Montecastelli Holiday Rentals

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Holiday Rentals in Montecastelli

Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday

10.0 out of 10, Exceptional, (34)
"We all had a wonderful holiday. The villa was lovely and so well equipped. The garden, hot tub and especially the pool were amazing!! Gina and Franco were so kind to bring us wonderful treats during the stay and left a very generous welcome basket. Absolutely fantastic place for a holiday. We hope to return one day!"
Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday

Camping Boschetto Di Piemma

3.0 star property
8.8 out of 10, Excellent, (84)
"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."
The price is AU$136
includes taxes & fees
15 Oct - 16 Oct
Camping Boschetto Di Piemma

ApartHotel Anghel

8.4 out of 10, Very good, (327)
"Enough space for a family. We were able to walk to restaurants, grocery and old city Siena. "
ApartHotel Anghel

Tuscasì Aparthotel

9.2 out of 10, Wonderful, (21)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
The price is AU$141
includes taxes & fees
1 Oct - 2 Oct
Tuscasì Aparthotel

agriturismo la roggiola

9.6 out of 10, Exceptional, (112)
"Beautiful situation, close to Siena and Orcia valley. Three days very well spent, merci Simonetta !"
agriturismo la roggiola

Villa with large garden in the Chianti hills

9.6 out of 10, Exceptional, (73)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
Villa with large garden in the Chianti hills

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

10.0 out of 10, Exceptional, (101)
"The location and views were absolutely spectacular! Alessandro was EXTREMELY helpful and accommodating. He helped arrange for chef and wine tasting at the villa and they were memorable. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

La Casa di Ines

10.0 out of 10, Exceptional, (2)
"Habitación limpia en buenas condiciones tranquila sin ruido y muy bien ubicada"
The price is AU$139
includes taxes & fees
18 Oct - 19 Oct
La Casa di Ines

Private House with Exclusive Swimming Pool Heated and Amazing View

9.6 out of 10, Exceptional, (53)
"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."
Private House with Exclusive Swimming Pool Heated and Amazing View

panoramica casa con piscina privata

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....
The price is AU$272
includes taxes & fees
6 Oct - 7 Oct
panoramica casa con piscina privata

Residence Il Paradiso

3.0 star property
8.4 out of 10, Very good, (25)
"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!"
The price is AU$142
includes taxes & fees
30 Sept - 1 Oct
Residence Il Paradiso

Riserva di Fizzano Residence

3.0 star property
9.8 out of 10, Exceptional, (22)
"We had 2 beautiful days here in Chianti. Lovely property with a very good restaurant. Stunning views over the vineyards and Tuscany hills. Close drive to interesting cites. And the wine.... love to come back, and can absolutely recomend a stay here."
The price is AU$309
includes taxes & fees
12 Oct - 13 Oct
Riserva di Fizzano Residence

Extra privacy, Dog friend, Special Children, Unspoiled nature, Sea

9.0 out of 10, Wonderful, (6)
"Nonostante il breve periodo di permanenza la struttura era splendida, in un’incantevole scenario di alta collina. Il proprietario estremamente affabile e disponibile per ogni nostra necessità."
Extra privacy, Dog friend, Special Children, Unspoiled nature, Sea

Le Macine, a wonderful ancient restored watermill with Pool

9.6 out of 10, Exceptional, (81)
"House was so cute, owner was there when we arrived and was very responsive to any questions. Great location to many of the surrounding towns."
Le Macine, a wonderful ancient restored watermill with Pool

Country House & Spa - Inside Nature with panoramic views, Art Surrounded

9.8 out of 10, Exceptional, (63)
"We came for the second time to Villanovia and again enjoyed a fabulous week in a unique surrounding. Special thanks to our host Marco!"
Country House & Spa - Inside Nature with panoramic views, Art Surrounded

Holiday house with private pool and fenced garden

10.0 out of 10, Exceptional, (59)
"We had great time. The owners are very accommodating "
Holiday house with private pool and fenced garden

Palazzo Pacini

9.8 out of 10, Exceptional, (96)
"The owners of this hotel are very accommodating. The breakfast was very good. The restaurants around this hotel are plentiful and offer good value and views."
The price is AU$259
includes taxes & fees
30 Sept - 1 Oct
Palazzo Pacini

Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano

10.0 out of 10, Exceptional, (44)
"Great property - well located for interesting day trips."
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano

Villa for groups and families, with Private Pool in Monteverdi Marittimo

8.8 out of 10, Excellent, (12)
"A quiet, idyllic place to relax. We enjoyed it very much"
Villa for groups and families, with Private Pool in Monteverdi Marittimo

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (69)
"The cute little cottage is surrounded by a big garden full of flowers and a nice and cool (not too big) swimmingpool which is in the sun most of the day. It has loads of character and is fully equipped. For me the big bed was a little bit sweaty because of the memory foam. By car lots of Tuscan villages and sites are easily reached. Our hostess mme Tiziana was wonderful and very helpful."
Beautiful stone house with garden and private pool.
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

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 favourite 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 depend 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 AU$136 per night. Entering your travel dates in the search wizard might find you 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?

Country House & Spa - Inside Nature with panoramic views, Art Surrounded: This holiday home rental outside of Montecastelli is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a terrace and a garden so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Montecastelli?

Expedia has 14 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 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.