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Montecastelli Vacation Rentals

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Montecastelli vacation rentals

Pool

1. Peaceful Eco House in the Tuscan hills

Peaceful Eco House in the Tuscan hills
casole d'elsa
$241 nightly
The price is $243
Aug 22 - Aug 23
Total with taxes and fees
Peaceful Eco House in the Tuscan hills
Terrace/patio

2. Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi

Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi
Castelnuovo di Val di Cecina
9.0 out of 10, Wonderful, (2 reviews)
"We had the best time in this beautiful place! The location is absolutely stunning — the garden, house, pool, and everything was perfect and very clean. Tamara is super friendly and kind; she even brought us fresh bread every morning and sold us her delicious honey! Her two dogs are also very sweet and added to the warm, welcoming vibe of the place. The space is very spacious and a truly beautiful corner of nature that you must see.Thank you again, Tamara, for everything!"
Germany
Lea B.
$1,956 nightly
The price is $1,967
Sep 11 - Sep 12
Total with taxes and fees
Holiday Home 'Podere Le Rote' with Private Pool, Garden, and Wi-Fi
Dining

3. Bellavista Farmhouse

Bellavista Farmhouse
Radicondoli
9.0 out of 10, Wonderful, (2 reviews)
"Tutto ok, peccato manca aria condizionata.. ci sono tanti ventilatori.. ma con queste estati torride non bastano più.. zero zanzare .. location bella.. piscina vicinissima e spazio all’aperto privato top."
Italy
Valentina
$566 nightly
The price is $566
Aug 21 - Aug 22
Total with taxes and fees
Bellavista Farmhouse
Outdoor dining

4. 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
$436 nightly
The price is $436
Aug 24 - Aug 25
Total with taxes and fees
Apartment "Radicondoli House" with Balcony & Wi-Fi
Exterior

5. 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
$152 nightly
The price is $173
Sep 3 - Sep 4
Total with taxes and fees
Antico Borgo il Cardino
Family Apartment, 5 Bedrooms, Garden View, Garden Area (10 people) | Terrace/patio

6. 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
$217 nightly
The price is $245
Sep 4 - Sep 5
Total with taxes and fees
Borgo al Cerro
Interior

7. La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!

La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
casole d'elsa siena
10.0 out of 10, Exceptional, (43 reviews)
"We stayed in this beautiful clean, fully airconditioned apartment for 12 days, perfect location for trips to the surrounding area like Siena, Florence, Monteriggioni, Volterra & San Gimignano. The apartment is situated in a peaceful Agriturismo with lots of privacy and a great swimming pool. The owners are really hospitable and you feel welcome right away. Highly recommendable."
Netherlands
Linda T.
$421 nightly
The price is $423
Sep 12 - Sep 13
Total with taxes and fees
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
Property grounds

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

Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
Toscana
$450 nightly
The price is $452
Aug 20 - Aug 21
Total with taxes and fees
Tuscan Private Estate with Pool - 5 Charming Villas at Tenuta Cantona,
Food court

9. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
$144 nightly
The price is $165
Aug 23 - Aug 24
Total with taxes and fees
Borgo Il Poggiaccio
Terrace/patio

10. 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
$113 nightly
The price is $126
Sep 2 - Sep 3
Total with taxes and fees
Palazzo Pacini
Pool

11. Casale Torricella: Relax in the Woods with Sea View

Casale Torricella: Relax in the Woods with Sea View
Montieri
10.0 out of 10, Exceptional, (1 review)
"Pros: Die Lage von Casale Torricella ist traumhaft. Die absolute Ruhe. Man hört lediglich Vogelgezwitscher und trotzdem ist Montieri mit seinem kleinen Supermetcado und 2 empfehlenswerter Lokalen nicht weit entfernt Der unbeschreibliche Duft, der in den Morgenstunden von all den Wildpflanzen ausgeht. Die supernetten Vermieter. Ich könnte stundenlang weiter schwärmen."
Germany
Anonymous traveler
$579 nightly
The price is $579
Sep 10 - Sep 11
Total with taxes and fees
Casale Torricella: Relax in the Woods with Sea View
Outdoor pool

12. 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.
$358 nightly
The price is $360
Sep 9 - Sep 10
Total with taxes and fees
House with pool for 4 pax
Outdoor dining

13. Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning
Colle di Val d'Elsa
10.0 out of 10, Exceptional, (1 review)
"Pros: ***** einfach alles :)"
Germany
Anonymous traveler
$457 nightly
The price is $457
Sep 4 - Sep 5
Total with taxes and fees
Holiday Home 'Rustico Con Jacuzzi In Toscana' with Shared Pool, Wi-Fi and Air Conditioning
Villa, Air conditioning, Courtyard View | Exterior

14. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very Good, (3 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
$192 nightly
The price is $214
Aug 29 - Aug 30
Total with taxes and fees
Villa Montecastello
Seasonal outdoor pool, sun loungers

15. 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
$133 nightly
The price is $150
Sep 16 - Sep 17
Total with taxes and fees
Residence Arianna
Dining

16. Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access

Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
Località Gerfalco Montieri
$358 nightly
The price is $358
Sep 17 - Sep 18
Total with taxes and fees
Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
Terrace/patio

17. 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
$136 nightly
The price is $154
Sep 2 - Sep 3
Total with taxes and fees
Casa di Campagna in Toscana
Premium bedding, down comforters, pillowtop beds, desk

18. 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
$85 nightly
The price is $97
Aug 31 - Sep 1
Total with taxes and fees
Tuscasì Aparthotel
Balcony

19. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (111 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
$133 nightly
The price is $152
Aug 21 - Aug 22
Total with taxes and fees
Palazzo al Torrione 2
Property grounds

20. 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 traveler
$178 nightly
The price is $178
Aug 22 - Aug 23
Total with taxes and fees
Apartment "Casa di Franca a San Galgano" in Historical Centre
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

Hotel Italia

Hotel Italia

10/10 Excellent
"Overall I really enjoyed my stay here. No issues to say the least. I really enjoyed how clean my room was, the staff, breakfast and everything really. I look forward to going back when Im in the area again."
Sean 3-night trip
Posted 2 hours ago
Hotel Italia

Find out more about Montecastelli

Everything you need to know about Montecastelli vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montecastelli vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montecastelli vacation 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 low season months. For more hustle and bustle, you may prefer to visit Montecastelli in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $52 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montecastelli rentals

At Expedia, we put the best Montecastelli vacation 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 vacation.

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 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.

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

Holiday house with private pool and fenced garden: This vacation home rental outside of Montecastelli is located on a river and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Montecastelli?

Expedia has 16 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 Porta all'Arco.

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.