House holiday rentals in Ascoli Piceno

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.

4.76 out of 5 average rating, 212 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.

An inviting dining setting is showcased on a loggia, featuring a table set with plates and glasses. Two reclining chairs are positioned nearby, framed by an archway that reveals a stunning view of rolling hills and mountains in the background.

4.81 out of 5 average rating, 37 reviews

Views from the roof of Le Marche

Welcome to real Italy. This is a unique home, named locally as Casa Matita (The Pencil House). It has an awesome view awaiting you from the loggia (roofed terrace). Relax, read, drink prosecco or dine while watching amazing sunsets in the peaceful medieval village of Santa Vittoria. At the top of the hill-top village, the house enjoys a 180-degree panorama of the sea and the mountains (both 45 mins). Recently restored, with three double bedrooms, parking 50m and shops/bakery/taverna 200m.

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.

5 out of 5 average rating, 4 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.

A welcoming entrance is framed by a wrought iron awning, leading down a stone pathway bordered by lush greenery and blooming flowers. The view reveals the sparkling blue sea in the distance, enhancing the sense of an inviting coastal retreat.

4.93 out of 5 average rating, 69 reviews

Casa Belvedere

The House is located in the historic center of Colonnella, a few kilometers from the blue flag beaches of Alba Adriatica, Tortoreto, Giulianova, San Benedetto del Tronto and 26 km from Ascoli Piceno. Completely renovated with spectacular panoramic views and large terrace overlooking the Adriatic Sea. The apartment consists of a bedroom with double bed, bathroom and living room with kitchenette and double sofa bed. Bars, wineries, restaurants and supermarkets are just a short walk away.

A serene outdoor space is depicted, featuring a stone patio with seating arrangements under a canopy. Lush green trees and rolling hills are visible in the background, while a clear blue sky is adorned with fluffy clouds. A planter with flowers adds a touch of color to the scene.

5 out of 5 average rating, 22 reviews

River Garden: Relaxation just 10 minutes from the city centre

Enjoy nature 400 meters from the central square of Ascoli. You can get to the center with a walk. House with garden overlooking the river and the Papal Paper Mill. A quiet and peaceful place. You will be greeted by the warmth of the rustic environment of a typical Italian house, built by my grandfather in 1922, with exposed stone masonry. The Castellano River, which can be easily reached on foot, is perfect for a walk in any season or a cool summer swim. We look forward to seeing you!

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.

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.

A dining area features a wooden table surrounded by four chairs, complemented by a decorative table centerpiece. In the background, a spacious bed is visible through an archway, with soft, neutral-coloured walls and wooden flooring throughout the room.

4.92 out of 5 average rating, 36 reviews

La Chicca in the center - Center of Ascoli Piceno

"La Chicca in centro" is an independent house located in the historic center. Comfortable and convenient, it is located in a "rua", a small, quiet and characteristic pedestrian street of the area. A few steps from Piazza del Popolo and Piazza Arringo, the "La Chicca in centro", albeit located in a pedestrian area, is adjacent to driveways where there are paid parking lots. A large table, a kitchen and a sofa make the house an ideal space to stay even for several days.

A bright dining area is presented, featuring a round white table surrounded by four minimalist chairs. Soft natural light filters through sheer curtains, creating a serene atmosphere. A small decorative plant sits at the center of the table, while a corner floor lamp adds an inviting detail.

4.97 out of 5 average rating, 30 reviews

A stone's throw from the square

Enjoy a stylish vacation in this property in the heart of the historic center, a newly built apartment with all the services available, with a large terrace where you can relax and enjoy a snack prepared in the fully equipped kitchen. The property is completed by a beautiful double bedroom with TV and a living room with a comfortable sofa bed and reading space. In the surroundings there are all the amenities: parking and all the most beautiful monuments of the city.

A balcony view showcases rolling green hills and a clear blue sky. In the foreground, a lantern with a candle is positioned on a table, while a swimming pool is visible below, framed by manicured lawns and wooden lounging areas.

4.95 out of 5 average rating, 40 reviews

Mini apartment with pool Villa Cerqueto

The apartment, ideal for 2/5 people, consists of a large and bright living area with kitchenette, sofa bed, TV and Wi-Fi; a spacious bedroom with double bed and bunk bed and a large balcony where you can eat. The bathroom is inside the room. The swimming pool and garden are shared with all the guests of the property. The Agostini family, owner and resident of the property, will always be ready to respond to every need while respecting the privacy of its guests.

A single-story house with light green exterior sits on a gentle slope surrounded by trees. A small stone terrace is visible, providing access to the entrance. The expansive lawn features well-maintained grass and a few scattered fruit trees, contributing to the serene landscape.

4.93 out of 5 average rating, 110 reviews

"Casa Cinill" - A little slice of paradise

Take a break and unwind at this peaceful oasis. Immersed in nature, equipped with all comforts, away from the daily hustle and bustle, you can relax under the gaze of the Gran Sasso or explore the surrounding nature by walking under the trees of the forest and, with a few minutes by car, reach your favorite destinations, between the sea and the mountains to discover the wonderful Abruzzo! Large, fenced and private outdoor courtyard perfect for 4-legged friends!

A cozy living area is presented, featuring a plush red sofa and a dark brown ottoman. A classic chandelier hangs from the ceiling, and a window adorned with delicate curtains allows natural light to filter in. A television and decorative furnishings are visible in the background.

4.89 out of 5 average rating, 46 reviews

La Casetta di Dama Vacation Home

Relax with the whole family in this quiet and cozy accommodation. Located in a hilly area in an ancient village of Santa Margherita, five minutes from the Municipality of Atri, a city of Art and History. From here, in just 15 minutes, you can easily reach the beautiful beaches of Roseto and Pineto Blue Flag in the Cerrano Marine Park, and for mountain lovers, dive into the fantastic Gran Sasso Park and Monti della Laga in a short time.

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.

5 out of 5 average rating, 28 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.

Popular amenities for house rentals in Ascoli Piceno

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A stone facade of a charming house is framed by lush greenery and tall conifer trees. A gravel pathway leads to the entrance, while an iron gate adds an element of rustic elegance to the welcoming outdoor space.

5 out of 5 average rating, 7 reviews

Charming Casa Capriola - Panoramic views

New place to stay

Le Spiazzette Il Casale and the barn

A serene swimming pool is surrounded by lush greenery and vibrant trees. Comfortable lounge chairs are positioned nearby, inviting relaxation. The pool's clear water reflects the blue sky, and the setting offers a peaceful atmosphere for unwinding in nature.

4.74 out of 5 average rating, 34 reviews

Pool house, relax in the olive trees garden

New place to stay

Dolce Canto Mogliano – Farmhouse with private pool

An aerial view showcases the villa surrounded by greenery, highlighting the private pool and shaded seating areas. The building features a traditional stone exterior with a tiled roof, set against a backdrop of rolling hills and diverse vegetation.

4.9 out of 5 average rating, 10 reviews

Casa Santo Stefano, panoramic view, swimmingpool

New place to stay

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

5 out of 5 average rating, 3 reviews

Villa Aura|Exclusive retreat for families and groups

A serene outdoor area shows a fenced garden featuring a round above-ground pool. Lush trees surround the space, providing natural shade. A pathway leads from the home, which has a tiled roof, toward the pool area. The scene is bright, illuminated by clear blue skies.

5 out of 5 average rating, 17 reviews

A little house in the woods - Rustico Ceppino -

Weekly house rentals

A spacious outdoor area is surrounded by lush greenery, featuring several trees and plants. The building's modern white exterior is complemented by large glass windows. A pathway leads to the entrance, with gentle sunlight illuminating the scene under a clear blue sky.

4.95 out of 5 average rating, 37 reviews

House of Olives

A single-story house is set within a landscaped garden, featuring a grassy area and neatly trimmed hedges. The building showcases a rustic stone façade, a tiled roof, and multiple windows. Comfortable outdoor seating is visible on the patio, surrounded by lush greenery and palm trees.

4.98 out of 5 average rating, 46 reviews

TYPICAL HOUSE IN SMALL VILLAGE

A rustic stone building is framed by lush green foliage, showcasing a charming balcony above the entrance. The sun illuminates the scene, highlighting the texture of the stone walls and the peaceful surroundings.

4.92 out of 5 average rating, 38 reviews

Casa Vacanze Gli Allori

4.82 out of 5 average rating, 17 reviews

Casa Marina

A bright and airy kitchen area is presented, featuring a small dining table with four black chairs. A kitchenette is equipped with essential appliances, including a stove and a kettle. Natural light enters through a glass door, which leads to a balcony draped in white curtains.

4.77 out of 5 average rating, 145 reviews

Apartment with View of the Sibillini Mountains and Hamlet

A minimalist balcony area is highlighted, featuring a smooth stone bench and an ornate planter. The railing is adorned with intricate ironwork, providing a view of the surrounding architecture under a clear blue sky.

4.91 out of 5 average rating, 46 reviews

Terraces overlooking the village

A well-lit entryway features terracotta tile steps leading to a wooden door adorned with wrought iron. A small seating area is visible, accompanied by a table set for dining. Natural light fills the space, highlighting the clean, minimalist decor.

4.98 out of 5 average rating, 43 reviews

Central House near the Sferisterio

A spacious villa is surrounded by lush greenery and mature palm trees. An inviting swimming pool is complemented by sun loungers on a wooden deck. The property is nestled among rolling hills, creating a serene and private outdoor setting.

4.71 out of 5 average rating, 17 reviews

Villa Iulia | VIBRA

Private house rentals

A serene outdoor space is framed by tall, leafy trees, providing shade over white lounge chairs positioned on the grassy area. In the background, a charming residence is visible, with rolling hills extending beyond.

5 out of 5 average rating, 7 reviews

La Terrazza dei Monti Azzurri

A two-story orange house is surrounded by greenery, featuring a gravel pathway leading to the entrance. Tall trees and shrubs are scattered around the property, providing a natural setting. A covered area can be seen in the background, adding to the outdoor appeal.

4.89 out of 5 average rating, 9 reviews

House in the Marche countryside

A cozy living area features a rustic stone wall and dark wooden beams overhead. A chandelier provides ambient lighting. A blue sofa sits beside a small table, with a comfortable armchair nearby. A window offers a view of the surrounding landscape.

4.67 out of 5 average rating, 3 reviews

Casa Elsa – Monti Sibillini National Park

The exterior of the house features a modern, white facade with large windows and a clear entrance. A well-maintained green lawn surrounds the property, complemented by decorative plants. An adjacent covered area offers seating options, and parked vehicles are visible in the driveway.

4.96 out of 5 average rating, 25 reviews

country house

5 out of 5 average rating, 8 reviews

La Finestra sul Castello | Elegance and comfort

A charming entrance is framed by lush greenery, featuring a green door with a decorative ornament. Bright yellow walls create a cheerful backdrop, while a brick wall adds rustic appeal. The upper-level balcony is adorned with a flower box, inviting nature into the design.

5 out of 5 average rating, 20 reviews

La Roverella, a house in the countryside

A cozy sleeping area is presented with a spacious bed featuring a plaid blanket. The headboard is upholstered and complemented by soft, warm lighting positioned on either side. Exposed stone walls add a rustic charm to the room.

4.83 out of 5 average rating, 47 reviews

The Dimora del Cont'Orto

A single-story house is set against a backdrop of green grass and trees. The exterior features a tiled roof and stone detailing. Wooden shutters cover the windows, and a stone path leads to the entrance. The open area invites natural light and fresh air.