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Apartment vacation rentals in Cortona

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Top-rated apartment rentals in Cortona

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Top guest favorite
A spacious living area is showcased with large windows offering panoramic views of the surrounding hills. A dining table sits in the center, accompanied by chairs, while a comfortable seating arrangement is positioned nearby. Natural light fills the space, highlighting the earthy tones and wood accents.
Apartment in Montepulciano
4.97 out of 5 average rating, 443 reviews

A view from the top, Montepulciano

A View From the Top is an apartment in the most peaceful part of Montepulciano(castoldi apartments site) The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills Our wine tasting is sometimes available in season, the new garden for all the guests of our 4 apartments and from 2026 grilled meat( 7pm) Guests will park close the apt ,in the street 50 mt away.

Top guest favorite
A spacious bedroom features a king size bed adorned with light bedding, complemented by decorative pillows. A chair is positioned near the window, which opens to a small private terrace with greenery visible. Iroko wooden parquet flooring adds a warm touch.
Apartment in Cortona
4.99 out of 5 average rating, 184 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.

Top guest favorite
A panoramic view of the Valdichiana landscape, showcasing rolling hills and the town below. The warm colors of a sunset create a tranquil atmosphere, while rooftops of historic buildings in the foreground are visible, adding depth to the scenic backdrop.
Apartment in Cortona
4.93 out of 5 average rating, 165 reviews

"La finestra sulla Toscana", vista incantevole

Appartamento ristrutturato di recente in stile toscano situato nel centro storico di Cortona, a pochi passi dai luoghi di interesse, gode di una vista incantevole sulla Valdichiana. All’interno di un palazzo storico, con ingresso comodissimo, composto da soggiorno con divano letto matrimoniale e angolo cottura,una camera matrimoniale, una cameretta convertibile in un'ulteriore camera matrimoniale e bagno spazioso con doccia. Tutte le stanze hanno finestre sull’esterno verso la Valdichiana.

Top guest favorite
A spacious piazza is surrounded by elegant medieval architecture, featuring a central hexagonal area with open-air seating. Stone pathways lead to various shaded spots, while umbrellas provide shelter for patrons. Beautiful clouds drift overhead, enhancing the vibrant scene of daily life in the historical center.
Apartment in Arezzo
5 out of 5 average rating, 153 reviews

Piazza Grande Boutique Apartment

Affacciato sulla più bella piazza del centro storico di Arezzo, dove si svolge la rievocazione della Giostra del Saracino, il Piazza Grande Boutique Apartment è situato al secondo piano di un palazzo medievale, con vista sui bellissimi palazzi e le Logge Vasariane ed è una location unica nel suo genere. L'arredamento, opera della contessa Cesaroni Venanzi è stato realizzato con bellissimi mobili antichi reinterpretrati in chiave moderna ed arricchiti da contaminazioni contemporanee.

Top guest favorite
A spacious living area is presented with a patterned sofa and a glass coffee table. Warm wood beams accent the ceiling, and a soft rug covers the floor. Light flows through the room, creating a comfortable and inviting space with access to other areas of the apartment.
Apartment in Cortona
4.96 out of 5 average rating, 134 reviews

LA PICCOLA TERRAZZA

La piccola terrazza si trova nel centro storico di Cortona. Cortona è un piccolissimo paese della toscana vicinissimo alla splendida Firenze alla suggestiva Siena; alle bellezze del lago trasimeno . La piccola terrazza vi offre un appartamento all'interno di un palazzo storico composto da ingresso camera matrimoniale; camera con 2 lettini singoli cucina attrezzata e sala pranzo; bagno con doccia; e la splendida terrazza vista lago per poter sorseggiare un buonissimo vino a fine serata

Top guest favorite
A spacious living area features a comfortable purple sofa and striped poufs, complemented by a classic wooden sideboard and elegant lamps. Warm colors adorn the walls, and a large artwork adds character. Natural light enters through multiple windows, enhancing the inviting ambiance.
Apartment in Cortona
4.97 out of 5 average rating, 186 reviews

CasaNella: centrale, luminosa, e panoramica

Accogliente, elegante e delizioso appartamento nel centro di Cortona, con un panorama incantevole che spazia dal Lago Trasimeno alla Valdichiana. Accuratamente arredato, è il luogo ideale per trascorrere qualche giorno in questa meravigliosa cittadina. A due passi dalla strada principale, ma in una posizione silenziosa e panoramica. Parcheggio gratuito a breve distanza. Dotato di riscaldamento ed aria condizionata. Disponibile WiFi ad alta velocità. Ottimo per smartworking.

Top guest favorite
The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.
Apartment in Cortona
4.96 out of 5 average rating, 416 reviews

Cortona Shabby Chic House - independent & balcony-

Questo è un appartamento curato da una Superhost che vive Cortona ogni giorno. 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, con balcone. Arredato con cura, dotato di tutti i comfort per un totale relax

Top guest favorite
A cozy room features a spacious bed against a white wall, complemented by rustic wooden beams and an inviting reading chair. A dining table is set with floral arrangements and tableware. Natural light is seen streaming through the open door leading to the garden.
Apartment in Monticchiello
5 out of 5 average rating, 102 reviews

Casa Tòrta - comfort room

Casa Tòrta consists of a bedroom, reading room and bathroom, perfect for a short stay or for long periods, having reception services available. In the historic center of Monticchiello, there is this building that dates back to 1200. The large double bed is located in the main room with a fireplace stove with ancient charm. In the brightest room a reading lounge, then the green bathroom with shower.

Top guest favorite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Apartment in Montalcino
4.99 out of 5 average rating, 117 reviews

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

Top guest favorite
A small round table is set on a balcony, accompanied by two white chairs. A bottle of wine and two glasses are positioned on the table. The railing features decorative ironwork, framing a panoramic view over the terracotta rooftops and the valley below.
Apartment in Cortona
4.97 out of 5 average rating, 179 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"

Top guest favorite
A serene outdoor space is framed by tall, leafy trees, creating a natural canopy. Within the gravel area, terracotta pots with greenery are visible, offering a sense of tranquility. The expansive view stretches across the hills and valleys of the surrounding landscape.
Apartment in Cortona
4.96 out of 5 average rating, 191 reviews

Casa Le Contesse

È un piccolo appartamento, porzione della casa colonica dove vivo. È situato a piano terra, con accesso indipendente, in collina, in mezzo agli olivi, ad un km da Cortona. C'è possibilità di parcheggio, accesso privato, usufruire del giardino "superpanoramico''

Top guest favorite
The image captures a charming stone exterior framed by blooming flowers and greenery. A doorway with a blue grille leads into a historic building, while the gravel pathway invites exploration. Soft evening light enhances the warm tones of the stone walls.
Apartment in Castiglioncello del Trinoro
5 out of 5 average rating, 363 reviews

Stunning Tuscan apartment in 14 Century Palazzo

L'appartamento si trova al terzo piano di un edificio risalente al 1400,il borgo di Castiglioncello del Trinoro risale al1100,si affaccia sulla val d'orcia con vista a 360 gradi.

Popular amenities for Cortona apartment rentals