Montecastelli Vacation Rentals

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Sep 1 - Sep 2
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Vacation Rentals in Montecastelli

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

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
ApartHotel Anghel
Lobby lounge

ApartHotel Anghel

8.4 out of 10, Very Good, (324)
"Hotel is close to Siena and the check-in person (Gabriela) was very friendly and helpful. Room is spacious, functional with easy parking in front of the building and just a 3 minute drive to garage in Siena old-town so very convenient to visit this beautiful city. Excellent value for the money."
The price is ￥14,902
￥17,079 total
includes taxes & fees
Sep 3 - Sep 4
ApartHotel Anghel
Camping Boschetto Di Piemma
2 bars/lounges

Camping Boschetto Di Piemma

3.0 star property
8.8 out of 10, Excellent, (82)
"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."
Camping Boschetto Di Piemma
Tuscasì Aparthotel
Royal Apartment | View from room

Tuscasì Aparthotel

9.2 out of 10, Wonderful, (19)
"Very clean and comfortable accommodations. Beautiful view of the countryside!"
The price is ￥11,843
￥13,542 total
includes taxes & fees
Sep 25 - Sep 26
Tuscasì Aparthotel
agriturismo la roggiola
Banquet hall

agriturismo la roggiola

9.6 out of 10, Exceptional, (108)
"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
Outdoor dining

Villa with large garden in the Chianti hills

9.6 out of 10, Exceptional, (72)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
The price is ￥17,183
￥20,276 total
includes taxes & fees
Sep 15 - Sep 16
Villa with large garden in the Chianti hills
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Outdoor pool

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

10.0 out of 10, Exceptional, (98)
"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
Holiday house with private pool and fenced garden
A heated pool

Holiday house with private pool and fenced garden

10.0 out of 10, Exceptional, (59)
"Wonderful hosts, perfect location, comfortable and beautiful villa with lovely heated swimming pool and all amenities for all ages."
Holiday house with private pool and fenced garden
Palazzo Pacini
Property entrance

Palazzo Pacini

9.8 out of 10, Exceptional, (94)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
The price is ￥22,296
￥24,869 total
includes taxes & fees
Sep 30 - Oct 1
Palazzo Pacini
panoramica casa con piscina privata
Pool

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 ￥13,918
￥25,774 total
includes taxes & fees
Sep 8 - Sep 9
panoramica casa con piscina privata
La Casa di Ines
Exterior detail

La Casa di Ines

10.0 out of 10, Exceptional, (1)
The price is ￥10,825
￥12,766 total
includes taxes & fees
Sep 25 - Sep 26
La Casa di Ines
Country House & Spa - Inside Nature with panoramic views, Art Surrounded
Terrace/patio

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

9.8 out of 10, Exceptional, (62)
"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
Residence Il Paradiso
Property entrance

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 ￥8,351
￥9,186 total
includes taxes & fees
Oct 1 - Oct 2
Residence Il Paradiso
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Outdoor pool, an infinity pool

Beautiful apartment in San Gimignano - RoccaiaCasa'70

9.8 out of 10, Exceptional, (43)
"Quiet place to stay"
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Riserva di Fizzano Residence
Outdoor pool, pool umbrellas, sun loungers

Riserva di Fizzano Residence

3.0 star property
9.8 out of 10, Exceptional, (20)
"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 ￥34,725
￥38,542 total
includes taxes & fees
Sep 5 - Sep 6
Riserva di Fizzano Residence
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Outdoor pool

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (109)
"We had a lovely stay at the villa. The villa was comfortable, well furnished and had a beautiful view of San Gimignano. The owner was very helpful and responsive. We will definitely stay there again if we visit San Gimignano."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Le Macine, a wonderful ancient restored watermill with Pool
Pool

Le Macine, a wonderful ancient restored watermill with Pool

9.6 out of 10, Exceptional, (79)
"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
Villa for groups and families, with Private Pool in Monteverdi Marittimo
Outdoor pool

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.
Property grounds

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (66)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
Outdoor pool

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.

10.0 out of 10, Exceptional, (117)
"Great place to stay with family/friends. The grounds are beautiful and immaculately maintained. The house is spotless. The owners organized a meal and a cooking class at the villa for us. They were willing and able to help in any way possible and were very organized with the check in and check out process. Will definitely return. "
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
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

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
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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 Alta Val d'Elsa River Park. 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.