Montecastelli Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Montecastelli vacation rentals

Apartment in Montecastelli Pisano

Legible Butterfly
$594 nightly
The price is $597
Mar 14 - Mar 15
Total with taxes and fees
Legible Butterfly

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

Townhouse in Sovicille

Casa di Campagna in Toscana
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
Casa di Campagna in Toscana

Townhouse in Siena

Il Pozzo di Sant'Andrea
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea

Residence in Casole d'Elsa

Tenuta Cantona
Tenuta Cantona

Villa in Lajatico

La Lunaria di Lajatico
$177 nightly
The price is $199
Apr 1 - Apr 2
Total with taxes and fees
La Lunaria di Lajatico

Residence in Guardistallo

Residence Il Paradiso
3.0 star property
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
$81 nightly
The price is $89
Apr 7 - Apr 8
Total with taxes and fees
Residence Il Paradiso

Aparthotel in San Gimignano City Centre

La Casa di Ines
9.6 out of 10, Exceptional, (8 reviews)
"Love this town. Location is great "
United States
William
$76 nightly
The price is $90
Mar 16 - Mar 17
Total with taxes and fees
La Casa di Ines

Aparthotel in Sovicille

Tuscasì Aparthotel
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
$71 nightly
The price is $82
Mar 15 - Mar 16
Total with taxes and fees
Tuscasì Aparthotel

Residence in Monteriggioni

Antico Borgo Poggiarello
2.0 star property
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
$242 nightly
The price is $270
Mar 27 - Mar 28
Total with taxes and fees
Antico Borgo Poggiarello

Aparthotel in Guardistallo

Beatabb
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
Beatabb

Townhouse in San Gimignano City Centre

B&B Palazzo Tortoli
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
$140 nightly
The price is $160
Mar 21 - Mar 22
Total with taxes and fees
B&B Palazzo Tortoli
$2,613 nightly
The price is $2,616
Apr 7 - Apr 8
Total with taxes and fees
Apartment "Tenuta Acquabona - Entire Country House" with Pool
10.0 out of 10, Exceptional, (57 reviews)
"Amazing property and design origin - it brought even more value and joy to our stay. Spacious family room with spectacular morning views. Fully functional kitchen for our own home cooked Italian meal!"
United States
Todd J.
$449 nightly
The price is $449
Mar 25 - Mar 26
Total with taxes and fees
Prestigious apartment infinity pool breathtaking view wifi and air conditioning
10.0 out of 10, Exceptional, (1 review)
"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.
$899 nightly
The price is $899
Mar 16 - Mar 17
Total with taxes and fees
Holiday Home 'Podere Le Rote' with Private Pool, Private Garden and Wi-Fi

Villa in Monteriggioni

Villa Montecastello
$170 nightly
The price is $190
Apr 3 - Apr 4
Total with taxes and fees
Villa Montecastello

Residence in Colle di Val d'Elsa

Palazzo Pacini
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
$152 nightly
The price is $170
Mar 21 - Mar 22
Total with taxes and fees
Palazzo Pacini
9.8 out of 10, Exceptional, (59 reviews)
"Excellent home and location. Would highly recommend!!"
United States
Vincent S.
$458 nightly
The price is $458
Mar 14 - Mar 15
Total with taxes and fees
Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning
$803 nightly
The price is $807
Mar 31 - Apr 1
Total with taxes and fees
'La Ripa - Apartment Il Fienile' with Shared Pool & Wi-Fi
$159 nightly
The price is $162
Mar 15 - Mar 16
Total with taxes and fees
Apartment 'Leonardo' with Private Terrace, Wi-Fi and Air Conditioning
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Montecastelli Hotel Reviews

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 $82 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?

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

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 Sentierelsa Trail. In the larger area, you’ll find Medici Fortress and Etruscan Museum.

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.