Montecastelli Vacation Rentals

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Vacation Rentals in Montecastelli

Apartment in Siena

8.4 out of 10, Very Good, (331)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
ApartHotel Anghel

Camping in San Gimignano

3.0 star property
8.8 out of 10, Excellent, (85)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma

Vacation Home in Siena

9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills

Aparthotel in Sovicille

9.0 out of 10, Wonderful, (24)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$58 nightly
The price is $68
Nov 20 - Nov 21
Total with taxes and fees
Tuscasì Aparthotel

Cottage in Monticiano

9.6 out of 10, Exceptional, (112)
"A Nice Home in nature with a lot of animals."
Germany
Tabea S.
agriturismo la roggiola

Villa in Casale marittimo

9.0 out of 10, Wonderful, (6)
"Perfetta e rilassante. Posto splendido anche per i nostri cani che sono stati benissimo. Corrado sempre presente e disponibile per tutte le nostre necessità. Una meraviglia. "
Italy
Caterina C.
Extra privacy, Dog friend, Special Children, Unspoiled nature, Sea

Villa in San Gimignano

10.0 out of 10, Exceptional, (106)
"Great villa in a lovely location. We (8 adults and 2 children) really enjoyed our trip. It had everything we needed and a beautiful view from the pool! Thank you to Allesandro for helping us book things in the local area too. "
United Kingdom
Catherine T.
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

Villa in Belforte

10.0 out of 10, Exceptional, (78)
"What an awesome place. Lovely house and backyard with pool. Leo is friendly , helpful and welcoming . Belforte is a small , quiet hilltop village but it is very accessible (by car) to other awesome spots- Siena, San Gimignano , Volterra and others. Highly recommended "
New Zealand
Adrian d.
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool

Vacation Home in Boccheggiano

9.6 out of 10, Exceptional, (56)
"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."
United Kingdom
Patrick H.
Private House with Exclusive Swimming Pool Heated and Amazing View

Apartment in San Gimignano City Centre

9.6 out of 10, Exceptional, (36)
"Great experience in a medieval villa converted to apartments. We were there for one night and enjoyed it very much!"
United States
Matthew E.
$171 nightly
The price is $177
Dec 2 - Dec 3
Total with taxes and fees
san gimignano apartment in historical center, courtyard and fast free wifi

Vacation Home in Volterra

10.0 out of 10, Exceptional, (63)
"it was a great holiday, with a beautiful house, beautiful view and a very friendly welcome from Jurgen."
Netherlands
frank l.
Holiday house with private pool and fenced garden

Vacation Home in Volterra

9.6 out of 10, Exceptional, (82)
"A lovely stay, good quality air con in bedrooms, Alex is a great host. Make sure you go to one of the meals he hosts because the food was divine. Good location to Volterra, property is right next to a road but gated. "
United Kingdom
Anna W.
Le Macine, a wonderful ancient restored watermill with Pool

Villa in siena

7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
$174 nightly
The price is $174
Dec 1 - Dec 2
Total with taxes and fees
panoramica casa con piscina privata

Villa in Siena

10.0 out of 10, Exceptional, (107)
"We had a wonderful time visiting Siena and other towns within a one hour drive.The service from Simone and Francesca was outstanding. The pool was great and helped entertain our 7 year old grandson. Would definitely stay again!!!"
United States
David and Susan W.
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Vacation Home in Volterra

9.8 out of 10, Exceptional, (65)
"Villanovia is as wonderful as it looks online. Marco and Laura are exceptional hosts and took care of us with kindness and made sure our every need was well taken care - we had a lovely stay! Thank you Marco and Laura!"
United States
Sarah R.
Country House & Spa - Inside Nature with panoramic views, Art Surrounded

Apartment in San Gimignano

9.8 out of 10, Exceptional, (48)
"We really enjoyed our stay. It was in a very quiet, out of the way picturesque place. Our host was great - had everything we needed and very helpful and great communication. Would definitely recommend and would stay here again. "
Canada
Danielle H.
Beautiful apartment in San Gimignano - RoccaiaCasa'70

Vacation Home in Monteverdi Marittimo

9.0 out of 10, Wonderful, (2)
"Appartamento ben arredato con grande terrazza e vista magnifica sulle colline. Ho apprezzato molto cenare fuori alla luce della luna piena e approfittare sin dal mattino della bella atmosfera. La piscina è molto vicina e Gina è stata fantastica ad accoglierci e darci consigli dall'inizio alla fine del nostro soggiorno. Grazie e a presto! "
Italy
Ilaria
Watching The Horizon in residence with swimming pool for a fee

Aparthotel in San Gimignano City Centre

9.4 out of 10, Exceptional, (6)
"Love this town. Location is great "
United States
William
$85 nightly
The price is $100
Dec 19 - Dec 20
Total with taxes and fees
La Casa di Ines

Residence in Castellina in Chianti

3.0 star property
9.8 out of 10, Exceptional, (23)
"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
Riserva di Fizzano Residence

Vacation Home in Siena

10.0 out of 10, Exceptional, (27)
"Great value for the area! The photos reflect the property accurately. The outdoor areas are spectacular including the patio and pool area. Simone and Francesca were helpful throughout the process with quick answers and great recommendations. "
United States
Lane R.
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
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 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 $68 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?

Casa Vacanze Le Case: This vacation home rental outside Montecastelli offers an outdoor pool, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a stovetop and kitchenware can make your vacation run smoothly. You and your friends and family can relax into your vacation with amenities like a garden.

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.