazzo al Torrione 2
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$110 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?

Holiday house with private pool and fenced garden: This holiday home rental outside of Montecastelli is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Montecastelli?

Expedia has 15 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 Le Biancane. 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.