House vacation 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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Montalcino

5 out of 5 average rating, 114 reviews

Montalcino Townhouse with Private Panoramic Garden & Spa

The perfect holiday retreat! Feel at peace in this home which blends traditional elements with all the modern comforts and some contemporary wall art. Relax in the steam bath and head outside to the panoramic private garden to sink into the Jacuzzi. Enjoy a barbecue or even just a glass of wine under the gazebo, admiring the beautiful view over Montalcino and the surrounding countryside. Whatever you do, you just won't want to leave anymore! A beautiful open plan full of light, with kitchen, sitting area and a bedroom area (king size bed 200x210). The kitchen is equipped with a refrigerator, dishwasher, induction hob, ice machine, wine cellar, Nespresso coffee machine, electric kettle, toaster. The bathroom is equipped with shower, steam bath and sauna with access also from the outside. There is air conditioning, TV with Netflix, wood stove. The large panoramic garden is equipped with a gazebo with table, chairs and barbecue. There are also deckchairs, sun loungers and jacuzzi. All of this will be at your complete and exclusive disposal. I will be more than happy to share with you all my very best suggestions to make your stay here in Montalcino unforgettable :-) The apartment is centrally located in the upper part of Montalcino, only around the corner from the main square. Visit the nearby cathedral before walking to the family-owned restaurants, charming cafes, boutique shops and live like a local. Enjoy local wineries producing the famous Brunello wine, explore the rich history of the region and the beautiful scenic Val d'Orcia - Unesco Heritage Site. The property is located in the limited traffic area. You are allowed to drive very close to the entrance in order to download the luggage. Then I will give you instructions on how to reach the closest free car park , which is located at less than 10 minutes walk from the house. To easily reach Montalcino and to fully appreciate this beautiful area - visiting wineries and discovering the all the true gems of Val d'Orcia - we highly recommend to come by car. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Guest favorite

Home in Poggi del Sasso

4.92 out of 5 average rating, 113 reviews

RESIDENZA LECCIONE

Characteristic country house with exposed wooden beams 2 double bedrooms, 1 bedroom with bunk bed and a double sofa bed in the living room. 2 bathrooms with shower. Large and well-equipped kitchen. Dishwasher, wood-burning oven and electric x espresso machine. Large garden with barbecue, swimming pool and a hot tub. Expenses to be paid on site based on wood consumption €8 per LPG box €6 per cubic meter electricity 0.36 per kw. Wood will be provided for a barbecue and a hot bath in the free hot tub.

Guest favorite

Home in Prato

4.98 out of 5 average rating, 127 reviews

Tofanello Orange Luxury and Modern Comfort 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 pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment, there might still be availability. Turquoise: https://www.airbnb.com/rooms/plus/9430389

Guest favorite

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

Welcome to “Casa di Lyndall” My home is located in the medieval village of Lecchi in Chianti, set in rolling hills, castles, vineyards & olive groves, & provides a view that extends nearly 50 kms. It’s a perfect choice for a family or group of four people. My home is built in typical Tuscan style with exposed chestnut beams, fireplace, and a well appointed kitchen. The 8 metre pool is private & located on the top terrace of the olive grove, has a child proof fence, and 4 sun lounges.

Guest favorite

Home in Cortona

4.95 out of 5 average rating, 127 reviews

LA CASA DE LETIZIA

The house is centrally located and 50 meters from a free park. Equipped with heating, air conditioning, Wi-Fi, 2 TVs, dishwasher, microwave, fridge, washing machine. Linen for home. 80 sqm on two floors over ground floor. With 2 bedrooms, 2 bathrooms, living room and kitchen. There is a baby cot available. Small pets allowed, no smoking. Cortona, historical town, near ArezzoPienza, Montalcino, Montepulciano .. and art cities of Florence, Rome, Perugia, Assisi. At 3 km FS station.

Guest favorite

Home in Greve in Chianti

4.88 out of 5 average rating, 114 reviews

La Meridiana in Montefioralle

In the village of Montefioralle, Meridiana is the charm of historic homes. In front of one of the castle's ancient gates, the house is part of the medieval castle. On the ground floor you will find the kitchen, the dining room with a large fireplace, a sitting area and the old vaulted cellar, on the first floor the two double bedrooms, the bathroom , a living/study and the garden with table and chairs where you can spend pleasant evenings. Free high-speed wifi is available.

Guest favorite

Home in Casamona

4.87 out of 5 average rating, 138 reviews

Stone Cottage in Tuscan Countryside

Old stonehouse, recently restored with all comforts. Immersed in the green of Valdarno hills. Surrounded by a forest with walking path, the house i equipped with modern heating but you will find also a fireplace and an old-time log stove. Perfect as a base for visting the Chianti area. 30 minutes from Florence, Arezzo, Siena. 1h30 from Rapolano Terme Price includes italian breakfast and all the essential (from towels to soap, to shampoo, and so on) WiFi on 4G + Pocket Modem

Guest favorite

Home in Siena

4.98 out of 5 average rating, 120 reviews

[Villa with Park] Free Parking and Wi-Fi

Beautiful villa, nestled in the green hills covered with beautiful olive trees. If your dream is to stay in the beautiful Tuscan hills and wake up in the morning with the singing of birds, thanks to this superlative villa you can do it. It can accommodate up to 7 guests. Its very central yet quiet location, just 10 minutes' drive from the historic center of Siena, and from supermarkets, bars and historic sites, makes it the ideal location for a relaxing stay in Siena.

Superhost

Home in Todi

4.84 out of 5 average rating, 147 reviews

"Palazzaccio Todi Estate" hideaway

from 15th JULY to 31st AUGUST 2025 - Bookings should start on a Saturday and be a minimum of 7 nights or multiples. Nestled in the hills opposite Todi lies our centuries old estate. A 3 bedrooms stone house with fireplace, 18 mt infinity pool, kids' pool and playground, surrounded by 40 hectares of private oak wood and olive orchard. Perfect place for a family holiday, friends get together or couple getaway. We have put our love and sweat to make this place like no other.

Superhost

Home in Monte San Savino

4.82 out of 5 average rating, 188 reviews

In Tuscany between Siena Arezzo, near Chianti

the house is located In Palazzuolo in Monte San Savino, between Siena (30 km ) and Arezzo (30km) the price included the entire house with = 2 double beds + 2 single beds the house is composed of: two bedrooms two bathrooms livingroom kitchen (well equipped ) laundry room big garden parking area the tenant has the exclusive use of the house it s perfect to visit Arezzo and Siena, also Chianti Gargonza Cortona breakfast not included Pet friendly no extracost

Guest favorite

Home in Castellina in Chianti

4.98 out of 5 average rating, 104 reviews

StageROOM03 -Chianti Idillic Country living

This beautiful country house is located in the Borgo di Tuopina, a hamlet overlooking the Chianti hills, only 10 mins drive from Siena and Castellina in Chianti. This original Tuscan country house has been completely renovated in 2019 and boasts 2 bedrooms, 2 bathrooms, TV, a fully equipped kitchen with a dishwasher, two fridges and a washing machine. The outdoor marble hot-tub allows you to fully relax while enjoying the amazing views of the surroundings.

Guest favorite

Home in San Martino Sopr'arno

4.94 out of 5 average rating, 100 reviews

Casa Manu

CARATTERISTICA CASA TOSCANA in pietra immersa nelle colline della provincia di Arezzo. Vicino a Siena, Firenze, Cortona, Perugia, il santuario della Verna con la storia di San Francesco di Assisi, Sansepolcro e i dipinti di Piero Della Francesca. Ideale per trekking, turismo enogastronomico (a pochi km si trovano alcune tra le migliori cantine della Toscana), per appassionati di arte e cultura. Vi accoglieremo con un presente di benvenuto.