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Holiday rentals with a pool in Ascoli Piceno

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ascoli Piceno

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
The image captures rolling hills adorned with lush greenery and vineyards, extending towards the horizon. A quaint stone structure is visible in the foreground, complemented by wooden fencing and a clear blue sky. The serene landscape reflects the natural beauty of the Marche region.
Flat
4.98 out of 5 average rating, 42 reviews

Casale Biancopecora, Casa Sanforte

We are located in the south of the Marche near Fermo and Ascoli Piceno, among the olive trees and the organic vineyard of Casale Biancopecora di Massimo and Michela, a fully recovered structure with principles of construction and anti-sismic, the views as far as the eye can see in the wonderful countryside of central Italy and the Sibillini Mountains. Just 27 km from the sea of Porto San Giorgio. The apartments have been renovated using the original old materials of the house with all the current comforts.

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Flat
5 out of 5 average rating, 3 reviews

Borgo Seghetti Panichi, 'Sibilla' Apartment

A spacious first floor self-catering apartment in the old farmhouse of the Borgo Storico Seghetti Panichi, our family home with a historic villa and chapel, surrounded by a celebrated romantic 1870s garden. Guests can enjoy the garden, pool, citrus terraces, olive grove, kitchen garden, wildflower meadow and shaded seating areas. The view sweeps from the sea to the high Apennines. Sandy Adriatic beaches and fine seafood are 20 mins away; the renaissance jewel of Ascoli Piceno is even closer.

Superhost
An aerial view showcases a private poolside area surrounded by lush greenery and a well-maintained patio. The inviting pool displays crystal-clear water, with a small seating area near the edge. A charming house with a wooden exterior is visible, enhancing the tranquil ambiance.
Home
4.75 out of 5 average rating, 216 reviews

La Casetta - Entire house 5 minutes from the center.

Your Oasis of Relaxation in the Marche Region The CASETTA is a cozy home located in the open countryside, just minutes from the historic city of Ascoli Piceno. Surrounded by a lush and unspoiled agricultural landscape, it offers guests a stay experience that combines modern comfort with the authentic atmosphere of the Marche countryside. Thanks to its strategic location, it is the ideal starting point to explore the historic center, the mountains and the sea, all within a few minutes' drive.

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
4.97 out of 5 average rating, 31 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.

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
5 out of 5 average rating, 6 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.

Superhost
The two-story farmhouse features a spacious lawn framed by bare trees. A covered pergola extends from the house, providing a shaded area with seating beneath it. Wooden shutters adorn the upper windows, while the exterior is highlighted by a warm brick facade.
Home
4.85 out of 5 average rating, 34 reviews

Corner of paradise - Alpaca village nature and relaxation

Typical Marche farmhouse on two floors with a fabulous pergola overlooking the garden. The house is 1 km from the center of the village. Immersed in the Marche countryside, the house is located a few meters from the Tronto river and bordering the bike path that connects S. Benedetto. Not having houses in the immediate vicinity, the house allows you to fully enjoy your stay in absolute freedom (even with music until late at night). A barbecue and wood-burning oven are available.

Top guest favourite
An infinity pool is set against a panoramic landscape, showcasing rolling hills and a clear blue sky. Comfortable lounge chairs are positioned nearby on a wooden deck, inviting relaxation while enjoying the serene views.
Flat
5 out of 5 average rating, 69 reviews

House with pool, 1st floor, Villa Cerqueto

Located on the 2nd floor and ideal for 6/7 people. Equipped with all the comforts to enjoy a peaceful vacation in contact with nature and the beauty of the landscape among typical villages, the Adriatic Sea and the Sibillini Mountains. The apartment has 2 large air-conditioned bedrooms, 1 bathroom and 1 kitchen with a terrace where you can eat. The garden and swimming pool, shared with other guests, enjoy a privileged position from which you can enjoy a beautiful view.

Guest favourite
A private above-ground pool is situated on a spacious deck with blue railings, overlooking the sea. An area for children's play can be seen nearby, with a sandy surface. The surrounding landscape features hills and greenery against a clear sky.
Home
5 out of 5 average rating, 13 reviews

The Goddess Terraces Cottage

Villa with above-ground pool located on the first hill close to the sea. The property can be reached from the sea by following an uphill road of 600 meters. The 144-square-meter house consists of a living room with a kitchenette. In this room there is a sofa bed and a bunk bed. In the sleeping area there are 3 bedrooms (double, medium with double bed and single with bunk bed + additional bed), bathroom with bathtub and bathroom with shower.

Superhost
A refreshing outdoor pool is surrounded by a wooden deck and white lounge chairs. Lush trees and an open landscape featuring rolling hills and vineyards are visible in the background, along with a clear blue sky.
Home
4.79 out of 5 average rating, 56 reviews

Apartment 1 Panoramic Terrace 2-3 Pax

The farmhouse, renovated in rustic style with exposed bricks is set in a landscape between rows of vineyards and extensive olive groves. The apartment with wooden roof and a large terrace overlooking the Montagne Gemelle, the Gran Sasso, and the Monti Sibillini. You will enjoy the quiet of the countryside in a true slice of agricultural life. We are inside a winery, it is possible, on request, to buy wine or book a themed tasting.

Guest favourite
A tranquil outdoor view displays a charming rural property surrounded by lush greenery and scenic hills. A private pool sits centrally, accompanied by sun loungers and umbrellas. The well-maintained pathway leads towards the main house, showcasing rustic architecture under a clear blue sky.
Farm stay
4.94 out of 5 average rating, 18 reviews

Regina Apartment

The Regina apartment of the Terre Vineate Farmhouse consists of a large living room with kitchenette, two bedrooms with bathroom inside. The two bedrooms have air conditioning. Outside, it has a small reserved wooden gazebo. You can take advantage of the common areas such as the central porch overlooking the Sibillini, the swimming pool, the children's play area and the cellar. We look forward to seeing you!!

Top 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
4.94 out of 5 average rating, 34 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.

Guest favourite
An open-plan living area features a dining table with green chairs, a sofa, and a bed against the wall. A television is set on a wooden unit, and a white refrigerator stands nearby. Natural light fills the room through a window and a skylight.
Flat
4.94 out of 5 average rating, 77 reviews

Salvia - Relax among the vineyards of Abruzzo

In a completely renovated old 19th-century farmhouse, surrounded by olive groves and vineyards, 15 minutes from the SEA, we offer an independent apartment, swimming pool area (open only in summer), a barbecue, Turkish bath, Thai massage (subject to availability) and a soccer field.

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