Holiday houses in Pieve Santo Stefano

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Top-rated holiday rentals in Pieve Santo Stefano

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

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Top Guest favourite

A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.

Farm stay in Ruscello

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

4.99 out of 5 average rating, 535 reviews

Top Guest favourite

An open living space features high wooden beams above a polished floor. A cozy seating area includes an armchair and a small dining table with colorful chairs. A kitchen area is highlighted by a low countertop, with cheerful decor adding warmth to the atmosphere.

Tiny home in Pieve Santo Stefano

The Balsaccia

Nestled in the green Tuscan countryside, between the hermitage of Cerbaiolo and the Piccolo Museo del Diario, and just a few minutes from the sites of Piero Della Francesca, a brand-new, modern and cosy cottage with spacious indoor and outdoor areas to enjoy the greenery and tranquillity. The apartment features an open plan space with a double bed, an armchair, a dining table and a kitchen with an induction hob, an electric kettle and a refrigerator. Room with a wardrobe, bunk bed and bathroom.

4.96 out of 5 average rating, 79 reviews

Top Guest favourite

Apartment in Arezzo

Piazza Grande Boutique Apartment

Overlooking the most beautiful square in the historic center of Arezzo, where the re-enactment of the Giostra del Saracino takes place, the Piazza Grande Boutique Apartment is located on the second floor of a medieval building, overlooking the beautiful palaces and the Vasari Loggias and is a unique location of its kind. The decor, the work of Countess Cesaroni Venanzi, was created with beautiful antique furniture reinterpreted in a modern way and enriched with contemporary influences.

5.0 out of 5 average rating, 155 reviews

Superhost

Villa in Bibbiena

Tuscan Villa 300m² · 6 Bed 5 Bath · Cool Summers

Managed by Evora Homes — Superhost, 4.96★ across all our homes. A 300 m² villa in the heart of the Casentino, the green Tuscany almost nobody knows. 6 bedrooms and 5 bathrooms: ten people sleep comfortably and nobody queues in the morning. Fenced garden with fruit trees, two balconies over the valley, private parking for 3 cars. Cool air even in August — you sleep with the windows open. Bibbiena 5 min · Casentinesi Forests, La Verna and Camaldoli a few km · Arezzo 40 min.

5.0 out of 5 average rating, 3 reviews

Top Guest favourite

The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.

Castle in Ferrano

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

4.99 out of 5 average rating, 227 reviews

Top Guest favourite

The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.

Home in Prato

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 shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

4.98 out of 5 average rating, 145 reviews

Top Guest favourite

The image features a serene outdoor area with a spacious swimming pool surrounded by lounge chairs. Lush greenery and flowering plants line the poolside, while a stone wall and distant hills provide a peaceful backdrop under a clear sky.

Villa in Pieve a Socana

Villa Montanina - exclusive relaxation in Tuscany

A typical Tuscan villa exclusively immersed in the views, greenery and peace of the Casentino Valley where you can spend moments of relax, fun and experiences where nature, culture and taste come together. During your stay you can enjoy cooking classes, yoga classes, wine tastings, massages, personalized experiences and relax in the large swimming pool. The Villa with its many large green spaces is also perfect for celebrating your dream wedding in Tuscany.

4.99 out of 5 average rating, 85 reviews

Guest favourite

Apartment in Sansepolcro

[Bridgerton atmosphere] Historic residence in the village

Welcome to my beautiful new home in Sansepolcro! It has just been completely renovated and is as fresh as a daisy, but with a touch of Bridgerton style, making it historic, themed and classic 😃 🌿 An oasis of natural coolness: Located in a historic building in the centre of Sansepolcro, the apartment boasts thick original stone walls. This traditional insulation keeps the house beautifully cool and pleasant (around 24°C) even on the hottest summer days.

5.0 out of 5 average rating, 10 reviews

Guest favourite

A spacious outdoor area features a clear swimming pool surrounded by lounge chairs. The stone house is positioned on a green hillside, offering views of the surrounding landscape. Shrubs and potted plants enhance the natural setting, contributing to a serene atmosphere.

Apartment in Subbiano

Ginepro apartment, panoramic view with swimming pool

Apartment inside a large house on a hill, with panoramic swimming pool. Nestled in the green hills of Casentino, Il Rifugio del Moro is located on a hill and is the ideal place for those seeking nature without sacrificing comfort. The 'Ginepro' apartment consists of 3 rooms: kitchen/living room with double sofa bed and 2 double bedrooms, as well as a bathroom and a private patio. The apartment is entirely on the ground floor, with independent access.

4.9 out of 5 average rating, 30 reviews

Guest favourite

An ancient stone farmhouse with a rustic red-tiled roof is surrounded by lush greenery. The building sits within a mountainous landscape, framed by trees. The open sky above reveals soft clouds and sunlight, hinting at the serene atmosphere of the rural environment.

Holiday home in Chiusi della Verna

Experience rustic off-grid life in the wilderness

This ancient rustic farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves, the bumpy road and the lack of phone signal offer an authentic off-grid experience. A rare privilege to go into the wild and take a break from urban life and modern conveniences. Hike to the monastery of St.Francis and the sacred forests of La Verna...or simply sit and enjoy the peace of this magical remote place.

4.97 out of 5 average rating, 159 reviews

Guest favourite

A rustic dining area features a long wooden table set for eight, with simple tableware and napkins. A large window allows natural light to fill the space, offering a view of the vibrant garden outside, where a hammock is visible in the background.

Home in Anghiari

PoggiodoroLoft, Tuscan dream e relax

Welcome to Poggiodoro Loft, 16th century stones' villa located in the countryside of Anghiari. Stunning views, charming and furnished interiors providing all type of comforts, the relaxing sauna, the private garden where you can enjoy the open air and lunch under the pergola, BBQ, fantastic in the warm seasons, lounge with brazier a panoramic swimming pool to spend great moments with friends, to be shared with the hamlet guests.

4.87 out of 5 average rating, 167 reviews

Top Guest favourite

A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.

Home in Anghiari

Casa Rosmarino Eco-Wellness Country Home

Price includes: - Infrared Sauna - Wood for Fireplace - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay The house is located inside a Borgo (small group of houses) Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

4.99 out of 5 average rating, 274 reviews