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Vacation rentals in Montefiorentino

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montefiorentino

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

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Guest favorite
Home in Torriana
4.97 out of 5 average rating, 35 reviews

Villa overlooking Rimini and San Marino

A recently renovated rustic villa overlooking the Romagna coast and San Marino. Three large bedrooms, two bathrooms with two showers, a large living room with a sofa, and a fully equipped kitchen. Immerse yourself in nature and take advantage of the large porch on starry nights. Access the swimming pool just 900 meters away with an adjacent restaurant, at discounted prices. Visit San Marino, Verucchio, Santarcangelo di Romagna, Rimini, Riccione, and much more in just a few minutes. Cin: IT099028C1V8NP8K8F

Top guest favorite
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
4.99 out of 5 average rating, 503 reviews

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.

Top guest favorite
Farm stay in Apecchio
4.97 out of 5 average rating, 34 reviews

Fontesomma Farmhouse - La Cupa - natural relaxation

Beautiful 19th-century farmhouse on the lush and green hills of the Umbrian-Marche Apennines, it will be the ideal place to spend pleasant moments in tranquility in contact with nature. A place to unleash your imagination and lose yourself in the gaze of suggestive sunsets, verdant woods, lush hills and wide valleys, from which it is possible, at times, to see the local fauna roaming free. Equipped with a BBQ, swimming pool with Roman steps and a Jacuzzi, it will be the source of your relaxation!

Top guest favorite
Villa in Bertinoro
4.97 out of 5 average rating, 76 reviews

LUXURY VILLA BELVEDERE - Sea View with Pool & Spa

Providing a truly authentic italian experience, the spacious and gorgeously decorated Villa Belvedere is magnificently set in a unique corner of the ancient village of Bertinoro, with breathtaking views of the peaceful and pictoresque Romagna hills, sea and coastline. Infinity pool heated upon request, hot tub, sauna, steambath, professional gym; cinema room, billiard, bar corner with wine cellar, fully furnished and carefully designed and maintaned garden with barbecue and outdoor games.

Top guest favorite
A spacious bedroom features a four-poster bed framed by a wall adorned with various papers. Nearby, a comfortable seating area includes two chairs and an ottoman. Soft lighting highlights the arching ceilings, contributing to an open and airy feel.
Loft in Arezzo
4.98 out of 5 average rating, 92 reviews

PIETRASERENA Loft in the heart of the historic center

In the heart of medieval Arezzo, PIETRASERENA is a one-of-a-kind vacation home. Located in a prestigious historic building, a stone's throw from Piazza Grande, it was born from the restoration and reuse of what were once artisan and merchant shops since ancient times. A loft characterized by the perspective sequence of vaulted rooms, functionally distinct but left without separations, where pietraserena dominates both in the cladding and in the decorative elements of the cross vaults.

Guest favorite
An aerial view captures the serene property, featuring a lush landscape and a shared swimming pool surrounded by vibrant red umbrellas. The rustic buildings and well-maintained gardens blend harmoniously with the surrounding vineyards, creating a tranquil atmosphere.
Condo in Monte San Savino
4.92 out of 5 average rating, 13 reviews

Casa Tondino | Ground floor 2-bedroom apartment (4

La Foresteria is a historical rural estate located near Arezzo in southeast Tuscany. Surrounded by lush countryside and fruit orchards, it offers guests serenity and peace. The property features ten carefully restored apartments, a private swimming pool, and an on-site restaurant where guests can enjoy breakfast and dinner. Its location is perfect for relaxing or exploring Tuscany’s art, culture, and nearby cities like Cortona, Florence, Siena, and Montepulciano.

Top guest favorite
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
4.96 out of 5 average rating, 54 reviews

The house on the bridge

You will live in a house hundreds of years ago, built on the Romanesque bridge of the country. Large walls, oak beams, terraces under the arches of the bridge, and pebbles on the street in the warm embrace of a medieval village. Madie, pastries, wisely renovated chest of drawers to leave all the flavor of the crafts that still belong to us. Breakfast with the best traditional pastries and pleasant breaks by the fireplace. Time will seem to be stopping with you.

Top guest favorite
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
4.98 out of 5 average rating, 143 reviews

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.

Guest favorite
Farm stay in Cortona
5 out of 5 average rating, 6 reviews

Relaxing-unspoiled country place La Valle...

A panoramic retreat surrounded by greenery, with open views of the valley and the castle. Warm and thoughtfully designed atmosphere, with wooden beams, a fireplace, and modern comforts — ideal for a relaxing stay immersed in the authentic beauty of the Tuscan-Umbrian countryside.The apartment "La Valle" is located on the ground floor of a villa – Rocca di Pierle – nestled in the rolling green hills of the Val di Pierle, just a few kilometers from Cortona.

Top guest favorite
A spacious bedroom features a king-size bed with neutral bedding, complemented by decorative pillows. Soft lighting is provided by wall sconces, while natural stone walls add texture. A small bedside table and an armchair enhance the inviting ambiance.
Home in Sarsina
4.98 out of 5 average rating, 59 reviews

Nature Retreat | Peace & Relax in the Hills

A stone house immersed in nature, in the heart of Romagna, between the Apennines and historic villages. A peaceful and quiet place for those seeking slow living, intimacy and relaxation, with a private hot tub. La Cappelletta holds generations of memories and is now a space to live slowly: sleep, cook, taste, meditate and enjoy the silence. Perfect for romantic stays, escapes from the city, retreats with friends or weekends away from the noise.

Guest favorite
Chalet in San Leo Bastia
4.79 out of 5 average rating, 47 reviews

Casa Isabella - Villa with pool and sauna

Welcome to beautiful Tuscany. The detached Casa Isabella is located on a picturesque hill between Cortona and Città di Castello. Nestled in 20,000 m² of forests and meadows, a stay invites you to long walks, bike rides and saunas. The sunny orientation of the terrace area with a large pool offers plenty of space for sunbathing. Around the Casa there are several cozy seating areas. The wonderful panoramic view is a constant companion.

Guest favorite
Tower in Santarcangelo di Romagna
4.92 out of 5 average rating, 13 reviews

Torre dei Battagli-Dormi in a medieval tower

On the cycle path that leads from Rimini to Valmarecchia stands a medieval tower dating back to the 14th century. Built by a wealthy man from Rimini, Fusso de' Battagli. Once a watchtower of an extensive fortified farm, it guarded wheat and products of the earth. People came here to the ricetto to bake bread. Today this no longer happens, but the tower retains its charm as a fortress in which to relax and feel protected.

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