Holiday houses in Penna San Giovanni

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Top-rated holiday rentals in Penna San Giovanni

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Guest favourite

A tranquil salt-water pool is surrounded by lush gardens filled with blooming flowers. Lounge chairs are positioned along the poolside, offering views of rolling hills under a clear blue sky, enhancing the serene atmosphere of the outdoor space.

Home in Falerone

4.89 out of 5 average rating, 18 reviews

Farm house with exclusive access to the pool

Immersed in the quiet countryside with a 360 view on the surrounding hills, the farm house has typical rustic Marchigiano style with original beams and floors and it is surrounded by a big garden rich in flowers. The pool has a very panoramic and relaxing area. It is the ideal place for people who love silence, nature and enjoy to admire the beautiful landscape and the stars lit sky. The Sibillini Mountains National park and the beaches are just 40 min drive away Right place for cycling lovers.

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Villa in Gualdo

5.0 out of 5 average rating, 3 reviews

Luxury Villa 8p | Scenic views | Heated Pool | A/C

An exclusive private villa in Le Marche near Gualdo, designed for refined living and total privacy. Accommodating up to 8 guests. It offers 4 elegant bedrooms with airco, 180×200 cm double bed and 4 bathrooms. The interior is a seamless blend of timeless Italian character and contemporary comfort. Unwind by the heated pool with sweeping views of the Monti Sibillini or enjoy long, relaxed dinners in the outdoor kitchen. A serene retreat for those seeking beauty, tranquility and understated luxury

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Guest favourite

An inviting dining setting is showcased on a loggia, featuring a table set with plates and glasses. Two reclining chairs are positioned nearby, framed by an archway that reveals a stunning view of rolling hills and mountains in the background.

Home in San Vittoria in Matenano

4.84 out of 5 average rating, 43 reviews

Views from the roof of Le Marche

Welcome to real Italy. This is a unique home, named locally as Casa Matita (The Pencil House). It has an awesome view awaiting you from the loggia (roofed terrace). Relax, read, drink prosecco or dine while watching amazing sunsets in the peaceful medieval village of Santa Vittoria. At the top of the hill-top village, the house enjoys a 180-degree panorama of the sea and the mountains (both 45 mins). Recently restored, with three double bedrooms, parking 50m and shops/bakery/taverna 200m.

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Guest favourite

A serene garden area is surrounded by lush greenery and colorful flowers. A stone pathway leads through the garden, with a cozy outdoor seating area partially shaded by a pergola. The hillside in the background is adorned with trees displaying autumn colors.

Home in Saletta

4.91 out of 5 average rating, 11 reviews

Casa Eola Semi detached two bedroom rural cottage.

Forget your worries in this spacious and serene space. This semidetached haven is off the beaten track in a quiet valley with stunning views of hip top villages. The gardens, with plunge pool, are the perfect place to relax. The Marchigiano countryside is waiting to be explored for those who love walking, painting, or discovering vineyards, markets, restaurants and bars. All within easy reach. Both the coast and the spectacular Sibillini mountains are approximately a 35 minutes drive away.

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Guest favourite

A serene swimming pool is situated on a deck, featuring clear turquoise water under a bright sky. An umbrella provides shade beside chaise lounges. Scenic hills and mountains stretch into the distance, creating a picturesque backdrop of nature.

Home in Penna San Giovanni

5.0 out of 5 average rating, 8 reviews

GrazieSole Agriturismo exclusive whole house

The GrazieSole farmhouse is a newly renovated 1900s farmhouse, in a characteristic style with original stone walls, exposed bricks and ceilings with wooden beams, it has a 12-metre swimming pool with breathtaking views and a wide panorama that extends from the Sibillini Mountains to the adjacent hillside villages. It is located in open countryside one kilometer from the center of the village of Penna S. Giovanni, in a sunny and quiet position, surrounded by a garden and large green spaces.

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Top Guest favourite

The image captures a serene sunset over a private pool, with lush green grass surrounding the area. Sunlight casts a warm glow on the villa's exterior, highlighting large windows that reflect the fading daylight. Trees and hills are visible in the background, enhancing the peaceful setting.

Villa in Servigliano

4.97 out of 5 average rating, 34 reviews

Villa with exclusive private, heated pool

Villa del Sole is a beautiful retreat nestled amidst the typical verdant hills of the Marche region. It's located just 35 minutes away from the stunning beaches of Porto San Giorgio. This newly built accommodation offers all the comforts that you could ask for. The villa is fully enclosed with wired fencing and surrounded by a gorgeous garden, making it pet-friendly. Guests can enjoy the heated pool, which is exclusively for them and enhanced with a winter cover from October through March.

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Top Guest favourite

Vibrant sunflowers bloom in the foreground, creating a lively scene against the rolling hills of Le Marche. A rustic stone building is positioned amidst lush greenery, while the expansive landscape showcases fields and distant towns under a clear blue sky.

Apartment in Mogliano

4.98 out of 5 average rating, 46 reviews

Experience Authentic Italian Village Life

Located in the heart of Le Marche, ranked 2nd in Lonely Planet’s 2020 list of “Top 20 Regions in the World to Visit.” This spacious apartment and garden offer the perfect base to relax or explore. Within 40 mins’ drive of mountains, lakes, and the sea, with many ancient hilltop towns nearby. Just 5 mins from Mogliano, where you’ll find everything you need for your stay. Nature reserves, outdoor markets, health spas, hiking, biking, and riding trails are all within easy reach.

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Top Guest favourite

A bright kitchen area features modern appliances, including a retro-style refrigerator. A wooden dining table is set for a meal, surrounded by white chairs. Natural light enters through multiple windows, complementing the warm, rustic tones of the stone flooring and beams.

Apartment in Monsampietro Morico

5.0 out of 5 average rating, 45 reviews

Casale Biancopecora, Casa Cerqua

Apartment Casa Cerqua of 100 square meters finely furnished, we have recovered all the old materials of the house in the recent renovation adapting the old house to the latest seismic regulations. The furniture is a right mix of modern and antique, elegant but functional. Outside there is a large private area at guests' disposal, with a shaded dining area and a private barbecue. Complete the property with a 12x4.5 swimming pool with shaded porch available to guests.

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Top Guest favourite

A charming, two-story farmhouse features terracotta walls and a sloped roof, surrounded by lush greenery. Potted plants frame the entrance, with a wooden table and chairs positioned outside under a shaded umbrella, offering inviting outdoor seating and scenic countryside views.

Villa in Sant'Angelo in Pontano

4.98 out of 5 average rating, 43 reviews

Traditional 3-bedroom cottage with large garden

Forget your worries in this spacious and serene space. Absolutely tranquil, but less than a five minute drive from the bustling village of Sant’Angelo, which has three restaurants, three bars, and a theatre, as well as all local services. Relax and enjoy the views in the garden, or drive half an hour to the beach or a lake in the mountains, or explore the many beautiful hilltop towns in the area. Something for all tastes!

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Guest favourite

A gravel driveway leads to a charming two-story villa surrounded by lush greenery. The building features a mixture of stone and brick walls, framed by large windows with red shutters. Sunlight filters through the trees, creating a serene atmosphere.

Home in Serra

4.94 out of 5 average rating, 35 reviews

villa Strada

NEW FOR '26: Private rooftop Jacuzzi for up to 4 people. Opportunity to enjoy horse-drawn carriage rides along the scenic white roads of Montefortino. Nestled in the heart of the Sibillini Mountains, Villa Strada boasts breathtaking views of Mount Vettore and Mount Sibilla. This elegant 1990s villa combines timeless charm with modern comfort, featuring welcoming and harmonious spaces immersed in nature.

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Top Guest favourite

Villa in Sant'Angelo in Pontano

5.0 out of 5 average rating, 5 reviews

Villa in the Sibillini Mountains, Pool & Privacy

Private pool villa in Sant’Angelo in Pontano, among the rolling hills of Marche at the foot of the Sibillini Mountains. Sleeps up to 8 with 4 double bedrooms, all with en-suite bathrooms (3 upstairs + 1 in a separate annex), Wi-Fi and air conditioning. Large shaded porch for outdoor dining, lounge corners, and an outdoor BBQ/oven area. Great base for the Sibillini Park and Lake Fiastra.

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Guest favourite

A refreshing salt-water pool is surrounded by lush greenery and neatly trimmed shrubs. Poolside, comfortable lounge chairs are arranged for relaxation. In the backdrop, a rustic building blends harmoniously with the rolling hills under a dramatic sky.

Home in Loro Piceno

4.91 out of 5 average rating, 81 reviews

Country House with Pool and Garden

Country house with swimming pool and garden - The farmhouse with swimming pool is located in the countryside with well-kept and completely renovated furnishings, for a relaxing vacation 5 km from the Fiastra Abbey Nature Reserve, 30 km from the entrance to the Monti Sibillini Park, 30 km from the Adriatic Sea and 60 km from the Conero Riviera.

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