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Holiday rentals in Monteprandone

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Top-rated holiday rentals in Monteprandone

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A softly lit bedroom features a spacious bed with a patterned headboard and relaxed bedding. A bedside table supports a lamp, providing additional light. A closet with wooden doors adds functional elegance, while an open door leads to a more private area of the apartment.
Apartment in San Benedetto del Tronto
4.91 out of 5 average rating, 170 reviews

[Brand New-Pedestrian Area] Lovely Apartment

Brand new apartment, in a historic building, elegantly furnished with designer furniture and components. Style, functionality and the characteristic attic structure make the environment graceful, welcoming and suitable for travelers from around the world. Located in a Super Central position, in the heart of the Pedestrian Island, just 5 minutes from the sea and the suggestive “Riviera delle Palme” promenade. A strategic location whether you are in S. Benedetto T. on vacation, for business or pure leisure.

Guest favourite
A well-appointed dining area features a wooden table surrounded by four chairs, complemented by a bouquet of flowers. An open kitchen with modern appliances is visible, and a cozy sitting area with a sofa is situated beside a staircase leading to a loft space.
Flat in Monteprandone
4.86 out of 5 average rating, 35 reviews

Sole apartment

Nice apartment located on the second floor of a historic building in the center of Monteprandone. Apartment with a mezzanine where the double bedroom is located, in the lower part there is the dining area/kitchen, the living area with the sofa bed and a bathroom. The house is located 6 km from the beautiful promenade of San Benedetto del Tronto, a few km from Ascoli Piceno with its artistic beauties, as well as from numerous characteristic hill towns also famous for their gastronomic delicacies.

Guest favourite
A picturesque scene showcases the vast outdoor space leading toward majestic snow-capped mountains. A path is lined with trees and shrubs, while a rustic building is visible in the distance. The clear blue sky provides a bright backdrop to the tranquil landscape.
Cottage in Isola del Gran Sasso d'Italia
4.91 out of 5 average rating, 55 reviews

Lovely cottage by the Gran Sasso mountain.

La Casetta di Trignano. Really close to the mountain (for those who love hiking), to the Sanctuary of San Gabriele and 40 minutes from the seaside and the Adriatic coast. 1h from Pescara, 2h from Rome Airports by car or bus. The structure, fully fenced, has got a private entrance, 3 car places, a patio with table and chairs in the private garden, a vegetable garden and a small orchard. Two bedrooms each with a private bathroom, kitchen, dining room with sofa-bed and fireplace, extra bathroom.

Top guest favourite
Home in Penne
5 out of 5 average rating, 12 reviews

3 Bedroom home, Private Pool, HotTub&Home Theater

Casa Fenice is located next to an olive grove and overlooking the cultivated fields of neighboring farms. Across the valley of the Saline River you will see the vineyard of San Lorenzo wines, the medieval villages of Elice and Castilenti, and small suburbs with support businesses for the farmers in the area. The nearest neighbor is 200m away, so with the exception of the occasional friendly farmer on his tractor, you are able to enjoy the blissful peacefulness of country living.

Guest favourite
Villa in Colli del Tronto
5 out of 5 average rating, 9 reviews

Frescoes and Centuries-Old Park– Villa Mastrangelo

Well-known residence in our area You can easily find us online as a local tourist landmark. 1️⃣ Self check-in available at any time 2️⃣ Discounts for longer stays (contact me for details) 🏰 Entire villa of over 600 m² 🌿 Centuries-old park of 2000 m² – pet friendly 🚗 Private parking, both open and covered – free of charge 📶 Air conditioning, fast Wi-Fi and Smart TV ☕ In the kitchen: coffee, tea, oil, vinegar, sugar, salt, etc. 🧺 Bed linen, towels and soap included

Guest favourite
A rustic stone house with a tiled roof is displayed, featuring wooden shutters and a wide entrance. A staircase leads to the upper level, while a stone barbecue area is visible to the side, surrounded by greenery and fields.
Cottage in Macerata
4.93 out of 5 average rating, 81 reviews

The house in the old granary

The country farm, surrounded by olive trees and centuries-old oaks, will be all for you just 25 minutes from the sea and an hour from the Sassotetto ski slopes. Ideal for couples or families looking for relaxation, our house is immersed in a silence of yesteryear. You are a 10-minute drive from Macerata and half an hour from the beaches. The space will be at your exclusive disposal. We have a Home Theater with HiFi system. A wood-burning oven is available upon request.

Top guest favourite
A modern structure is positioned harmoniously within a natural landscape. The exterior showcases a combination of stone and smooth surfaces, complemented by expansive windows that allow for views of the surrounding greenery and mountains.
Home in Fonte Cerreto
4.98 out of 5 average rating, 224 reviews

Cocoon of Gran Sasso

"O blessed solitude, or only bliss" Immersed in the tranquility of nature and a few meters from the Annorsi Fountain and its precious spring water, the "Gran Sasso Refuge" was a stable for sheep. After years of abandonment, converted to residential and accommodation use, it found a second life thanks to a wise renovation that, while respecting the context, made use of the latest technologies such as the floor heating system or the ventilated roof structure

Top guest favourite
A peaceful exterior view showcases a charming house with a covered patio. The garden features seating for two and is adorned with flowering plants. Expansive hills and fields create a serene backdrop, with soft clouds reflecting light across the sky.
Home in Montefiore dell'Aso
4.98 out of 5 average rating, 66 reviews

La Casetta - tranquility between the sea and the mountains

Immersed in the greenery, among the hills of Val Menocchia, stands 'La Casetta', a small and charming independent house, recently renovated. Perfect for those who want to spend a relaxing holiday and enjoy the landscape that surrounds it. However, it adapts to all needs: it is located a few kilometers from the sea and at short distance from wonderful villages, it also allows mountain lovers to reach the Sibillini Mountains in just over an hour.

Top guest favourite
Holiday home in Grottammare
4.96 out of 5 average rating, 75 reviews

Casita del Mar Romantic loft 250m walk to the sea

Just 250 meters walking distance from the sea, Casita del Mar is a retreat where time slows down. An intimate and thoughtfully designed artistic loft, where light, wood and details create a warm and authentic atmosphere. Here, you don’t just stay — you experience: the sound of the sea, a sunset, a moment just for yourself. More than accommodation, it’s an emotion to live. Our dream is simple: to create emotions.

Guest favourite
A cozy living area features a modern grey sofa and a dining table set for meals. A 65-inch LED TV is mounted on the wall, complemented by decorative elements. Natural light floods in through the open balcony door, which leads to a patio with greenery.
Flat in Martinsicuro
4.96 out of 5 average rating, 48 reviews

ALGA- 5 Star Boutique Apartment Steps from the Sea

Looking for your home away from home in Martinsicuro? Meet Alga. Whether you’re in town for business meetings or a family vacation, you’ll enjoy a 5-star stay where you can relax and recharge your batteries. IDEAL for business professionals and small families who want to relax in style. **TRAVELING WITH A GROUP?** If you’re traveling with a larger group, be sure to check out our listing for Stella next door!

Guest favourite
The rustic stone exterior of the retreat is highlighted by warm evening light. A modern building stands alongside a landscaped area featuring lounge furniture. Lush greenery surrounds the property, enhancing the tranquil setting.
Farm stay in Cellino Attanasio
5 out of 5 average rating, 11 reviews

Hideaway with pool and hot tub

Discover our charming retreat in Abruzzo, perfect for families or friends. Nestled between mountains and sea, our home features stunning views and superb outdoor amenities: a pool, hot tub, firepit, and dining area. Enjoy nature and meet our friendly farm animals. Ideal for up to four guests looking for a memorable escape.

Guest favourite
A spacious open-plan living area is highlighted by large windows offering panoramic sea views. A white sectional sofa is positioned near a sleek pool table, while a dining table with chairs is visible in the background. Natural light fills the space, enhancing the modern decor.
Flat in Civitanova Marche
4.94 out of 5 average rating, 16 reviews

[Luxury Seafront Penthouse] Parking & Beach

Property managed by Host Hero Marche Welcome to our exclusive penthouse on the sixth floor of a recently built building, located in a privileged position along the seafront of Civitanova Marche. This apartment offers breathtaking sea views and unparalleled comfort, making it perfect for a relaxing and rejuvenating vacation.

Popular amenities for Monteprandone holiday rentals

  1. Airbnb
  2. Italy
  3. Marche
  4. Ascoli Piceno
  5. Monteprandone