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Vacation rentals in Penna San Giovanni

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Top-rated vacation rentals in Penna San Giovanni

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

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Guest favorite
Villa in Castelraimondo
5 out of 5 average rating, 9 reviews

Villa Ermelinda · Ville Carborello Weddings

Villa Ermelinda is a private 16th-century villa set among the rolling hills of Le Marche, ideal for intimate weddings, destination weddings and exclusive stays. It offers exclusive use, a panoramic pool, gardens, a big terrace and beautiful spaces for symbolic ceremonies, poolside aperitifs and dinners under the stars. Hosting up to 18 guests, it also works perfectly with nearby Villa Nasca & Villa Adele, just a few minutes away, for larger wedding groups and unforgettable wedding weekends.

Guest favorite
A sleek bathroom is equipped with a glass-enclosed shower featuring ambient lighting and modern fixtures. Adjacent to it, a wooden sauna offers a warm and inviting retreat. The room features wooden flooring, enhancing the overall cozy ambiance.
Vacation home in Amandola
4.95 out of 5 average rating, 43 reviews

House - Il Gioiello - with Jacuzzi and Sauna

The house, immersed in the historic center of the City of Amandola, totally renovated and furnished, has: 2 cozy rooms, a bathroom with sauna and jacuzzi bali Hamman with Turkish bath, a sofa bed in front of the fireplace (not usable), a large living room with kitchen and relaxation area, from which you can enjoy a beautiful view of the Sibillini Mountains. "Il Gioiello" is equipped with a large kitchen furnished and equipped with a ventilated oven, microwave, dishwasher and American fridge.

Superhost
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 Santa Vittoria in Matenano
4.82 out of 5 average rating, 38 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.

Guest favorite
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 out of 5 average rating, 5 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.

Guest favorite
An open living area features a gray sofa adorned with cushions, paired with a simple black dining table set for two. A compact kitchen with white cabinetry and a black countertop sits in the corner, while light flows in through windows framed by exposed brick walls.
Apartment in Sarnano
4.85 out of 5 average rating, 71 reviews

In the heart of the village apartments

Take a break from the hustle and bustle of everyday life. Come and relax within the walls of the beautiful medieval center of Sarnano. Right along the staircase that leads to the main square of the town, there is this new apartment with kitchen and living room, bedroom with 2 single beds or 1 double bed and sofa bed, bathroom equipped with shower. Magnificent view of the Sibillini mountains. Great starting point for walks. Possibility to store motorcycles and recharge e-bikes nearby.

Guest favorite
A rustic stone house with a tiled roof is displayed, featuring wooden shutters and a wide entrance. A staircase leads to the upper level, while a stone barbecue area is visible to the side, surrounded by greenery and fields.
Cottage in Macerata
4.93 out of 5 average rating, 86 reviews

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.

Superhost
An indoor wellness area features a heated hydromassage minipool for six, surrounded by wide glass panels that provide views of the lush outdoor landscape and an inviting blue swimming pool beyond. Natural wood beams enhance the room's warm aesthetic.
Apartment in Gualdo
5 out of 5 average rating, 3 reviews

Agriturismo Elisei – attic, pool, sauna, spa

Are you looking for a quiet, relaxing place, surrounded by nature and away from the hustle and bustle? Do you want to discover the charm of the Monti Sibillini National Park and its villages? Choose the Elisei Farmhouse, small and for a few people, allowing each of the guests to have plenty of outdoor space. The farmhouse has a large garden with swimming pool, as well as a wellness area with sauna and spa. CIN (National Identification Code): IT043021B5CETGSYCI

Top guest favorite
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 out of 5 average rating, 42 reviews

Casale Biancopecora, Casa Cerqua

Apartment Casa Cerqua of 100 sq. meters finely furnished, we recovered all the old materials of the house in the recent renovation adapting the old farmhouse to the latest earthquake 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.

Top guest favorite
Condo in Monte San Martino (MC)
5 out of 5 average rating, 17 reviews

Room in nature with lake view - 4

Appartamenti separati che si affacciano sul lago di San Ruffino e su una bellissima vista sui Monti Sibillini. La vista sul lago è accompagnata dal suono degli animali che lo abitano e dalla natura circostante. Il luogo è un'oasi di pace: è adatto per chi è amante della natura e desidera tranquillità. Sono presenti diverse specie di uccelli ed è il luogo ideale per chi ama fotografare. L'alloggio non è dotato di cucina ma è presente un piccolo frigorifero.

Top guest favorite
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, 41 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!

Top guest favorite
The aerial view showcases the elegant Guest House surrounded by well-manicured green landscapes, vineyards, and trees. A winding gravel driveway leads to the house, highlighting its rustic charm and tranquil setting amidst the rolling hills of the Marche region.
Farm stay in Cingoli
4.98 out of 5 average rating, 84 reviews

The Guest House of the Tavignano Estate

The Tavignano estate is located in the heart of the Marche region, within the famous DOC of Verdicchio dei Castelli di Jesi, between the valleys of the river Esino and the Musone on one side, and between the Apennines and the sea on the other side. From the highest promontory of the Estate dominates the manor house, which houses the barrique, the family house, and an elegant Guest House.

Top guest favorite
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, 78 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.

Popular amenities for Penna San Giovanni vacation rentals

  1. Airbnb
  2. Italy
  3. Marche
  4. Macerata
  5. Penna San Giovanni