Default HTG hotel image

Montecastelli Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Montecastelli holiday rentals

Pool

1. Peaceful Eco House in the Tuscan hills

Peaceful Eco House in the Tuscan hills
casole d'elsa
The price is HK$1,341
HK$1,902 total
includes taxes & fees
22 Aug - 23 Aug
Peaceful Eco House in the Tuscan hills
Food court

2. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 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 HK$1,272
HK$2,042 total
includes taxes & fees
7 Sept - 8 Sept
Borgo Il Poggiaccio
Terrace/patio

3. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is HK$886
HK$993 total
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini
Exterior

4. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is HK$1,404
HK$1,590 total
includes taxes & fees
3 Sept - 4 Sept
Antico Borgo il Cardino
Terrace/patio

5. Borgo al Cerro

Borgo al Cerro
Casole d'Elsa
9.2 out of 10, Wonderful, (25 reviews)
"Väldigt vackert ställe med bra placering mitt i Toscana. Rummet var väldigt fint, men bilderna från hemsidan var finare, så jag blev lite besviken när vi väl kom in. I övrigt var komplexets omgivningar och trädgård helt fantastisk. Barnen hade roligt med pingisbor och dart och det fanns trevlig grillplats att nyttja. "
Sweden
Frida
The price is HK$1,700
HK$1,916 total
includes taxes & fees
4 Sept - 5 Sept
Borgo al Cerro
Seasonal outdoor pool, pool loungers

6. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (6 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is HK$1,141
HK$1,283 total
includes taxes & fees
11 Sept - 12 Sept
Residence Arianna
Premium bedding, down duvets, pillow-top beds, desk

7. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is HK$638
HK$820 total
includes taxes & fees
17 Aug - 18 Aug
Tuscasì Aparthotel
Exterior

8. Podere Cagnesi: Relaxation in nature

Podere Cagnesi: Relaxation in nature
Podere Cagnesi
The price is HK$1,087
HK$1,994 total
includes taxes & fees
10 Sept - 11 Sept
Podere Cagnesi: Relaxation in nature
Terrace/patio

9. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (25 reviews)
"A wonderful stay. "
United States
Sally
The price is HK$1,067
HK$1,201 total
includes taxes & fees
2 Sept - 3 Sept
Casa di Campagna in Toscana
Exterior

10. Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is HK$1,500
HK$1,677 total
includes taxes & fees
25 Aug - 26 Aug
Villa Montecastello
Outdoor pool

11. House with pool for 4 pax

House with pool for 4 pax
Casole d'Elsa
9.4 out of 10, Exceptional, (3 reviews)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is HK$1,540
HK$2,808 total
includes taxes & fees
10 Sept - 11 Sept
House with pool for 4 pax
Outdoor dining

12. Apartment "Radicondoli House" with Balcony & Wi-Fi

Apartment "Radicondoli House" with Balcony & Wi-Fi
Radicondoli Siena
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful apartment that is well decorated and comfortable with everything you could need Walkable to grocery store and restaurants Parking is free and close by Giovanna was so helpful and excellent communication Can't say enough about this place! "
United States
Corey
The price is HK$2,784
HK$3,612 total
includes taxes & fees
14 Aug - 15 Aug
Apartment "Radicondoli House" with Balcony & Wi-Fi
Property grounds

13. Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,

Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
Toscana
The price is HK$2,446
HK$3,542 total
includes taxes & fees
13 Aug - 14 Aug
Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
Exterior

14. 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 HK$922
HK$1,050 total
includes taxes & fees
1 Sept - 2 Sept
Il Pozzo di Sant'Andrea
Reception

15. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is HK$360
HK$414 total
includes taxes & fees
6 Sept - 7 Sept
Sportland
Front of property – evening/night

16. 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 HK$994
HK$1,138 total
includes taxes & fees
26 Aug - 27 Aug
Residence Borgo San Lorenzo a Linari
Exterior

17. 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 HK$891
HK$980 total
includes taxes & fees
12 Sept - 13 Sept
Residence Il Paradiso
Desk, laptop workspace, free WiFi, bed sheets

18. AlbergoDiffusoVolterra

AlbergoDiffusoVolterra
Volterra
8.6 out of 10, Excellent, (19 reviews)
"Amazing property. Very beautiful "
Canada
Charles
The price is HK$961
HK$1,365 total
includes taxes & fees
26 Aug - 27 Aug
AlbergoDiffusoVolterra
Property grounds

19. Apartment "Casa di Franca a San Galgano" in Historical Centre

Apartment "Casa di Franca a San Galgano" in Historical Centre
CHIUSDINO
10.0 out of 10, Exceptional, (1 review)
"Pros: De ligging"
Netherlands
Anonymous traveller
The price is HK$1,259
HK$1,480 total
includes taxes & fees
9 Sept - 10 Sept
Apartment "Casa di Franca a San Galgano" in Historical Centre
Outdoor pool

20. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is HK$966
HK$1,108 total
includes taxes & fees
28 Aug - 29 Aug
Casa Vacanze Le Case
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montecastelli Hotel Reviews

Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent
"My husband and I fully enjoyed our stay at the Villa Ermellina. We had a room near the gym, spacious and convenient. Much space to move around, a table with 2 chairs and a very large bathroom. Sufficient closet space as well. Dining on the property offers a wonderful terrasse for breakfast or any meal, but meals are pricey. We still greatly enjoyed our choices. The pool area is certainly a big attraction to this wonderfully located property in Sienna. This completed our vacation feel in Tuscany."
Elisabeth 5-night trip
Posted 1 day ago
Villa Ermellina Siena, a Tribute Portfolio Hotel

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.

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 16 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.