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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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Top guest favorite
The Villa is set among olive trees, featuring a tranquil saltwater pool surrounded by lounge chairs. A stone terrace offers shaded seating, and the rustic building showcases large windows and natural materials. The expansive grounds create an inviting space for relaxation and leisure.
Home in Spello
5 out of 5 average rating, 17 reviews

Villa degli Olivi

Nestled among the ancient olive trees, Villa degli Olivi offers a haven of serenity and sophistication and is a short stroll into the cobblestoned paths of Spello along a flat, tree lined lane. This recently renovated Villa offers modern luxury while maintaining its Italian roots. Offering 4 bedrooms, 3 full baths and the possibility for 2 additional guests with a sleeper sofa. A cozy studio apartment with full kitchen, bathroom, laundry and sleeper sofa is also available for an additional cost.

Top guest favorite
The Sferisterio theater is highlighted by its grand brick colonnade, illuminated against a dusk sky. The curved structure features multiple seating levels with historic elements and a vibrant atmosphere, showcasing an audience gathered in anticipation of the evening performance.
Apartment in Mogliano
4.94 out of 5 average rating, 34 reviews

Opera & Nature Lovers Loft Suite 30 mins 2 Opera

Located in the heart of Le Marche—ranked 2nd in Lonely Planet's 2020 list of "The Top 20 Regions in the World to Visit"—this sunny apartment offers the perfect base to relax or explore. Just 30 minutes from the world-renowned open-air opera venue, the Sferisterio in Macerata, and within an hour to mountains, lakes, and the sea. Discover ancient hilltop towns, nature reserves, outdoor markets, health spas, and scenic hiking, biking, and riding trails. 5 mins’ drive to the village of Mogliano.

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
4.81 out of 5 average rating, 37 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
A serene pool area is featured, with crystal-clear water reflecting the surrounding greenery. The rustic stone buildings in the background are framed by lush trees, while comfortable seating arrangements invite relaxation under the sun.
Casa particular in Matelica
4.91 out of 5 average rating, 22 reviews

I light up with immense

Enjoy a different vacation and regenerate your body and mind. Bring books to read under the mulberry trees. Walk through nature, breathing healthy air and traveling kilometers of countryside with organic crops while observing the landscape where nature has been able to create paintings. Relax with the whole family, living days with a different spirit and more attention to those close to you, in accommodation where serenity, atmosphere and nature make everything wonderfully unique.

Guest favorite
Home in Spello
5 out of 5 average rating, 18 reviews

Wellness Grotto & Panoramic View | Lucy's House

• A unique retreat in the heart of Spello • Unwind in the private panoramic courtyard with hot tub, outdoor fireplace, and the silent Umbrian valley stretching out before you. Step inside, light the fireplace, and descend into your private wellness grotto: infrared sauna and chromotherapy hydromassage tub, for your exclusive use throughout your entire stay. No timetables, no other guests. Just you. 🫧 Full exclusive access to the wellness grotto is included with every booking 🫧

Superhost
Home in Belfiore
5 out of 5 average rating, 3 reviews

Casale del Menotre | Countryside Umbrian Retreat

Just minutes from Assisi, between Rasiglia, Spello, and the Menotre Waterfalls, the tourist rental welcomes you. After a day discovering Umbria, just relax in the hydromassage, hammock, deckchairs and BBQ area immersed in nature and the silence of the Umbrian landscape. The house has Wi-Fi, Smart TV with access to personal Netflix, air conditioning and 3 bedrooms, one of which has a private bathroom. Non-entrepreneurial tourist rental without additional services.

Guest favorite
An aerial view showcases the agriturismo's rustic stone buildings surrounded by greenery. A blue swimming pool is located in the garden, complemented by sun loungers. The landscape features open fields and scattered trees, creating a serene outdoor space.
Apartment in Gualdo
5 out of 5 average rating, 7 reviews

Agriturismo Elisei – apartment, 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

Guest favorite
Condo in Monte San Martino (MC)
5 out of 5 average rating, 15 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 welcoming stone retreat is set against a lush green hillside. A modern chair is positioned by a clear swimming pool, reflecting the vibrant outdoor scenery under partly cloudy skies.
Farm stay in Cellino Attanasio
5 out of 5 average rating, 15 reviews

Country Escape - Pool & Hot Tub

Escape to our charming retreat in the heart of Abruzzo, ideal for couples seeking romance or a small family getaway. Perfectly positioned between the sea and the mountains, our home offers stunning natural surrounds. Enjoy exclusive outdoor amenities: a refreshing pool, relaxing hot tub, cozy firepit, and al fresco dining area. Engage with nature and meet our friendly farm animals—goats, chickens, ducks, cats, and our lovable dog.

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.

Popular amenities for Penna San Giovanni vacation rentals

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