
Holiday rentals with a pool in Ascoli Piceno
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Top-rated rentals with a pool in Ascoli Piceno
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.
4.74 out of 5 average rating, 219 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.
5.0 out of 5 average rating, 8 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.
4.97 out of 5 average rating, 34 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.
4.79 out of 5 average rating, 39 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.
4.86 out of 5 average rating, 35 reviews
Casale Biancopecora, Casa Cerqua
Apartment Casa Cerqua of 100 square meters finely furnished, we have recovered all the old materials of the house in the recent renovation by adapting the old farmhouse to the latest anti-seismic regulations. The decor is a right mix of modern and ancient, elegant but functional. Outside there is a large private area available for guests, with shaded dining area and private barbecue. Complete the property with a 12x4.5 pool with shaded porch available for guests to enjoy.
5.0 out of 5 average rating, 45 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.
5.0 out of 5 average rating, 73 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.
5.0 out of 5 average rating, 15 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.
4.83 out of 5 average rating, 47 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!!
4.95 out of 5 average rating, 19 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.
4.94 out of 5 average rating, 35 reviews
Borgo Seghetti Panichi, 'Lotto' Apartment
Dedicated to the artist Lorenzo Lotto, this suite features a spacious living room on the ground floor with a large sofa bed and a kitchen equipped with essential amenities, with an adjoining dining table. Upstairs is the double bedroom with a marble travertine bathroom, decorated with green and cream wallpaper and furnished with walnut furniture. The apartment has a television and Wi-Fi.
5.0 out of 5 average rating, 3 reviewsPopular amenities for Ascoli Piceno rentals with a pool
House rentals with a pool

Large family apartment at Villa Milli
5.0 out of 5 average rating, 10 reviews
Fonte del Ceppo 2 by Interhome
5.0 out of 5 average rating, 3 reviews
Villa Irma with Pool 10 min from the Sea - over 8 Y

{Private Pool} 10 beds, Wifi, AC, Garden

Charming Casa Capriola - Panoramic views
5.0 out of 5 average rating, 10 reviews
Villa Ophite: 3 bedrooms and pool
5.0 out of 5 average rating, 12 reviews
Casa Santo Stefano, panoramic view, swimmingpool
4.88 out of 5 average rating, 17 reviews
La Rocciosa with swimming pool. Breathe in the Sibillini.
5.0 out of 5 average rating, 3 reviewsApartment rentals with a pool

Lavender - Relax in the vineyards of Abruzzo
4.82 out of 5 average rating, 33 reviews
Domus Petrae - Oca Apartment
5.0 out of 5 average rating, 3 reviews
Villa La Passione - Entire King flat with pool
5.0 out of 5 average rating, 9 reviews
Cossignani Farmhouse La Terrazza apartment
5.0 out of 5 average rating, 4 reviews
Colle della Sibilla – Country Flat
4.9 out of 5 average rating, 31 reviews
Il Piccolo Carro - Girasole Apartment
4.8 out of 5 average rating, 15 reviews
Apartment – IL Villaggio del RE Residence
4.53 out of 5 average rating, 15 reviews
il borghetto with pool
5.0 out of 5 average rating, 4 reviewsOther holiday rentals with a pool

L'Attico Sul Fiume center home
4.91 out of 5 average rating, 199 reviews
The Cherry House, apt Geranio
4.95 out of 5 average rating, 20 reviews
Villa Fonte in Colle Exclusive relaxation in the Marche region
5.0 out of 5 average rating, 13 reviews
MarcheAmore - La Roccaccia, La Sibilla Apartment
5.0 out of 5 average rating, 7 reviews
NEW! Charming farmhouse retreat with private pool
5.0 out of 5 average rating, 12 reviews
Lemonvilla - Panoramic position - Pool - 240sqm
4.96 out of 5 average rating, 25 reviews
Cantina Le Canà - Quies apartment
4.98 out of 5 average rating, 82 reviews
Family villa,pool,hilltop, sea Wi-fi Air-co EV cha
4.9 out of 5 average rating, 10 reviewsDestinations to explore
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- Rentals with pools Marche
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- Riviera del Conero
- Terminillo
- Rocca Calascio
- Gran Sasso d'Italia
- Monte Terminillo
- Monte Terminilletto
- Frasassi Caves
- Pescara Centrale
- Sibillini Mountains National Park
- Spiaggia Urbani
- Sibillini Mountains
- Shrine of the Holy House
- Sirolo
- Mount Subasio
- Birthplace of Gabriele D'Annunzio Museum
- Spiaggia della Torre
- Fonti Del Clitunno
- Centro Commerciale Megalò
- Sirente Velino Regional Park
- Stiffe Caves
- Torre Di Cerrano
- Spoleto Cathedral
- Lame Rosse
- Eremo delle Carceri
- Things to do Ascoli Piceno
- Things to do Marche
- Cooking Marche
- Outdoors Marche
- Cultural tours Marche
- Food tours Marche
- Tastings Marche
- Things to do Italy
- Workouts Italy
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- Cooking Italy
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