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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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Guest favourite
Flat
5 out of 5 average rating, 11 reviews

ROMANTIC 7 BEDS APARTMENT WITH POOL

If you're looking for a holiday surrounded by nature, relaxation, great food, and the joy of slow living – this is the place for you! Just minutes from the sea and nestled in the greenery of a scenic hillside, our independent apartment offers fresh air, peace, comfort, and breathtaking views. The atmosphere is welcoming and well cared for – perfect for those who truly want to unwind. Outside, a beautiful saltwater pool, heated in spring and autumn – ideal for a refreshing swim in every season.

Top guest favourite
A serene infinity pool is set against a backdrop of rolling hills and a clear blue sky. Wooden lounge chairs are positioned beside the pool area, offering space for relaxation. The wooden deck surrounds the pool, complementing the natural landscape.
Flat
5 out of 5 average rating, 45 reviews

House with swimming pool, ground floor, Villa Cerqueto

Apartment in a house with a swimming pool in the hills 20 km from the sea. Equipped with all the comforts to spend 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.

Superhost
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, 217 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.

Guest favourite
A dining area features a white table set for breakfast, positioned under arches that frame views of rolling hills and a swimming pool. Sunlight filters through an open window, enhancing the serene outdoor scenery.
Home
5 out of 5 average rating, 8 reviews

Large family apartment at Villa Milli

Relax with the whole family in this quiet accommodation. It opened in July 2018 after a careful renovation of an old country house. In the hills, between the Adriatic Sea and the Gran Sasso. Ideal for those seeking relaxation, tranquility and want to discover the beauty of Abruzzo. In just 15 minutes, you can reach Giulianova Beach The farmhouse is divided into 4 apartments, a large park of 80 square meters, a swimming pool, and a barbecue area. The apartment is on the second floor.

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.

Top guest favourite
A kitchen area with rustic wooden cabinets and a white refrigerator is depicted. A dining table made of wood, surrounded by white chairs, occupies the center. Natural light enters through large windows, illuminating the stone walls and creating a warm, welcoming environment.
Home
5 out of 5 average rating, 41 reviews

Casale Biancopecora, Casa Ghianda

Independent house in Country House, Casa Ghianda, 60 sqm finely furnished. We recovered all the old house materials in the recent renovation. One of the rooms overlooks a small terrace. Outside there is a large private area available to guests, shaded pergola and private barbecue. Complete the property with a 12x4.5 pool with shaded porch available for guests to enjoy.

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