Casamaggiore Holiday Rentals

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Our top choices for Casamaggiore holiday rentals

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is AU$352
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is AU$125
includes taxes & fees
17 Dec - 18 Dec
Abbadia Sicille Relais
9.6 out of 10, Exceptional, (75)
"Was wonderful and beautiful. "
United States
Alana A.
Farmhouse in the hills with panoramic view and swimming pool

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is AU$388
includes taxes & fees
26 Dec - 27 Dec
Casanova - Panoramic Rooms and Suites

Villa in Sinalunga

Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is AU$306
includes taxes & fees
22 Dec - 23 Dec
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (57)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is AU$160
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza Fabroni

Apartment in Montepulciano

Bellarmino Boutique Apartments
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is AU$172
includes taxes & fees
13 Jan - 14 Jan 2026
Bellarmino Boutique Apartments

Residence in Montepulciano

Il Tosco
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is AU$419
includes taxes & fees
17 Dec - 18 Dec
Il Tosco
9.8 out of 10, Exceptional, (94)
"Lovely home with spectacular views! The home greatly exceeded our expectations. It had everything we needed for our 6 day. When not our touring the charming small Tuscany towns, we enjoyed the peace and quiet of the back porch and pool area. We kept the windows open and enjoyed the sweet breezes blowing through. If you're looking the perfect home to rent in Tuscany, this is the one. "
United States
Teresa G.
Hilltop house in the heart of Tuscany with private pool
10.0 out of 10, Exceptional, (86)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!
10.0 out of 10, Exceptional, (13)
"We had such a lovely week staying in this farmhouse just outside Citta della Pieve. The house itself and interiors are beautiful - the kitchen is well equipped, the beds are incredibly comfortable, the bathrooms modern, the pool is an excellent size, and the views are amazing. The hosts were incredibly friendly and generous, and really added to our overall experience. I would highly recommend a stay here - you will not be disappointed!"
United Kingdom
Clare C.
Country House With Private Pool

Residence in Montepulciano

Osteria del Borgo
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
10.0 out of 10, Exceptional, (60)
"Beautiful property comfortable beds. Amazing views room two sit outside and enjoy sunsets."
United States
Darrel W.
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
10.0 out of 10, Exceptional, (50)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Australia
Belinda P.
Luxury Cortona view hilltop Villa
9.4 out of 10, Exceptional, (22)
"A lovely escape - we enjoyed every moment!"
United States
Anonymous traveller
Villa Casale Silvia Large Private Pool, A/C, WiFi
9.8 out of 10, Exceptional, (47)
"We had a very pleasant stay and enjoyed the house and surroundings to the fullest. The view of the lake is breathtaking.We had very good communication with the owner and bought some of his very good wines."
Denmark
Lars B.
House with garden and panoramic view over Lake Trasimeno
9.8 out of 10, Exceptional, (48)
"We had a wonder stay at the villa. Gave a true Tuscan countryside experience in a luxurious, comfortable and convenient location."
Canada
Ramutis G.
Montalcino Villa - Breathtaking Views of the Val d'Orcia
9.4 out of 10, Exceptional, (46)
"It was amazing!! Great space for 7 adults. Pool area is great. Definitely do a meal with Leonardo. "
United States
Carol W.
Villa with private pool, air conditioning near wineries at 3km from village
8.4 out of 10, Very good, (46)
"We had a great Family Holiday there. We enjoyed the pool so much and the nice terrasse, where we had all our meals and sat in the evenings to watch the Sunset on the lake. We liked the dogs visiting us and Massimo was always helpful."
Germany
Karin
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
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 Casamaggiore Hotel Reviews

Find out more about Casamaggiore

Everything you need to know about Casamaggiore 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 Casamaggiore 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 Casamaggiore holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Casamaggiore holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Casamaggiore. 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 Casamaggiore 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 Casamaggiore holiday rentals we have selected for you start as low as AU$125 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Casamaggiore rentals

At Expedia, we put the best Casamaggiore 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 Casamaggiore 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 Casamaggiore 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 Casamaggiore. 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

Can I find holiday rentals in Casamaggiore?

Yes, there are holiday rentals close to the most popular sights in Casamaggiore, 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 Casamaggiore has to offer?

Farmhouse in the hills with panoramic view and swimming pool: This holiday home rental outside of Casamaggiore is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals will I find in Casamaggiore?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Casamaggiore stay.

What’s there to see and do in Casamaggiore?

Explore the area and family-friendly sights such as Centro Servizi Turistici Citta della Pieve, or get out into nature at a spot like Lake Trasimeno. Rocca del Leone and Val di Chiana are a couple of places you'll find in the wider area.

What’s a holiday rental in Casamaggiore like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Casamaggiore. Holiday rentals provide amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.