
House holiday rentals in Cortona
Find and book unique houses on Airbnb
Top-rated house rentals in Cortona
Guests agree: these houses are highly rated for location, cleanliness and more.

Casa Lucy
House located on the Cortonese hill, completely renovated, consisting of 3 double bedrooms, 2 bathrooms and an open space kitchen and dining room. It is located 5 minutes from the historic center of Cortona and in an excellent position to reach the most beautiful and characteristic places of Tuscany and Umbria such as Pienza, Montepulciano, Castiglione del Lago up to cities that are cradles of art such as Florence, Arezzo, Siena and Perugia. Mandatory tourist tax to be paid on site (€2.50 per person for 4 days)

Nonna Nesti Vacation Home
Our vacation home is located in Cortona, a few kilometers from Arezzo, Siena, Perugia, Assisi, Montepulciano and Lake Trasimeno Ideal for food and wine and cultural tours In addition to the large panoramic terrace where you can relax and admire the stars but also dine outdoors, you will be welcomed by a large living room, dining room with fireplace and kitchen as well as two large bedrooms. It will also be pleasant to relax in the large garden where you can spend moments of serenity and tranquility.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

PoggiodoroLoft, Tuscan dream e relax
Welcome to Poggiodoro Loft, 16th century stones' villa located in the countryside of Anghiari. Stunning views, charming and furnished interiors providing all type of comforts: a beautiful fireplace that will keep the ambient warm in winter, the relaxing sauna, the private garden where you can enjoy the open air and lunch under the pergola, BBQ, fantastic in the warm seasons, lounge with brazier a panoramic swimming pool to spend great moments with friends, to be shared with the hamlet guests.

Da nonna Ornella - nest in Val d'Orcia
Spectacular views and relaxation guaranteed in this romantic studio in the heart of Val d 'Orcia, province of Siena, immersed in beautiful Tuscany. Ideal for couples. It has a living area, equipped kitchen, bathroom, heating, private parking and a large and panoramic garden with sun loungers and hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d 'Orcia, Radicofani, Castiglione d 'Orcia, and Monte Amiata. Unforgettable!

Casa Dolce Toscana~Suite&View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation,with panoramic views,immersed in the hills of Tuscany. Anoasis of peace perfect for those who want to relax and live an authentic experience. Located a few kilometers from Siena and Florence,our accommodation combines rustic charm with all modern comforts. it is in the heart of the historic center of the famous village of Cetona,below the castle ,overlooking the valley and the scent of Tuscany.

The Terrace of Victory
La Terrazza di Vittoria is a delightful studio on one level surrounded by silence and greenery. It is located a few meters from the main house and just 2 km from Città della Pieve. The large garden surrounding the house is a natural terrace overlooking Lake Trasimeno. It is enriched by a pergola equipped with a table and barbecue available for your meals in total relaxation. Inside, in a 40 sqm space, there is a double bed, a sofa bed, a bathroom and an equipped kitchen.

La Perla del Lago Holiday home on Lake Trasimeno
Forget all your worries in this oasis of serenity. Let yourself be soothed by our amazing views and the sunsets that the lake offers us every evening La Perla del Lago Holiday Home overlooks Lake Trasimeno. 8 minutes away is the highway from which you can easily reach Florence, Perugia,Gubbio, Spoleto, Norcia and many others In the village there are bars, restaurants, food restaurants, ATM pharmacy,a small playground, 2 km away, a beautiful pool for the hottest days.

House in the Cortona countryside
Formerly a shop in the Cortona village of Fratticciola. The cottage consists of a double bedroom, kitchen and bathroom. Access from the street or internal courtyard. Recent renovation, respecting the tradition and materials of the Valdichiana. You must have a car to reach me and, since I am in a central position, to reach many beautiful villages a few kilometres away such as: Cortona, Arezzo, Montepulciano, Pienza, Siena, Lake Trasimeno, Perugia, Assisi... and others.

Jenny's Barn
The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.

Tofanello Turquoise Luxury with Outdoor Pool
Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Cottage surrounded by nature
"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.
Popular amenities for house rentals in Cortona
House rentals with a pool

La Lisa: country house surrounded by fields

Il Vecchio Mulino

Casa di Lyndall - Entire house with exclusive pool

Luxury Villa with a fantastic view

Country charm walking distance from Cortona centre

Gaiole in Chianti Poggio Casabianca

House Rigomagno Siena

Romantic cosy flat - Toscana Italy
Weekly house rentals

Casaletto di Monsigliolo 3 bedrooms 4 bathrooms

Villa with panoramic lakeview "RenzosOlivengarten"

The small tower

Traditional stone house in Tuscany

the oasis of the foxes

La Casa Tra Gli Ulivi

Casa Bordoli, four beds, three bathrooms

Cortona: a view of the Infinite + free parking
Private house rentals

Family Forest - Pool in the Crete Senesi

Fantastic Apartment in the Heart of Toscana

Lovely home to dream

Casa Isa - Perugia

Noi 2 Vacanze in Fortino d 'Amore

"Hortus Conclusus" House

the birds view

Villa Lake Trasimeno Upper first floor flat 4 p
Destinations to explore
- Piazzale Michelangelo
- Lake Trasimeno
- Lake Bolsena
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Stadio Artemio Franchi
- Tenuta Le Velette
- Basilica of St Francis
- Castiglion del Bosco Winery
- Basilica of Santa Croce
- Teatro Tuscanyhall
- Teatro Verdi
- Furlo Gorge Nature Reserve
- Cantina Colle Ciocco
- Mount Subasio
- Santa Maria della Scala
- Palazzo Pubblico
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Podere Il Cocco




