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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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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 in Ascoli Piceno
4.77 out of 5 average rating, 213 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.

Superhost
A well-maintained salt-water pool is surrounded by a spacious deck, featuring several sun loungers and umbrellas. The vibrant blue water reflects the evening sky, which is accentuated by soft clouds and the distant outline of mountains.
Flat in Case Alte
4.81 out of 5 average rating, 36 reviews

WONDERFUL VILLA WITH HEATED POOL IN SPRING/AUTUMN

Welcome to Anthos, our charming resort nestled in the beautiful region of Abruzzo. The property features two elegant villas that share a central swimming pool, surrounded by lush gardens full of flowers and greenery. Set in a peaceful and relaxing area, Anthos offers the perfect balance between nature and convenience – just a short drive from both the sea and the mountains. It is located within my large olive grove, in a region renowned for its world-class wines and extra virgin olive oils.

Top 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 in Servigliano
4.97 out of 5 average rating, 30 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 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.

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 in Colli del Tronto
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 in Montalto delle Marche
5 out of 5 average rating, 68 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 in Cupra Marittima
5 out of 5 average rating, 12 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
An outdoor space features a rectangular pool surrounded by wooden decking. Sun loungers are positioned nearby, with large umbrellas providing shade. The landscape includes rolling hills dotted with olive trees, vineyards, and a clear blue sky above, creating a serene atmosphere.
Flat in Controguerra
4.82 out of 5 average rating, 44 reviews

Apartment 2 Panoramic Terrace 2-4 pax

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

Top guest favourite
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.
Flat 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 good mix of modern and old, elegant but functional. Outside there is a large private area available to guests, with a shaded dining area and private barbecue. A 12x4.5 swimming pool with a shaded porch is available to guests.

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 in Montalto delle Marche
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 in Serra
5 out of 5 average rating, 30 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.

Superhost
A spacious sleeping area features a wooden bed frame topped with a patterned duvet. Two bedside tables are positioned on either side. A wooden ladder leads to a lofted space above. Soft lighting highlights the textured wall behind the bed.
Flat in Controguerra
4.66 out of 5 average rating, 98 reviews

Melissa - Relax in 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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