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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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Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino
4.9 out of 5 average rating, 240 reviews

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

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
4.96 out of 5 average rating, 78 reviews

The Balsaccia

Surrounded by the greenery of the Tuscan countryside, between the hermitage of Cerbaiolo and the Little Diary Museum, and just a few minutes from the sites of Piero Della Francesca, a brand-new, modern, and cozy cottage with ample indoor and outdoor spaces to enjoy the greenery and tranquility. The apartment has an open 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 wardrobe, bunk bed and bathroom.

Top Guest favourite
An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.
Villa in Cortona
5.0 out of 5 average rating, 96 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

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
4.99 out of 5 average rating, 83 reviews

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.

Top Guest favourite
An aerial view of a rustic villa is framed by lush greenery, showcasing a stone exterior and terracotta roof tiles. A salt-water pool is situated nearby, surrounded by outdoor seating. The tranquil landscape of hills is visible in the background under warm evening light.
Home in Poppi
5.0 out of 5 average rating, 66 reviews

Villa Podere Cerretino

Podere Cerretino is the perfect place to find and discover your own tranquility and relaxation. A corner of paradise surrounded by the picturesque hills of Tuscany in an enchanting landscape, located in a central and strategic position to visit the most interesting places in Tuscany, such as Florence, Siena, Arezzo. The Villa consists of 4 completely independent apartments and an elegant panoramic veranda where you can gather and enjoy a unique vacation.

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
4.97 out of 5 average rating, 156 reviews

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.

Guest favourite
Apartment in Sansepolcro
5.0 out of 5 average rating, 8 reviews

[Bridgerton Atmosphere] Historic residence in the village

Welcome to my beautiful new home in Sansepolcro! Just completely renovated, it's as fresh as a daisy, but with a bit of a Bridgerton style, so it's historical, themed, and classic 😃 ​🌿 An oasis of natural freshness: Located in a historic building in the center 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.

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
4.87 out of 5 average rating, 164 reviews

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.

Top Guest favourite
The outdoor pool area is surrounded by neatly trimmed cypress trees and colorful gardens. A gentle slope leads to the pool, with views of the rolling green hills in the background. Sun loungers and umbrellas are placed around the pool, creating a serene atmosphere.
Farm stay in Anghiari
5.0 out of 5 average rating, 56 reviews

Tuscan dream lux 2-bed, pool, private balcony

Explore Tuscany in a beautifully decorated 2-bedroom, 2 bathroom apartment with all amenities & a log fire. Welcome to your luxurious home in the heart of Tuscany, Italy, where every moment will be a new adventure. This beautifully designed and well-furnished apartment is located in a restored farmhouse, surrounded by olive groves, vineyards, and rolling hills, offering you the best of Italian living.

Guest favourite
A charming rural building is set against a backdrop of lush greenery at dusk. Soft lighting highlights the stone exterior and terracotta roof, while the surrounding trees and landscaped grounds enhance the tranquil environment.
Farm stay in Anghiari
4.95 out of 5 average rating, 124 reviews

Mafuccio Farmhouse - "Casa di Rigo"

Casa di Rigo is the smallest apartment of Agriturismo Mafuccio, a farmhouse immersed in unspoiled nature in the Sovara Valley, a stone's throw from the Rognosi Mountains nature reserve and nestled at the foot of Monte Castello. A quiet and peaceful place like the streams that cross the valley, where you can find peace, and fully experience nature... in the company of the Valley Kids!

Guest favourite
A spacious room features two large windows adorned with light curtains, allowing natural light to fill the space. A double bed is dressed in a patterned quilt, accompanied by a wooden chair and a simple desk. A shelf holds books and decor items, enhancing the cozy environment.
Apartment in Pieve Santo Stefano
4.95 out of 5 average rating, 167 reviews

Studio apartment "Elsa" on the path of St. Francis

The “Angolo di Elsa” studio apartment is located on the path of the Cammino di S. Francesco, a 2-minute walk from the Museum and Archives of the Diary of Pieve Santo Stefano. Easily reachable by car or bus, it is located on the ground floor. You can spend relaxing days and enjoy wonderful day trips to learn about the nature, history and art of the Upper Tiber Valley.

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
4.99 out of 5 average rating, 271 reviews

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 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.

Popular amenities for Pieve Santo Stefano holiday rentals