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Holiday houses in Monteprandone

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Top-rated holiday rentals in Monteprandone

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious terrace is showcased with a table and a chair set against a sunlit wall. A potted plant sits prominently, adding greenery to the space. Nearby buildings create a backdrop, while the surrounding area suggests a peaceful outdoor setting.
Apartment in San Benedetto del Tronto
4.94 out of 5 average rating, 54 reviews

At the terrace of San Benedetto, paradise exists!

Everything for you, 80 sqm penthouse, clean, bright and quiet, with panoramic terrace, close to everything: sea (6 min. walk), shops (3 min), station and pedestrian center of S. Benedetto (15 min. walk), with A/C, wifi, free parking NOT reserved; including bed and bath linens (see Included Services) NOTES: ¤ Check-out by 10 a.m. and check-in after 3 p.m. ¤ 1 single attic room, without door ¤ Elevator up to 3rd floor, stairs from 3rd to 4th floor penthouse ¤ Non-windowed bathroom with exhaust fan

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.
Apartment 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.

Top Guest favourite
An outdoor patio area features a soft seating arrangement, illuminated by string lights. Large umbrellas provide shade over the lounge space, while an infinity-edge pool reflects the night sky. The surrounding landscape is visible in the distance, enhancing the tranquil setting.
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.

Top Guest favourite
A bright kitchen area features modern appliances, including a retro-style refrigerator. A wooden dining table is set for a meal, surrounded by white chairs. Natural light enters through multiple windows, complementing the warm, rustic tones of the stone flooring and beams.
Apartment in Monsampietro Morico
5 out of 5 average rating, 41 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.

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, 83 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.

Guest favourite
The spacious living area features a high wooden ceiling, enhancing openness and light. A comfortable blue sofa sits prominently, accompanied by a wooden dining table. A flat-screen TV is positioned across from the seating area, while large windows offer views of the surrounding nature.
Holiday home in Pineto
4.97 out of 5 average rating, 32 reviews

Relais L'Uliveto – Dimora Stefania

Welcome to Relais L'Uliveto, our spacious and welcoming home built in 2023 using the best energy-saving technologies. The accommodation is finely furnished, surrounded by nature, just 5 minutes from the sandy beaches of Pineto and the charming medieval village of Atri. With its 90 square meters, it is ideal for families, groups of friends or couples who wish to live an authentic and unique experience. The property enjoys breathtaking views of the sea and mountains.

Guest favourite
An expansive pool is surrounded by a smooth stone deck, featuring a bright pink inflatable float. Lush greenery and a view of rolling hills stretch beyond the water, under a clear blue sky, creating a serene outdoor space for relaxation.
Home in Mosciano Sant'Angelo
5 out of 5 average rating, 15 reviews

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! 🌟

Superhost
Cottage in Campofilone
5 out of 5 average rating, 4 reviews

Mondomini Panoramic cottage with stunning view

Rilassati e ricaricati in quest'oasi di quiete ed eleganza, con un incredibile panorama su mare, colline marchigiane, montagne, immerso in un grande oliveto. Il cottage è accessibile e dotato di 2 camere da letto: una matrimoniale, una con divano letto con materasso da 16 cm estremamente confortevole come letto matrimoniale; due bagni, soggiorno e cucina attrezzata. Arredato con gusto e mobili di antiquariato. Perfetto per lunghi periodi di smart working.

Top Guest favourite
Holiday home in Grottammare
4.96 out of 5 average rating, 79 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.

Superhost
Villa in Colli del Tronto
4.85 out of 5 average rating, 92 reviews

Frescoes and Centuries-Old Park– Villa Mastrangelo

A well-known residence in our area: You can easily find us online as a local tourist landmark. Self check-in at any time Discounts for longer stays (contact me) 🏰 Exclusive apartment of over 150 m² 🌿 Private 200 m² garden with century-old plants – PET FRIENDLY 🚗 Private parking (open and closed) FREE 📶 FAST Wi-Fi and Smart TV ☕ Kitchen: coffee, tea, oil, vinegar, sugar, salt, etc. 🧺 Bed linen, towels, soap

Guest favourite
Condo in Grottammare
5 out of 5 average rating, 9 reviews

Boutique Apt • Umbrella Included • 300m Beach

Alba Unda • Retreat Concept is an elegant boutique apartment in Grottammare, just a 5-minute walk from the sea, with a beach umbrella and 2 sunbeds included during the summer season. Spacious and bright (~130 sqm), it features 2 bedrooms, a stylish living area, a fully equipped kitchen, and 2 bathrooms (shower and whirlpool tub). Air conditioning in all rooms and free parking available just outside.

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.
Apartment in Civitanova Marche
4.94 out of 5 average rating, 17 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