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Family-friendly holiday rentals in Tolentino

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Tolentino

  • Total holiday rentals

    Explore 40 holiday rentals in Tolentino

  • Nightly prices starting at

    Tolentino holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 440 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Tolentino holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Tolentino rentals

  • 4.8 Average rating

    Tolentino stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated family-friendly rentals in Tolentino

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
Farm stay in Rustico, Polverigi
4.91 out of 5 average rating, 66 reviews

House in nature - Green Forest

Country house that offers moments of tranquility in a serene atmosphere, we produce DOC wine and EVO Oil. The Marche region is full of wonders given by Mother Nature, the sea, the mountains, the valleys dotted with rivers, the gorges and the natural passes of the Apennines, or built by the wisdom of renowned artists. But the works created by the simple hand of the farmer certainly do not disfigure in the panorama that opens before your eyes. "...may your walk be light, traveler, and your heart light."

Top guest favourite
The Sferisterio theater is highlighted by its grand brick colonnade, illuminated against a dusk sky. The curved structure features multiple seating levels with historic elements and a vibrant atmosphere, showcasing an audience gathered in anticipation of the evening performance.
Flat in Mogliano
4.94 out of 5 average rating, 34 reviews

Opera & Nature Lovers Loft Suite 30 mins 2 Opera

Located in the heart of Le Marche—ranked 2nd in Lonely Planet's 2020 list of "The Top 20 Regions in the World to Visit"—this sunny apartment offers the perfect base to relax or explore. Just 30 minutes from the world-renowned open-air opera venue, the Sferisterio in Macerata, and within an hour to mountains, lakes, and the sea. Discover ancient hilltop towns, nature reserves, outdoor markets, health spas, and scenic hiking, biking, and riding trails. 5 mins’ drive to the village of Mogliano.

Guest favourite
The outdoor area features a wooden hot tub surrounded by a spacious deck. Comfortable seating is provided with modern lounge chairs and side tables, set against a backdrop of rolling hills and expansive countryside views under a bright blue sky.
Cottage in Loro Piceno
4.88 out of 5 average rating, 112 reviews

Hideaway Cottage, amazing country views, hot tub

A cosy renovated traditional stone cottage surround by countryside with breathtaking views & wood~fired hot tub. It is secluded and peaceful yet only a 5 min drive to the local village and amenities. In 35 minutes by car you can find yourself in the Sibillini national park or in the other direction the Adriatic coast. Numerous local restaurants within 20 mins drive serving fantastic food. If you enjoy walking or hiking, cycling, shopping or just relaxing this is a great place.

Top guest favourite
An outdoor terrace with a shaded dining area is presented, featuring a large white umbrella over a dark table and several light-colored chairs. Stone walls surround the space, creating a private atmosphere, with greenery visible in the background.
Holiday home in Assisi
4.99 out of 5 average rating, 121 reviews

House with terrace and garden in the historic center

Three-room apartment, located in the upper part of the historic center of Assisi, with terrace and garden, can accommodate up to six people. The apartment with two bedrooms, two bathrooms and a fully equipped kitchen is ideal for families and long stays. The garden and terrace with table, chairs and umbrella will allow you to spend pleasant moments outdoors in complete relaxation. Bus terminal for Assisi station 150m away. National Identification Code (CIN) IT054001C24H030483

Top guest favourite
The exterior of a rustic stone building is captured, showcasing a two-story structure with multiple shuttered windows. A small balcony is visible on the upper level. Lush green grass and a few decorative plants frame the entrance, while a vehicle is parked nearby.
Flat in Urbino
4.96 out of 5 average rating, 204 reviews

Apartment in an old farmhouse 4 km from Urbino

Charming 45 sqm apartment in a finely renovated old farmhouse. On the hills, a 5-minute drive from Urbino, the accommodation is equipped with a kitchen and living room, private bathroom with shower and double bed. Third bed on the mezzanine. Wi-Fi, TV, free on-site parking, mosquito nets, fan, library, informational material for discovering the area. Breakfast is offered for the first 2 days of the stay, after which it will be the customer's responsibility to provide it.

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, 85 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.

Superhost
Barn in Macerata
5 out of 5 average rating, 3 reviews

Country Barn Retreat | Nature & Digital Detox

Former 19th-century hay barn immersed in the rolling hills of Le Marche. True silence, no phone signal, fast Wi-Fi and nature all around. Only 10 minutes from Macerata — yet a world away! Casa Galli is a restored late-1800s hay barn, attached to our family home and surrounded by open countryside. This is not a polished countryside resort: it is real rural life — light, birdsong, changing seasons, animals, earth. If that resonates with you, you’ll feel at home here ♥️

Guest favourite
An exterior view of a rustic stone farmhouse is presented, surrounded by lush greenery. A pool is visible in the foreground, bordered by manicured lawns and flower beds. Multiple buildings are arranged harmoniously within the serene landscape, showcasing a peaceful retreat.
Flat in Gualdo
4.88 out of 5 average rating, 17 reviews

Agriturismo Elisei appartamento piscina sauna spa

Are you looking for a quiet, relaxing place, surrounded by nature and away from the hustle and bustle? Do you want to discover the charm of the Monti Sibillini National Park and its villages? Choose the Elisei Farmhouse, small and for a few people, allowing each of the guests to have plenty of outdoor space. The farmhouse has a large garden with swimming pool, as well as a wellness area with sauna and spa. CIN (National Identification Code): IT043021B5CETGSYCI

Superhost
Home in Belfiore
5 out of 5 average rating, 3 reviews

Casale del Menotre | Countryside Umbrian Retreat

Just minutes from Assisi, between Rasiglia, Spello, and the Menotre Waterfalls, the tourist rental welcomes you. After a day discovering Umbria, just relax in the hot tub, hammock, deckchairs and BBQ area immersed in nature and the silence of the Umbrian landscape. The house has Wi-Fi, Smart TV with access to personal Netflix, air conditioning and 3 bedrooms, one of which has a private bathroom. Non-entrepreneurial tourist rental without additional services.

Top guest favourite
A cozy bedroom features a spacious bed dressed in light blue bedding. A stone wall adds texture alongside warm wooden beams overhead. A minimalist closet and shelving unit are integrated into the design, while a comfortable armchair invites relaxation in the corner.
Home in Maiolati Spontini
4.97 out of 5 average rating, 118 reviews

Dimora nel Borgo - A Relaxing Home

The “Dimora nel Borgo” is a cozy home in the medieval historic center of Maiolati Spontini. It offers a relaxed and comfortable atmosphere, thanks to the recent and careful renovation, and the quiet and peaceful surrounding environment, inside a courtyard of yesteryear. A few meters from the house there are always free parking spaces available, there are no ZTL restrictions regarding the historic center. The house is complete with all amenities.

Guest favourite
A dining area features a wooden table surrounded by six chairs, illuminated by a chandelier. A stone fireplace is positioned at the corner, adding character. An artwork is displayed on the wall, and a wooden cabinet stands nearby, showcasing the rustic charm of the space.
Holiday home in Pergola
5 out of 5 average rating, 5 reviews

Apartment "Ginestra"

Immersed in the lush countryside of Marche's hinterland is the ancient village of Ca 'Palazzo. The apartment "Ginestra", totally independent, has maintained the typical rustic style without sacrificing comforts. Available to guests there are large green areas, private patio, private parking, barbecue stations and an 18x7 infinity pool overlooking the mountain massif of Catria and Acuto. Conveniently located to discover the rich territory.

Guest favourite
Flat in Massa Martana
5 out of 5 average rating, 8 reviews

Umbrian-style house surrounded by greenery near Todi

Welcome to Fiori nel Fienile, a refuge in Massa Martana where peace, nature and silence reign supreme. If you want to disconnect from your routine, this house is for you. We are here to make your stay as comfortable and relaxing as possible. A strategic starting point for visiting the wonders of the green heart of Italy and a cozy home to return to after a day as true explorers. For activities, services, guides, tips, contact us!

Popular amenities for Tolentino family-friendly rentals

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Avg. price$268 SGD$259 SGD$253 SGD$167 SGD$181 SGD$255 SGD$297 SGD$297 SGD$210 SGD$212 SGD$222 SGD$286 SGD
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