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Apartment holiday rentals in Cortona

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Top-rated apartment rentals in Cortona

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Top guest favourite
A small balcony is featured with two black woven chairs flanking a round table. On the table, a bottle and two glasses are set against a backdrop of panoramic views of rolling hills and terracotta rooftops under a partly cloudy sky.
Flat in Cortona
4.99 out of 5 average rating, 175 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 favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Flat in Montepulciano
4.97 out of 5 average rating, 150 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Top guest favourite
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.
Flat in Cortona
4.93 out of 5 average rating, 163 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 favourite
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.
Flat in Cortona
4.96 out of 5 average rating, 126 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 favourite
The studio features a well-lit open space with two large windows bringing in natural light. A cozy double bed is placed alongside a bright orange sofa. A dining table for four is set near the kitchenette, which includes wooden cabinetry and essential appliances.
Flat in Cortona
4.87 out of 5 average rating, 102 reviews

Monolocale Cortona per vacanze

Vacanze a Cortona in una splendida città storica in provincia di Arezzo. Monolocale in centro storico, al primo piano di un antico palazzo, a 50 metri dalla piazza principale, recentemente ristrutturato, angolo cottura, riscaldamento autonomo, Wi-Fi gratuita, ideale per singolo o coppia anche per brevi periodi e week-end. Sono presenti alcuni parcheggi "free", per auto e moto, a breve distanza dall'appartamento, lungo le mura storiche della città. CIN IT051017C2VLROXHO6

Top guest favourite
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.
Flat in Cortona
4.97 out of 5 average rating, 182 reviews

CasaNella: luminosa, centrale 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.

Superhost
A round dining table is set on a terrace, surrounded by woven chairs. A colorful yellow vase filled with pink flowers is at the center. The view reveals rolling hills and a clear sky, providing a serene backdrop to outdoor dining.
Flat in Montepulciano
4.82 out of 5 average rating, 115 reviews

Casa Evelina - Incredible View, Central Location

Benvenuti nel cuore del centro storico di Montepulciano. Questa casa esclusiva unisce spazio, comfort e un’autenticità rara: un luogo ideale per famiglie, gruppi di amici o ospiti in cerca di un soggiorno memorabile in una delle città più affascinanti della Toscana. Qui potrete vivere Montepulciano da una prospettiva privilegiata: uscire di casa e trovarvi immediatamente immersi tra palazzi rinascimentali, botteghe artigiane, cantine storiche e ristoranti tipici.

Guest favourite
A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.
Flat in Montepulciano
4.91 out of 5 average rating, 278 reviews

I Tramonti di Eramo, Montepulciano centro.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

Top guest favourite
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.
Flat in Cortona
4.97 out of 5 average rating, 412 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

Guest favourite
A light-filled kitchen area features a wooden table set with breakfast items, including pastries and drinks. An elegant wooden cabinet showcases decorative items. Large windows provide views of the historic buildings outside, including clock tower details, while exposed wooden beams add character to the ceiling.
Flat in Cortona
4.89 out of 5 average rating, 158 reviews

Baldelli | Apartment in the city's main square

This apartment, named Baldelli, is located in Piazza della Repubblica and it’s a the third floor of an historic building without elevator. The apartment has a double bedroom, a living room with desk and a sofa, a bathroom with shower, a kitchen full equipped. From one side of the house you can see the city hall building and from the other one there is a great Val di Chiana view.

Top guest favourite
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.
Flat in Cortona
4.97 out of 5 average rating, 175 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 favourite
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.
Flat in Cortona
4.96 out of 5 average rating, 186 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''

Popular amenities for Cortona apartment rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Arezzo
  5. Cortona
  6. Flat rentals