Vacation rentals in Gualdo

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Top-rated vacation rentals in Gualdo

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Villa in Castelraimondo

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.

LocationFamilyOutdoor spaces

4.82 out of 5 average rating, 11 reviews

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

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.

LocationFamilyNearby

5.0 out of 5 average rating, 8 reviews

Villa in Gualdo

La casa di Iole

Distesa su una collina ,la nostra casa vacanze offre una vista mozzafiato dei monti sibillini. Il giardino e la piscina sono pensati per il relax ed il divertimento dei più piccoli. Per gli amanti dell’avventura, il Parco Nazionale dei Monti Sibillini offre sentieri per trekking e mountain bike, mentre in 20 minuti raggiungerete il Lago di Fiastra. Se amate il mare, le spiaggie sono raggiungibili in 45 minuti in una strada panoramica tra le colline. A solo un'ora circa da Assisi e Perugia.

LocationComfortOutdoor spaces

5.0 out of 5 average rating, 3 reviews

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

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.

FamilyLocationView

4.87 out of 5 average rating, 82 reviews

Guest favorite

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

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.

FamilyLocationAmenities

4.98 out of 5 average rating, 45 reviews

Guest favorite

The image captures a scenic view of La Roccaccia, featuring a private pool and lush greenery. Stone pathways meander through the garden, with tall cypress trees framing the scene, while a historic tower is visible in the background against a clear blue sky.

Castle in Montefortino

MarcheAmore - La Roccaccia, La Sibilla Apartment

La Roccaccia was built in 1080 AD as a lookout tower to defend the Fermo area. Located in an enchanting setting between Monte Sibilla, the gorge of Infernaccio and the hilltop town of Montefortino. Today La Roccaccia is a luxury venue with private pool and jacuzzi located among the Sibillini mountains, designed for those in search of peace, relaxation and meditation. Its park is filled with works of art and at it features a private amphitheater with a unique view.

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 7 reviews

An aerial view showcases the villa surrounded by greenery, highlighting the private pool and shaded seating areas. The building features a traditional stone exterior with a tiled roof, set against a backdrop of rolling hills and diverse vegetation.

Home in Gualdo

Casa Santo Stefano, panoramic view, swimmingpool

Casa Santo Stefano is a unique location if you want to relax. The villa is located at the foot of the world-famous Sibillini Mountains at 650m altitude. On private grounds of more than 10,000m2, you will find yourself in an oasis of peace and enjoy the breathtaking rolling valley and the Sibillini Mountains. You can choose to do nothing at all and drink an espresso at the private pool, but if you want a more active vacation, there are plenty of options. Be welcome!

FamilyLocationHiking

4.88 out of 5 average rating, 17 reviews

Guest favorite

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

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

LocationOutdoor spacesHospitality

5.0 out of 5 average rating, 7 reviews

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

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!

LocationFamilyHospitality

4.98 out of 5 average rating, 42 reviews

Guest favorite

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

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.

LocationFamilyAccuracy

4.94 out of 5 average rating, 35 reviews

Top guest favorite

Villa in Sant'Angelo in Pontano

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.

LocationFamilyPool

5.0 out of 5 average rating, 5 reviews

Top guest favorite

A wooden cabin is surrounded by lush greenery and wildflowers, showcasing a welcoming entrance and large windows. The sunlight highlights the natural colors of the exterior, creating a serene atmosphere in harmony with the surrounding landscape.

Tiny home in Sarnano

Montequieto: peace and nature by the Sibillini.

Located just outside Sarnano, Montequieto is a wooden cottage nestled in nature, with breathtaking views of the Sibillini Mountains. Ideal for relaxing, exploring the surrounding trails, venturing into the unspoiled landscapes of the Monti Sibillini National Park or discovering the medieval village of Sarnano, one of the most beautiful in Italy.

LocationDecorHospitality

5.0 out of 5 average rating, 21 reviews