
Holiday rentals with a pool in Ascoli Piceno
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Top-rated rentals with a pool in Ascoli Piceno
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Sunrise, Sunset, Swim – Live the View Every Day
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.

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.

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.

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.

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.

A little house in the woods - Rustico Ceppino -
Surrounded by greenery, you can relax with the whole family in this quiet, exclusive-use accommodation. The house is completely isolated just 500 meters from the small village and 2 km from the Roccaforte di Civitella del Tronto. Away from the hustle and bustle, you can enjoy the beautiful landscape, lie on the lawn to sunbathe, take a dip in the pool or gaze at the stars. Light a fire for the barbecue and eat outdoors. These are just some of the things you can do in our cottage.

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.

La Betulla - Majesty View LUX
Escape to an exclusive 4-bedroom luxury villa set within 25,000 sqm of breathtaking landscapes in the heart of Italy. Perfect for those seeking relaxation, adventure, and gourmet experiences. ✨ Why You’ll Love It: 🌿 Truffle Forest & Farm Lab 🏊♂️ Expansive Pool & Outdoor Lounge - Unwind in pure luxury 🛏️ Elegant & Spacious Interiors 🌍 Prime Location – Close to the Adriatic Coast & top cultural destinations Book now for a one-of-a-kind Italian escape! 🌟

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.

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.

Casale Biancopecora, Casa Acorn
Detached house in Country House, House Acorn, 60 sqm finely furnished. We recovered all the old materials from the house in the recent renovation. One of the rooms overlooks a small terrace. Outside there is a large private area available for guests, shaded pergola and private barbecue. The property is completed by a 12x4,5 swimming pool with shaded porch available for guests.

Villa Adele
Welcome to Villa Adele, a residence immersed in the quiet and greenery of the Abruzzo hills, located on a private street in the characteristic village of Ripattoni, a hamlet of the municipality of Bellante (Teramo). An ideal solution for those looking for relaxation, space and comfort in an authentic and regenerating environment.
Popular amenities for Ascoli Piceno rentals with a pool
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NEW! Charming farmhouse retreat with private pool
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- Riviera del Conero
- Terminillo
- Rocca Calascio
- Frasassi Caves
- Gran Sasso d'Italia
- Sibillini Mountains National Park
- Pescara Centrale
- Monte Terminilletto
- Shrine of the Holy House
- Monte Terminillo
- Spiaggia Urbani
- Sibillini Mountains
- Mount Subasio
- Sirolo
- Birthplace of Gabriele D'Annunzio Museum
- Torre Di Cerrano
- Spoleto Cathedral
- Stiffe Caves
- Sirente Velino Regional Park
- Centro Commerciale Megalò
- Porto Turistico Marina Di Pescara
- Spiaggia di San Michele
- Fonti Del Clitunno
- Spiaggia della Torre
- Things to do Ascoli Piceno
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- Food and drink Marche
- Entertainment Marche
- Nature and outdoors Marche
- Art and culture Marche
- Things to do Italy
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