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Holiday rentals in Sestino

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Top-rated holiday rentals in Sestino

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

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

4.9 out of 5 average rating, 240 reviews
Top guest favourite
Home in San Marino

House "Independent" close to the Historic Center

This independent house, located a few steps from the walls surrounding the historic center of the Republic of San Marino, is the top place for those seeking relax, privacy and a breathtaking view of the surrounding mountains. The house, modern and with attention to detail, is perfect for families, couples or small groups who want to live an unforgettable experience. Large and well-organized spaces are designed for your every comfort. Free parking a few steps from the front door. Pets are welcome

4.98 out of 5 average rating, 196 reviews
Top guest favourite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

4.99 out of 5 average rating, 113 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, 83 reviews
Guest favourite
Two cocktails with fresh fruit adorn a table. A straw hat rests nearby, while a serene view of a pool and rolling hills unfolds in the background, under a clear blue sky.
Villa in Urbania

Villa del Duca - Private villa with pool

Surrounded by the harmonious landscape of Le Marche region, Villa del Duca is a private villa with a swimming pool, located just a few kilometers from Urbania, a peaceful and welcoming town offering all the services needed for a comfortable stay. Set in the countryside, the villa features an infinity pool with panoramic views, accessible via a scenic path lined with aromatic herbs, plants, and flowers, making the walk a true delight for all the senses.

4.94 out of 5 average rating, 17 reviews
Guest favourite
A stone terrace is framed by arched supports, illuminated by gentle lighting. Wooden furniture is arranged for relaxation, with potted plants adding natural elements. The backdrop showcases the medieval bridge, seamlessly integrating the outdoor space with the historic architecture.
Home in Mercatello sul Metauro

The house on the bridge

You will live in a house hundreds of years ago, built on the Romanesque bridge of the village. Large walls, oak beams, terraces under the arches of the bridge and bowls on the road in the warm embrace of a medieval village. Madies, pastry chefs, chests wisely renovated to leave all the flavor of the crafts that still belong to us. Breakfast with the best traditional desserts and pleasant breaks by the lit fireplace. Time will seem to stop with you.

4.95 out of 5 average rating, 59 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, 157 reviews
Guest favourite
Flat in Sansepolcro

[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 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, 8 reviews
Superhost
Villa in Urbania

Villa with Private Pool for 12 guests: Urbania

Surrounded by greenery just 7 minutes from the center of Urbania, our country house offers space, comfort and relaxation. With 6 large bedrooms, 6 bathrooms, 2 equipped kitchens and 12 beds, it is perfect for groups and families. Enjoy the pool, barbecue area and huge private garden. Ideal for those seeking tranquility without sacrificing the proximity of the town and its services. An oasis of peace in the heart of the Marche region!

4.9 out of 5 average rating, 10 reviews
Top guest favourite
The rustic stone farmhouse is illuminated softly against the evening sky, surrounded by lush greenery. An external staircase leads to the entrance, while various trees and plants create a natural boundary around the property, enhancing its tranquil ambiance.
Farm stay in Anghiari

Mafuccio Farmhouse - "Casa di Osvaldo"

Casa di Osvaldo is the largest apartment of Agriturismo Mafuccio, a farmhouse immersed in unspoiled nature in the Sovara Valley, a stone's throw from the Monti Rognosi 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 Boys!

4.99 out of 5 average rating, 84 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 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, 271 reviews
Superhost
The rustic stone building is illuminated softly in the evening, revealing warm lights from the windows. A spacious courtyard is visible, featuring a planted area and paths leading to the entrance. Nearby trees and greenery frame the serene outdoor space.
Holiday home in Sestino

The Three Sources

This enchanting vacation home is housed inside a stone farmhouse with a rustic profile cared for in every detail nestled in the Tuscan countryside in an unspoiled environment overlooking the rows of vines placed at the foot of the Sasso Simone massif. A haven of peace and tranquility for those who wish to get away from the hustle and bustle of daily life.

4.75 out of 5 average rating, 20 reviews

Popular amenities for Sestino holiday rentals