Holiday rentals in Penna San Giovanni

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.

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

Casa Janna Cottage | Pool + 2 En-Suites

A two-storey countryside house in the Marche hills, hosted by locals and shaped by food, nature, and a slow rhythm. A boutique stay with seasonal organic breakfast included. The house sleeps up to 4 guests and is fully independent, with living area, kitchen and 2 bedrooms. Private garden with dining and a premium two-person hammock. Shared pool for a small number of guests only (max 8 in tot) surrounded by rolling hills. Ideal for couples, friends or families seeking calm and a refined stay.

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.

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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Guest favourite

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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Guest favourite

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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Guest favourite

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 by adapting the old farmhouse to the latest anti-seismic regulations. The decor is a right mix of modern and ancient, elegant but functional. Outside there is a large private area available for guests, with shaded dining area and private barbecue. Complete the property with a 12x4.5 pool with shaded porch available for guests to enjoy.

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Guest favourite

Frescoes and Centuries-Old Park– Villa Mastrangelo

Well-known residence in our area You can easily find us online as a local tourist landmark. 1️⃣ Self check-in available at any time 2️⃣ Discounts for longer stays (contact me for details) 🏰 Entire villa of over 600 m² 🌿 Centuries-old park of 2000 m² – pet friendly 🚗 Private parking, both open and covered – free of charge 📶 Air conditioning, fast Wi-Fi and Smart TV ☕ In the kitchen: coffee, tea, oil, vinegar, sugar, salt, etc. 🧺 Bed linen, towels and soap included

The house in the old granary

The country farm, surrounded by olive trees and centuries-old oaks, will be all for you just 25 minutes from the sea and an hour from the Sassotetto ski slopes. Ideal for couples or families looking for relaxation, our house is immersed in a silence of yesteryear. You are a 10-minute drive from Macerata and half an hour from the beaches. The space will be at your exclusive disposal. We have a Home Theater with HiFi system. A wood-burning oven is available upon request.

VILLA SERRA - Sibillini Retreat

COMPLETELY RENOVATED - NEW OPENING 2026 Villa Serra Sibillini Retreat is a detached property with a large garden overlooking the Sibilla and Vettore mountains. The property has three double bedrooms with high-quality king-size Reactive mattresses, one of which has twin beds that can be separated upon request. It now offers spa services, a Finnish sauna overlooking the Sibilla, and a heated whirlpool tub, included with your reservation year-round.

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Guest favourite

L'Attico Sul Fiume center home

Elegant and cozy penthouse in a strategic position a few meters from the central Piazza del Popolo and the city's main points of interest within walking distance. The apartment consists of a bright entrance hall, a living room with an island kitchen, two bedrooms both with TV and bathroom, 2 large panoramic terraces and private parking. The hot tub has an additional cost. In the event that two guests wish to use both rooms, there is a surcharge.