Holiday Rentals in Montecastelli

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Montecastelli

Castello di Monterone
Interior
Castello di Monterone
9.8 out of 10, Exceptional, (272)
"Stay here for a truly exceptional castle experience! The property is lovely, the castle is authentic and the restaurant has incredible food!"
The price is €240
includes taxes & fees
6 Oct - 7 Oct
Castello di Monterone
House with garden and panoramic view over Lake Trasimeno
Pool
House with garden and panoramic view over Lake Trasimeno
9.8 out of 10, Exceptional, (43)
"Beautiful location, very handy for the lake (swimming, pedelos etc) and with some lovely restaurants and gelatos in the local town! Views from the property are amazing, it is very quiet and peaceful"
House with garden and panoramic view over Lake Trasimeno
Cortona Umbria / family lake view villa near Tuscany + large salted pool
Outdoor pool
Cortona Umbria / family lake view villa near Tuscany + large salted pool
10.0 out of 10, Exceptional, (88)
"The house and grounds were lovely for our group of 7. Plenty of space to relax after a day of touring the countryside. Barbara was always available to help with any issues."
Cortona Umbria / family lake view villa near Tuscany + large salted pool
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (60)
"Nice location with easy access. Terrace great but only early morning when cool. Missed my air conditioner but fans helped . Plenty of room for 2. Quiet and comfortable."
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Traditional stone cottage in rural, tranquil and quiet location built in 1799
Outdoor pool
Traditional stone cottage in rural, tranquil and quiet location built in 1799
9.8 out of 10, Exceptional, (39)
"John & Dianne were utterly lovely and made every effort for us. The listing is very clear and if you're looking for peace and quiet in a serene valley, you couldn't do better. The track should be driven with care but after the first time accompanied by John, it's not too bad. I wouldn't bring a car with low clearance though. John and Dianne are in their home next door which was nice to know. They very much left us to it and didn't mind us playing our music by the pool. Otherwise we didn't see...
Traditional stone cottage in rural, tranquil and quiet location built in 1799
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (61)
"Firstly, the property was absolutely perfect. It was big, all air conditioned (when it’s so hot outside it needs to be) and really felt like a home from home. All the bedrooms are big and the shutters make it super dark at nighttime for sensitive sleepers. It had everything that we needed and more, with lots of different areas to sit and relax. The pool was beautiful, larger than I was expecting and a great infinity effect as you look over at Cortona. The location was great. Close enough to...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Abbazia San Faustino Residenza d'Epoca
Seasonal outdoor pool, pool umbrellas, pool loungers
Abbazia San Faustino Residenza d'Epoca
7.6 out of 10, Good, (15)
"The hotel is located in a beautiful original old monastery with excellent rooms. The staff is very friendly and professional. The surrounding space is very nice and there is large swimming pool, a must during hot summer days. Dinning is on a very high level, food is excellent and the meals are provided all day. We will definitely come back again in the future. I can sincerely recommend this facility to everyone seeking quiet, peaceful holliday in a beautiful authentic setting in Umbria. "
Abbazia San Faustino Residenza d'Epoca
Farmhouse in the hills with panoramic view and swimming pool
Pool
Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (64)
"We stayed for 10 days recently and had a great time, the house was easy to find and the host answered our queries straight away, he also visited the property every other day to water the plants and check that everything was ok. We had a problem with the dishwasher one day and an electrician turned up within 30 minutes. The photos of the house are true to life and the views from the shaded terrace are amazing. The pool was used almost every day and was cleaned regularly usually early before we...
Farmhouse in the hills with panoramic view and swimming pool
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Outdoor dining
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
10.0 out of 10, Exceptional, (45)
"The property was great for 2 families that needed to spread out. There was a cabinet full of kids toys and a very well equipped kitchen with all you need. The pool was great with a retractable cover that made us feel at ease with our young kids running around. The week we were there it was very hot. The house was hot at night without using air conditioning at night. We only used it during the evenings and the bill at the end of the week was over 600 euro. We also did laundry a few times...
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Villa del Verde, Contemporary House, Perugia
Outdoor pool
Villa del Verde, Contemporary House, Perugia
9.8 out of 10, Exceptional, (52)
"A really well equipped property and fantastic views presented very clean and welcoming Caroline could not be more helpful helping to book a restaurant and a trip plus making us feel at home. Ideal location for touring Umbria "
Villa del Verde, Contemporary House, Perugia
Cottage " I due Pini"
Exterior
Cottage " I due Pini"
10.0 out of 10, Exceptional, (35)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"
NEW!!! Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
Outdoor pool
NEW!!! Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
9.8 out of 10, Exceptional, (26)
"La Fenice was a perfect example of a traditional tuscan hideaway with nothing but hills and trees to gaze upon. The villa was spacious enough for us all - two families or four with kids under 12 and the grandparents! The bedrooms, bathrooms and kitchen were all perfectly clean and comfortable (with aircon in every bedroom which was a welcome relief from the august heat) and the pool area was just beautiful with plenty of seating and grassy areas for the children to play. There are a lot of...
NEW!!! Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
Villa Primula - Holiday Rental in Cortona, Tuscany
Pool
Villa Primula - Holiday Rental in Cortona, Tuscany
9.6 out of 10, Exceptional, (45)
"A great villa for a 3 generation group; lovely pool and garden with plenty of outside furniture. Cafes, shops and transport are within walking distance. Spacious rooms and well equipped kitchen. Owner very helpful."
Villa Primula - Holiday Rental in Cortona, Tuscany
Villa Uccellaia - Country Villa Rental with swimming pool in Umbria
Pool
Villa Uccellaia - Country Villa Rental with swimming pool in Umbria
10.0 out of 10, Exceptional, (61)
"This house is not a "normal" house but with a lot of different rooms. Filled with nice arts and decorated with some old furniture. Real characteristic Italian house. Nice garden with different places to seat. The only comment what I can give is the small kitchen. The garden and the swimming pool is maintained daily. We stayed here with 6 adults ad 4 children. Nice place to be."
Villa Uccellaia - Country Villa Rental with swimming pool in Umbria
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Pool
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
9.4 out of 10, Exceptional, (41)
"Nice enough property, very clean. You need to reconfigure furniture in living room so more people can sit. Ok for 2 people but not really inviting and comfortable. Don't need the dining table in that room or that huge hutch. More wine glasses and bowls needed. Update master bedroom mattress. Very uncomfortable. Grounds very enjoyable! Property manager very responsive and helpful. Not really walkable up to hilltop. Reason for the lower rating is the house is over 200 years old...
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Villa Mulino - Completely renovated old mill in Tuscany
Outdoor spa tub
Villa Mulino - Completely renovated old mill in Tuscany
9.6 out of 10, Exceptional, (5)
"We enjoyed our stay very much. Everything is perfect. The "
Villa Mulino - Completely renovated old mill in Tuscany
Beautiful villa with spectacular views in a rural location
Pool
Beautiful villa with spectacular views in a rural location
9.8 out of 10, Exceptional, (40)
"Fabulous location and property. We had a fantastic family holiday in the house. Great area to explore. Madeline was lovely. We will be back"
Beautiful villa with spectacular views in a rural location
Casa Lina - private pool and garden to enjoy with friends or family
Pool
Casa Lina - private pool and garden to enjoy with friends or family
8.0 out of 10, Very good, (3)
"We had a wonderful stay in this holiday home. It was equipped with air conditioning, which is very handy with the high temperatures in the summer. The best part was the swimming pool, where we could find some refreshments during the heat. It is a wonderful region where you can visit a lot. In less than 10 minutes, you will find 3 supermarkets and the beautiful city of Castiglion Fiorentino. The communication with the owners was not that easy as they only spoke Italian and we did not. But we...
Casa Lina - private pool and garden to enjoy with friends or family
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Outdoor dining
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
9.8 out of 10, Exceptional, (53)
"We spent the summer in Cortona at Il Roseto. Our family of four, plus my mother. It was a dream. The apartment is so lovely and perfectly situated, close to everything, yet tucked away in a quiet spot. The outdoor terrace is filled with roses and fragrant shrubs. Fernando and Pierfrancesco responded quickly to every question or need. Il Roseto was truly our home, and it felt that way. The apartment was recently renovated with new foam mattresses and pillows, and AC mini splits and smart TVs in...
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Heritage Tuscan Farmhouse with private swimming pool
Pool
Heritage Tuscan Farmhouse with private swimming pool
10.0 out of 10, Exceptional, (43)
"We made many lifetime memories in this idyllic, very authentic villa over a terrific week. Louise was extremely helpful in helping us prepare for our stay, and her recommendations for restaurants, wine tastings, and visits around the area were spot on. Best of all was her recommendation to secure a local chef (Elena) to run a 1/2 day cooking class at the villa - an absolute highlight!! Whether it was lazing by the pool or eating amongst the trees in the garden, everything felt exactly as it...
Heritage Tuscan Farmhouse with private swimming pool
Don't see what you're looking for?
See all available properties in Montecastelli
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Montecastelli you may be interested in

Chocohotel
Seasonal outdoor pool
Chocohotel
3.0 star property
8.6 out of 10, Excellent, (445)
"The breakfasts room was spectacular "
The price is €133
includes taxes & fees
1 Oct - 2 Oct
Chocohotel
Borgo Il Melone
Outdoor pool, pool umbrellas
Borgo Il Melone
4.0 star property
8.8 out of 10, Excellent, (275)
"We were initially uncertain about booking here due to some negative online comments; however, very happy we did! it would be difficult to pristinely maintain the property as it is historic and quite large, so if you’re looking for something with every modern amenity, this is not the stay for you. However, the property is a gorgeous setting and the buildings are quaint and charming. Our room was very spacious - a bit of noise transfer through the bathroom. Pool area is beautiful! Great breakfast...
The price is €65
includes taxes & fees
10 Oct - 11 Oct
Borgo Il Melone
La Meridiana Bleisure Hotel
Garden
La Meridiana Bleisure Hotel
4.0 star property
8.4 out of 10, Very good, (301)
"Strange thatva 4* hotel doesn't provide kettle and tea and coffee in the room. No cups, nothing."
The price is €102
includes taxes & fees
6 Oct - 7 Oct
La Meridiana Bleisure Hotel
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.

Frequently asked questions

Can I find a holiday rental 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. Montecastelli is known for its spas and theme park. Make sure you have time to check out the cathedral and coffee shops during your trip.

How many holiday rentals will I find in Monte Castelli?

Expedia has 1133 holiday rentals for your stay in Monte Castelli.

What can I see and do in Montecastelli?

Explore the area and family-friendly sights such as Centro Turistico Sportivo Di Candeleto, or get out into nature at a spot like Tiber River. In the wider area, you’ll find Villa Valentina Resort e Spa and Antognolla Golf.

What’s a holiday rental in Montecastelli like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montecastelli. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.