Casamaggiore Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Casamaggiore vacation rentals

Seasonal outdoor pool, an infinity pool, pool umbrellas, sun loungers
FonteLiving

FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (5)
"Comfortable apartment in quiet block. Nicely furnished excellent housekeeping nice spacious bathrooms great view from the terrace."
United Kingdom
R
The price is ￥11,773
￥13,318 total
includes taxes & fees
Jan 5 - Jan 6, 2026
FonteLiving
Pillowtop beds, minibar, in-room safe, individually decorated
La Locanda Di Cetona

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.2 out of 10, Wonderful, (5)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona
Bar (on property)
La Piccola Locanda

La Piccola Locanda

La Piccola Locanda
Chiusi
8.8 out of 10, Excellent, (8)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda
View from room
Abbadia Sicille Relais

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥10,525
￥12,129 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Abbadia Sicille Relais
Exterior
Meublé Il Riccio

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Exterior
L'Antica Sosta

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3)
"Molto accoglienti e gentili "
Italy
Valentina
The price is ￥10,709
￥11,780 total
includes taxes & fees
Jan 8 - Jan 9, 2026
L'Antica Sosta
Property grounds
Artisti del Cavallo Tourism

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
The price is ￥12,542
￥14,164 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Artisti del Cavallo Tourism
Camera Superior, vista città, primo piano senza ascensore | Laptop workspace, iron/ironing board, free WiFi
TuscanyLettings Studio&Room

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (1)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is ￥14,577
￥16,770 total
includes taxes & fees
Jan 9 - Jan 10, 2026
TuscanyLettings Studio&Room
Property grounds
Farmhouse in a medieval village between Umbria and Tuscany

Farmhouse in a medieval village between Umbria and Tuscany

Farmhouse in a medieval village between Umbria and Tuscany
Casaltondo
9.0 out of 10, Wonderful, (2)
"This apartment is located in a calm and charming little village, a good starting point to discover Umbria. The 3 bedrooms and 2 bathrooms make the place ideal for a family's comfortable stay. The apartment is well-equipped but we missed the air conditioning in the hot summer days and a microwave for easy cooking. The host were very nice and friendly. We can recommend this apartment for everyone who prefers a calm holiday."
United States
Edit K.
The price is ￥9,199
￥19,870 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Farmhouse in a medieval village between Umbria and Tuscany
Property grounds
Apartment in farmhouse from the late 1800s, in the vicinity of Perugia

Apartment in farmhouse from the late 1800s, in the vicinity of Perugia

Apartment in farmhouse from the late 1800s, in the vicinity of Perugia
Umbria
9.6 out of 10, Exceptional, (5)
"struttura moderna, pulita e completa di tutto"
United States
Mariano S.
The price is ￥9,935
￥15,454 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Apartment in farmhouse from the late 1800s, in the vicinity of Perugia
Deluxe Double Room | View from room
Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Suite Bernardo, Panoramica al terzo piano senza ascensore | 1 bedroom, desk, laptop workspace, iron/ironing board
PienzaLettings Suites

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is ￥13,386
￥15,461 total
includes taxes & fees
Jan 6 - Jan 7, 2026
PienzaLettings Suites
Casa Gioia, vista città, 2 piano senza ascensore | Private kitchen | Fridge, microwave, stovetop, electric kettle
Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
The price is ￥13,548
￥15,639 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Casa Gioia - Casa Olivieri
Lobby
Residenza Fabroni

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ￥13,749
￥15,862 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Residenza Fabroni
Outdoor pool
Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia
La Valle
9.6 out of 10, Exceptional, (7)
"excellent stay. Beautiful pool, well equipped kitchen, very friendly host.Perfect for the visit of the surrondigns: Perugia, the lake, Montepulciano."
United States
cinzia c.
The price is ￥17,882
￥30,576 total
includes taxes & fees
Dec 29 - Dec 30
Villa Graziella, Romantic Perugia
Pool
Loft with flowered courtyard in Val d'Orcia Radicofani

Loft with flowered courtyard in Val d'Orcia Radicofani

Loft with flowered courtyard in Val d'Orcia Radicofani
Radicofani
10.0 out of 10, Exceptional, (1)
"Posto delizioso, curatissimo, ben arredato e ben pulito.Ringraziamo Barbara per la calorosa accoglienza."
Italy
Alessia R.
The price is ￥14,100
￥21,841 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Loft with flowered courtyard in Val d'Orcia Radicofani
Free daily cooked-to-order breakfast
San Michele al Borgo

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ￥18,618
￥21,216 total
includes taxes & fees
Jan 27 - Jan 28, 2026
San Michele al Borgo
Exterior
Montecchio di Cortona

Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is ￥11,039
￥14,351 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Montecchio di Cortona
Property grounds
Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥12,878
￥16,926 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Holiday home with panoramic terrace ideal for families and couples
Outdoor dining
Medieval village TOP flat, third floor with Wi-Fi & aircon

Medieval village TOP flat, third floor with Wi-Fi & aircon

Medieval village TOP flat, third floor with Wi-Fi & aircon
Compignano
10.0 out of 10, Exceptional, (3)
"Appartamento curatissimo inserito in borgo medievale a soli 20 minuti da Perugia, ideale per vacanza di relax ma vicinissimo a tutto. Soggiorno fantastico, ci tornerò!"
Italy
Marras
Medieval village TOP flat, third floor with Wi-Fi & aircon
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 9 days ago
Monastero di Cortona Hotel & Spa

Find out more about Casamaggiore

Search for holiday rentals in Casamaggiore on Expedia! You can easily find your home rentals, villas, holiday apartments in Casamaggiore using one of the methods below:

  • View our selection of featured holiday rentals in Casamaggiore
  • Use the map to find apartments and other holiday homes in the Casamaggiore neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Casamaggiore while they last

Look no further and take a look at our great range of rental properties in Casamaggiore!

Frequently asked questions

Can I find vacation rentals in Casamaggiore?

Yes, we give you a choice of vacation rentals close to top local attractions in Casamaggiore, or you can choose a secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Casamaggiore?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: You might want to consider this vacation home rental near Casamaggiore, which is located in the city center and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals will I find in Casamaggiore?

With 3 Expedia vacation rentals, you're sure 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 Naturalistic Oasis La Valle, or get out into nature at a spot like Chiusi Lake. La Braccesca Winery and Rocca del Leone are a couple of places you'll find in the larger area.

What’s a vacation rental in Casamaggiore like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Casamaggiore. Vacation rentals offer extras such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for families.