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Holiday houses in Pennabilli

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Top-rated holiday rentals in Pennabilli

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

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Top Guest favourite
An outdoor terrace features a stone wall on one side and metal railing that opens to scenic valley views. A table is surrounded by several wrought-iron chairs, all shaded by a retractable canopy. Light flows through white curtains, creating a serene atmosphere.
Earthen home in Pennabilli
4.96 out of 5 average rating, 26 reviews

Villa Elisa with a view

The house, of ancient origins and one of a kind, has a structure divided into several levels of modest size with original and suggestive environments. At street level, there is the entrance to the sitting area and a bathroom with terrace. Going up the stairs, you access the sleeping area with 1 double bedroom overlooking the valley and 1 single open space with bunk bed and window overlooking the village. On the lower floor, the kitchen complete with appliances gives access to the exclusive and private garden.

Guest favourite
A serene sleeping area features a spacious bed with neutral bedding, complemented by a rustic stone wall. A small bedside table with a lamp is positioned next to the bed, while soft natural light fills the room from a window adorned with light curtains.
Home in Mercato Saraceno
4.96 out of 5 average rating, 24 reviews

Casa del Moro

Our house, Casa del Moro, is located in the ancient historic centre of a century-old village in the Savio valley. The ancient village in which it is located, Mercato Saraceno, already existed in 1153 when Saraceno degli Onesti wanted to create a market near the water mill, on the open space near the river with the only bridge over the Savio between Cesena and Bagno di Romagna. Casa del Moro has maintained the style of the medieval village, adding elements of recovery to support its centuries-old identity.

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
4.99 out of 5 average rating, 497 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 favourite
A spacious bedroom is presented featuring two beds, one being convertible, and artwork depicting a mountain landscape. Natural light enters through a nearby window, enhancing the modern decor. A small bedside table and decorative elements, including a plant, add warmth to the space.
Home in San Marino
4.99 out of 5 average rating, 167 reviews

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

Top Guest favourite
An outdoor dining area features a large table set for four under a spacious umbrella. Two lounge chairs are positioned nearby, surrounded by stone pavers and potted plants. The charming facade of the villa can be seen in the background, enhancing the peaceful ambiance.
Apartment in Arezzo
4.97 out of 5 average rating, 91 reviews

Villa Medici Donnini Deluxe Apartment

The apartment consists of the ground floor of Villa Medici Donnini. The property dates back to the 18th century and is located on top of the prestigious hill of San Cornelio, whose archaeological area is one of the 28 Symbolic Places of Peace in the World according to Unesco. The apartment features fine furniture, paintings and drawings dating back to the 18th century, crystal chandeliers, Murano glass lamps and various curious objects. The property is only a 5 minute drive from the city center.

Top Guest favourite
Home in San Leo
4.97 out of 5 average rating, 32 reviews

San Leo Historic Center A/C Relax

Small house, quiet and romantic, renovated, with air conditioning, in the historic center of San Leo. The house can be reach by walk via a comfortable staircase from Piazza Dante and overlooks a small garden. All tourist attractions are within walking distance, as well as car parks, minimarket, bars, restaurants, artisan shops,farmacy and the famous Cagliostro Fortress. Ideal location to discover the historical and naturalistic beauties of Montefeltro region, riviera Romagnola and San Marino.

Top Guest favourite
Villa in Bertinoro
4.97 out of 5 average rating, 75 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.

Guest favourite
Place to stay in Arezzo
4.94 out of 5 average rating, 49 reviews

Glamping boutique, quiet luxury and privacy

Architectural Safari Lodge Solid Wood Decking Private Estate Forget everything you know about camping. Step into a 50sqm suite where fine wood meets oriental fabrics and modern comfort. Wake up in a four-poster bed as the lake view pours through large floor-to-ceiling windows, explore the night sky with your private telescope, or relax among hand-picked rugs. Outside, your private pool and professional outdoor kitchen await for an experience of total privacy and pure luxury."

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, 203 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.

Guest favourite
A quaint stone building is visible across a rustic bridge surrounded by lush greenery. Colorful flower pots line the railing, enhancing the natural scenery. The bridge leads to a serene setting with trees providing shade, creating a peaceful atmosphere for leisurely walks.
Home in Bibbiena
4.92 out of 5 average rating, 66 reviews

Charming house of the past next to the stream.

CASA LISA is part of a small 19th-century village with an old mill where time seems to have stopped. Immersed in lush nature, it invites you to take beautiful walks and hikes. In the stream that flows nearby, you can bathe in the large pools of the waterfalls or relax on its rocks. Children love to play in the small pools. We have lovingly renovated Casa Lisa while preserving its authenticity and personality. Here it is not just a place to stay but an experience

Guest favourite
An entrance to a stone and wood cottage is visible, showcasing a wooden door flanked by a vintage-style light fixture. The surrounding area features a gravel path, with stone walls creating a rustic aesthetic. A vehicle is parked nearby, hinting at accessibility.
Tiny home in Pennabilli
4.89 out of 5 average rating, 18 reviews

Villetta Vittoria -Country House-the barn

The beautiful setting of this romantic place a stone's throw from Pennabilli will leave you speechless. A small stone and wood house with a courtyard of about 300 meters with pergola, table and barbecue. The annex of Villetta Vittoria was built after renovating a small barn. The bed is housed in the loft, which is accessed by a typical ladder. The furniture features a 1900s desk, a 1800s bookcase and a sofa bed. Refrigerator, kettle and coffee maker.

Top Guest favourite
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.

Popular amenities for Pennabilli holiday rentals

  1. Airbnb
  2. Italy
  3. Emilia-Romagna
  4. Rimini
  5. Pennabilli