Vacation rentals in Le Contesse

4.99 out of 5 average rating, 155 reviews

Cortona’s Rooftop Nest

L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

4.93 out of 5 average rating, 14 reviews

A spacious dining area features a long wooden table surrounded by elegant chairs, with a large chandelier hanging above. Vintage furniture and decor items are showcased in a cabinet, complemented by light streaming through an archway that leads to the kitchen.

Villa in Camucia

Apt. Rolando-Tenuta VillaAugusto

La struttura è ubicata in un agglomerato distante 3/4 km dal centro di Cortona. Circondata dal verde, un vero paradiso di tranquillità. Alloggio indipendente e accogliente con ampi spazi arredati con mobili e oggetti d'epoca, cucina attrezzata, camera da letto, biliardo e sala Pianoforte. Ambienti climatizzati. Spazio esterno attrezzato con tavolo, sedie e lettini. Ampio parco con molti spazi ombreggiati e grande piscina (14x7) immersa nel verde, condivisa con gli altri ospiti della tenuta.

Superhost

A refreshing swimming pool is framed by lush greenery and vibrant flowers. Comfortable lounge chairs are placed on the well-maintained lawn, offering views of the surrounding landscape. The gentle slope leads to olive trees, enhancing the tranquil setting.

Villa in Cortona

4.82 out of 5 average rating, 11 reviews

Idyllic Tuscan villa near Cortona with pool

Villa Le Contesse sleeps 6+1 people in three bedrooms with three bathrooms. It nestles in the immediate out skirts of Cortona, one of the many fabulous villas and stately mansions built in this prosperous part of Tuscany in the preceding centuries. The grounds are extensive, comprising 2 hectares of mature and well-tended garden and parkland with small fountains, niches with classical statuary and overlooks hidden in unexpected places. At guests disposal a pool (9.5 x 4.5, depth 1.30 meters).

4.95 out of 5 average rating, 131 reviews

LETIZIA'S HOUSE

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.

4.98 out of 5 average rating, 170 reviews

The image showcases a view from a window featuring a historic clock tower, adorned with a clock indicating the time. The rooftops of neighboring buildings are visible, emphasizing the charming, rustic architecture of the area.

Condo in Cortona

Chicca: bright and panoramic in the historic center

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

4.94 out of 5 average rating, 259 reviews

Vacation home in Cortona

La casina sulle Mura (with garden and spa jacuzzi)

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

4.85 out of 5 average rating, 110 reviews

A window with green shutters is open, providing a view of rooftops below. The landscape features rolling hills under a clear blue sky. The image captures the architecture of a historic area, with traditional tiled roofs and greenery visible in the distance.

Vacation home in Cortona

La Civetta Deliziosa, a studio apartment in the center

characteristic studio apartment inside a terrace owned by the 1600s. Ceilings with wooden beams and terracotta, parquet on the ground and furnishings typical of Tuscan tradition. Kitchen equipped and equipped with everything you need to have breakfast and cook. It is located on the first level, with convenient access from Via del Giardino. Quiet area and in the heart of the historic center, 150 meters from the free parking lot of Piazzale del Mercado

A narrow, cobblestone street is flanked by historic stone buildings and lush greenery. Towering trees and blooming plants provide a natural ambiance, while a vehicle is parked in the distance. The sky above features a mix of sunlight and clouds, creating a serene outdoor scene.

4.97 out of 5 average rating, 164 reviews

CasaNella: bright, central and panoramic

Cozy, elegant and delightful apartment in the center of Cortona, with an enchanting view that sweeps from Lake Trasimeno to Valdichiana. Carefully furnished, it is the ideal place to spend a few days in this wonderful town. A short walk from the main road, but in a quiet and panoramic location. Free parking is a short distance away. Equipped with heating and air conditioning. High speed WiFi available. Great for smart working.

A view from a window frames a historical stone building, featuring a prominent clock tower. The surrounding rooftops of the city are visible, along with casual gatherings of people below. Red roses are placed in the foreground, adding a touch of color to the scene.

4.94 out of 5 average rating, 202 reviews

Casa del Passerino

Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

A small terrace table is set against a breathtaking view, featuring rooftops of the historic city below and a distant landscape. A tray with a bottle of red wine and two glasses rests atop the round table, inviting relaxation and enjoyment of the scenery.

4.97 out of 5 average rating, 156 reviews

I Terrazzini apt.1

In one of the most beautiful old buildings of the hystorical center, completely refurbished very sunny and scenic: a balcony with a spectacular view over Cortona roofs,Valdichiana, Trasimeno Lake and mountains far away. Living,attic,dinig,kitchen,bathroom,two bedrooms. Just few steps down the street and you are in Ruga Piana or Signorelli Square "movida"

4.97 out of 5 average rating, 102 reviews

Home in Torreone

Tuscany House | View Breathtaking

Casa Belvedere is 10 minute drive from the center of Cortona. Is located along an old Roman road and enjoys a spectacular view of Cortona. Equipped cooking, 2 double room, 2 bathrooms, sofa bed, large garden with provides all the comforts to relax, sunbathe and have lunch under the pergola, enjoying the view of Cortona and the Val di Chiana.

4.96 out of 5 average rating, 362 reviews

Cortona Shabby Chic House (Independent & balcony)

Il mio alloggio è situato in pieno centro storico a soli pochi passi dalle piazze e vie principali. Questo grazioso appartamento è di recente ristrutturazione e può ospitare fino a 3 persone. Appartamento indipendente con entrata singola tutto in un solo piano. Arredato con cura e dotato di tutti i comfort.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Le Contesse vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Le Contesse

4.96 out of 5 average rating, 94 reviews

Casa Lucy

KateRating, 5 stars5 days ago

Casa Lucy has the most fabulous pool. If it’s an important part of your stay, as it was for us, you won’t find better. There are three well-proportioned bedrooms and two excellent shower rooms. Air conditioning is a welcome feature as it was hotter than normal when we visited in early June. The outside seating areas provide flexibility for sunshine or shade at all times of day. The view is fabulous. We thoroughly enjoyed our two weeks. Thank you Valter.

4.75 out of 5 average rating, 4 reviews

Casa Coccinella with view and parking

MarkRating, 5 stars1 month ago

Great location, recently remodeled, well stocked kitchen, and very comfortable. Short walk up 2 escalators to town.

Villa in Cortona

4.63 out of 5 average rating, 38 reviews

Belvilla by OYO Villa Nigra

EmeraldRating, 5 stars1 month ago

Absolutely loved our stay at Villa Nigra! It was an amazing house and location with incredible views. Luca was very responsive and helpful with a great attitude. The view makes the whole stay worth it, however the walk up/down the hill is very steep! Communication is better using Luc’a phone number during the stay, not the airbnb app but he was very efficient with anything we needed. My family and I felt very at home in the beautiful house and enjoyed our time in Cortona, thank you Luca!

Farm stay in Cortona

5 out of 5 average rating, 19 reviews

Villa in Cortona , large garden, pool with a view

KatyRating, 5 stars2 weeks ago

We stayed at Andrea’s place for a fortnight in May, and it was stunning! Beautiful grounds - very private and an oasis of flowers, nature and seating areas with a stunning pool! The 3 apartments layout worked brilliantly for us and all were furnished to a high standard with great amenities. Andrea as a host is so helpful too! He helped arrange private drivers so we could go wine tasting and sent taxi numbers to us. The location is stunning - at the foot of the hill of cortona, a medieval walled town that’s so gorgeous & charming! Camucia is closer and you can walk there in <15mins but it’s not as pretty as cortona. Station in camucia is a direct train into Florence which was great for a day trip. The only thing I would say is that walking to cortona is very steep & tricky - much much easier to drive in 5mins and plenty of parking too which is good. Overall though, we loved our time here and would recommend in a heartbeat!

4.97 out of 5 average rating, 137 reviews

Condo in Cortona

Casa Clara Cortona Cin IT051017c28a6h9glv

NeydaRating, 5 stars3 days ago

I absolutely loved this place. It was cozy and charming located in the perfect spot in Cortona. Clara was so friendly despite her only speaking in Italian, she made sure to greet me and communicate everything with me. She also gave me a lot of recommendations and was very responsive. Would stay here again!

4.97 out of 5 average rating, 95 reviews

A restored Tuscan farmhouse is presented in this image, showcasing a blend of stone and brick exterior. Potted plants and a gravel area surround the entrance, while wooden shutters adorn the windows. A small seating arrangement is visible to the right, enhancing the outdoor space.

Home in Ossaia

700 year old restored tuscan home

CorinneRating, 5 stars3 weeks ago

liesl’s home was such perfect stay for our time in cortona. it is just a short drive from the city. the home has such a wonderful view and the beds were comfortable. I would definitely come back again to visit!

5 out of 5 average rating, 13 reviews

A rustic stone building is framed by lush greenery and manicured lawns. An outdoor dining area under a trellis offers a shaded space with a table and chairs. Two chimneys rise from the roof, while the bright blue sky enhances the serene atmosphere.

Farm stay in Camucia

The Garden of Olives | Casa Ippocastano

TheresaRating, 5 stars1 month ago

Beautiful Farmhouse. Lovely place even better in person. The grounds are large and lovely. Great pool. You look out to the town of Cortona from the bedroom and kitchen windows. So relaxing super close a 10 min drive to Cortona 30 mins to Montepulciano. A great base to explore. Host super responsive we were late checking in sure to train delays and it wasn’t a problem. Even got to experience some of Federica’s fabulous wine. Would come back for sure it’s a gem.