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Apartment holiday rentals in Sestino

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Top-rated apartment rentals in Sestino

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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.
Apartment in Cortona
4.99 out of 5 average rating, 176 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.

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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.
Apartment in Montepulciano
4.97 out of 5 average rating, 153 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

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Top Guest favourite
A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.
Apartment in Montepulciano
4.98 out of 5 average rating, 162 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

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Top Guest favourite
A charming entryway is framed by wooden double doors with decorative handles. A terracotta-tiled step leads to a alcove featuring a colorful artwork, surrounded by white walls and a tall decorative vase with dried branches. Light filters through arched windows above.
Apartment in Monticchiello
5 out of 5 average rating, 104 reviews

“La Vittoria” House

Mine is a beautiful apartment for exclusive use in the center of Monticchiello. Equipped with every comfort, fully equipped kitchen. Linens. Bright living room and two comfortable bedrooms, one of which overlooks one of the main squares of the village and enjoys views of the Val d'Orcia and Mount Amiata. A stone's throw from my Ristorante Daria, one of the best in the area where you can taste good traditional dishes revisited impeccably. I look forward to seeing you! Deborah

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Guest favourite
Apartment in Urbania
4.83 out of 5 average rating, 155 reviews

San Cristoforo - beautiful self-catering apartment

Peaceful apartment with terrace and beautiful mountain views San Cristoforo is a charming cottage in the Marche countryside. Beautiful views and lovely fresh air. Pretty terrace for out of doors dining and relaxing. Well furnished. Charming fireplace. Central heating. Quiet spot. Ideal for visitors to local attractions such as Urbino, Urbania, Gubbio, San Sepolcro, artists, families with children, walkers, lovers of the countryside and local gastronomy. Romantic views.

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Top Guest favourite
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Apartment in Monticchiello
4.97 out of 5 average rating, 181 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a self-contained, non-shared, single-storey apartment located within a villa at the foot of Monticchiello. It features 3 bedrooms, 2 bathrooms, a fully equipped kitchen and a living room. The rooms are furnished in Tuscan style, featuring restored heirloom furniture combined with contemporary elements. The kitchen is fully equipped, and the apartment is surrounded on all sides by a large garden, so that all the rooms offer a beautiful view of the countryside.

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Top Guest favourite
The exterior of a rustic stone building is captured, showcasing a two-story structure with multiple shuttered windows. A small balcony is visible on the upper level. Lush green grass and a few decorative plants frame the entrance, while a vehicle is parked nearby.
Apartment in Urbino
4.96 out of 5 average rating, 204 reviews

Apartment in an old farmhouse 4 km from Urbino

Charming 45 sqm apartment in a finely renovated old farmhouse. On the hills, a 5-minute drive from Urbino, the accommodation is equipped with a kitchen and living room, private bathroom with shower and double bed. Third bed on the mezzanine. Wi-Fi, TV, free on-site parking, mosquito nets, fan, library, informational material for discovering the area. Breakfast is offered for the first 2 days of the stay, after which it will be the customer's responsibility to provide it.

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Guest favourite
The spacious terrace features comfortable seating with green bean bags, a dining table, and lounge chairs. Vibrant pink flowers in the foreground add a pop of color, while the soft tones of the stone building and blue sky create a serene atmosphere for relaxation.
Apartment in Assisi
4.97 out of 5 average rating, 232 reviews

Assisi Al Quattro - Historic Centre of Assisi

Situated on the top floor of an ancient family home in the historic centre of Assisi, a short distance from the magnificent Basilica of San Francesco, “Assisi Al Quattro” is a haven of silence and regeneration, filled with the fragrance of medicinal herbs in summertime: I couldn’t help but falling in love with it. The sweeping views from the large terrace is truly unique, and it is well-worth a visit just to experience it. Everyone is welcome

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Superhost
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.
Apartment in Montepulciano
4.91 out of 5 average rating, 286 reviews

I Tramonti di Eramo, central Montepulciano.

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.

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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.
Apartment in Cortona
4.97 out of 5 average rating, 413 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

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Top Guest favourite
An open living space is characterized by exposed stone walls and wooden ceiling beams. A red sofa is positioned near two windows, providing natural light. A wooden dining table surrounded by chairs invites communal meals, while a wooden cabinet adds practical storage.
Apartment in Gubbio
4.86 out of 5 average rating, 362 reviews

Medieval Suite

An amazing apartment in the historical building of "Bargello" in the heart of Gubbio. Just a few steps away from Piazza Grande. It accommodates up to 5 people in a double bedroom, a double sofa-bed and a single mattress in the living room. Baby crib available upon request. The fireplace unfortunately cannot be used .

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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.
Apartment in Cortona
4.96 out of 5 average rating, 187 reviews

Casa Le Contesse

It's a small apartment, part of the farmhouse where I live. It's located on the ground floor, with independent access, on a hill amidst olive trees, one km from Cortona. Parking, private access, and use of the very scenic garden are available.

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