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Family-friendly holiday rentals in Monte San Martino

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Top-rated family-friendly rentals in Monte San Martino

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

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Villa in Castelraimondo

Villa Ermelinda · Ville Carborello Weddings

Villa Ermelinda is a private 16th-century villa set among the rolling hills of Le Marche, ideal for intimate weddings, destination weddings and exclusive stays. It offers exclusive use, a panoramic pool, gardens, a big terrace and beautiful spaces for symbolic ceremonies, poolside aperitifs and dinners under the stars. Hosting up to 18 guests, it also works perfectly with nearby Villa Nasca & Villa Adele, just a few minutes away, for larger wedding groups and unforgettable wedding weekends.

4.82 out of 5 average rating, 11 reviews
Guest favourite
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.
Home in San Vittoria in Matenano

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.

4.84 out of 5 average rating, 43 reviews
Guest favourite
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.
Home in Penna San Giovanni

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.

5.0 out of 5 average rating, 8 reviews
Top Guest favourite
The image captures a serene sunset over a private pool, with lush green grass surrounding the area. Sunlight casts a warm glow on the villa's exterior, highlighting large windows that reflect the fading daylight. Trees and hills are visible in the background, enhancing the peaceful setting.
Villa in Servigliano

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.

4.97 out of 5 average rating, 34 reviews
Guest favourite
Vibrant sunflowers bloom in the foreground, creating a lively scene against the rolling hills of Le Marche. A rustic stone building is positioned amidst lush greenery, while the expansive landscape showcases fields and distant towns under a clear blue sky.
Apartment in Mogliano

Experience Authentic Italian Village Life

Located in the heart of Le Marche, ranked 2nd in Lonely Planet’s 2020 list of “Top 20 Regions in the World to Visit.” This spacious apartment and garden offer the perfect base to relax or explore. Within 40 mins’ drive of mountains, lakes, and the sea, with many ancient hilltop towns nearby. Just 5 mins from Mogliano, where you’ll find everything you need for your stay. Nature reserves, outdoor markets, health spas, hiking, biking, and riding trails are all within easy reach.

4.98 out of 5 average rating, 45 reviews
Top Guest favourite
An infinity pool is set against a panoramic landscape, showcasing rolling hills and a clear blue sky. Comfortable lounge chairs are positioned nearby on a wooden deck, inviting relaxation while enjoying the serene views.
Apartment in Montalto delle Marche

House with pool, 1st floor, Villa Cerqueto

Located on the 2nd floor and ideal for 6/7 people. Equipped with all the comforts to enjoy 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.

5.0 out of 5 average rating, 73 reviews
Guest favourite
Condo in Monte San Martino

Room in nature with lake view - 3

Separate apartments overlooking Lake San Ruffino and a beautiful view of the Sibillini Mountains. The view of the lake is accompanied by the sound of the animals that inhabit it and the surrounding nature. The place is an oasis of peace: it's suitable for those who love nature and want tranquility. There are several species of birds and it's the ideal place for those who love to photograph. The accommodation does not have a kitchen but there is a small refrigerator.

5.0 out of 5 average rating, 8 reviews
Guest favourite
An indoor wellness area features a heated hydromassage minipool for six, surrounded by wide glass panels that provide views of the lush outdoor landscape and an inviting blue swimming pool beyond. Natural wood beams enhance the room's warm aesthetic.
Apartment in Gualdo

Elisei Farmhouse – Attic, Pool, 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

5.0 out of 5 average rating, 7 reviews
Top Guest favourite
A charming, two-story farmhouse features terracotta walls and a sloped roof, surrounded by lush greenery. Potted plants frame the entrance, with a wooden table and chairs positioned outside under a shaded umbrella, offering inviting outdoor seating and scenic countryside views.
Villa in Sant'Angelo in Pontano

Traditional 3-bedroom cottage with large garden

Forget your worries in this spacious and serene space. Absolutely tranquil, but less than a five minute drive from the bustling village of Sant’Angelo, which has three restaurants, three bars, and a theatre, as well as all local services. Relax and enjoy the views in the garden, or drive half an hour to the beach or a lake in the mountains, or explore the many beautiful hilltop towns in the area. Something for all tastes!

4.98 out of 5 average rating, 42 reviews
Guest favourite
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.
Home in Serra

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.

4.94 out of 5 average rating, 35 reviews
Top Guest favourite
The aerial view showcases the elegant Guest House surrounded by well-manicured green landscapes, vineyards, and trees. A winding gravel driveway leads to the house, highlighting its rustic charm and tranquil setting amidst the rolling hills of the Marche region.
Farm stay in Cingoli

The Guest House of the Tavignano Estate

The Tavignano estate is located in the heart of the Marche region, within the famous DOC of Verdicchio dei Castelli di Jesi, between the valleys of the river Esino and the Musone on one side, and between the Apennines and the sea on the other side. From the highest promontory of the Estate dominates the manor house, which houses the barrique, the family house, and an elegant Guest House.

4.98 out of 5 average rating, 88 reviews
Top Guest favourite
Villa in Sant'Angelo in Pontano

Villa in the Sibillini Mountains, Pool & Privacy

Private pool villa in Sant’Angelo in Pontano, among the rolling hills of Marche at the foot of the Sibillini Mountains. Sleeps up to 8 with 4 double bedrooms, all with en-suite bathrooms (3 upstairs + 1 in a separate annex), Wi-Fi and air conditioning. Large shaded porch for outdoor dining, lounge corners, and an outdoor BBQ/oven area. Great base for the Sibillini Park and Lake Fiastra.

5.0 out of 5 average rating, 5 reviews

Popular amenities for Monte San Martino family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

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

Hideaway Cottage, amazing country views, hot tub

4.88 out of 5 average rating, 116 reviews
Top Guest favourite
A charming stone cottage is shown, featuring a sloped roof and large glass windows that provide panoramic views. Soft lighting accentuates the exterior, while the surrounding grassy area leads the eye to the distant hills.
Cabin in Cerreto d'Esi

Hillside chalet in stone and wood.

4.99 out of 5 average rating, 163 reviews
Superhost
The image captures a modern living space with large openings framing a stunning sunset view. The horizon is painted in shades of pink and purple, while a serene infinity pool glimmers in the foreground. Cozy bathrobes are hung nearby, enhancing the relaxation setting.
Villa in Coste

SUNSET SUITE SPA

4.92 out of 5 average rating, 112 reviews
Guest favourite
A sleek bathroom is equipped with a glass-enclosed shower featuring ambient lighting and modern fixtures. Adjacent to it, a wooden sauna offers a warm and inviting retreat. The room features wooden flooring, enhancing the overall cozy ambiance.
Holiday home in Amandola

House - Il Gioiello - with Jacuzzi and Sauna

4.95 out of 5 average rating, 43 reviews
Guest favourite
A modern building complex is set against rolling hills, showcasing a vibrant landscape of agricultural fields and distant mountains under an overcast sky. Olive trees and flowering shrubs are visible in the foreground, adding greenery to the serene rural setting.
Apartment in San Ginesio

Deluxe apartment

5.0 out of 5 average rating, 9 reviews
Guest favourite
A rustic farmhouse is set against a backdrop of rolling hills and clear skies. The stone structure features a tiled roof and wooden shutters. In the foreground, colorful flowers dot the lush green grass, enhancing the serene landscape.
Farm stay in Montemonaco

La Cascina apartment, Sibillini National Park

4.95 out of 5 average rating, 22 reviews
Guest favourite
A living area showcases a brown sofa and a green armchair, positioned near a small wooden table and a television. Exposed wooden beams highlight the ceiling, while a wooden staircase leads to the upper level. Stone walls add a rustic touch to the space.
Cabin in Meriggio

Chalet Fiastra

5.0 out of 5 average rating, 16 reviews
Top Guest favourite
An outdoor terrace is equipped with a yellow tablecloth-covered table set for breakfast. Plates of pastries and a pitcher of orange juice adorn the table, while surrounding views include lush greenery and architectural details in bright sunlight.
Home in Ascoli Piceno

home holidays - b&b

4.88 out of 5 average rating, 96 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A snow-covered entrance is framed by a brick fence and gate, leading to a single-story chalet. The pathway is lined with greenery and a unique tree, while falling snow enhances the peaceful ambiance of the setting.
Cabin in Montefortino

Villa Sibilla

4.99 out of 5 average rating, 82 reviews
Top Guest favourite
A spacious sleeping area features rustic stone walls and exposed wooden beams. Natural light floods the room through large, sheer purple curtains, illuminating a double bed with a floral bedspread and a nightstand beside it. A wooden door leads to an outdoor area.
Farm stay in Montalto delle Marche

Inzolia Apartment

5.0 out of 5 average rating, 10 reviews
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

Casale Biancopecora, Casa Cerqua

5.0 out of 5 average rating, 45 reviews
Top Guest favourite
Villa in Colli del Tronto

Frescoes and Centuries-Old Park– Villa Mastrangelo

5.0 out of 5 average rating, 15 reviews
Top Guest favourite
A wooden pool is set within a landscaped area, featuring clear water and steps for entry. Relaxing lounge chairs are positioned nearby on the sun-drenched outdoor space, with greenery framing the scene. An umbrella offers shade, enhancing the tranquil outdoor environment.
Home in Cingoli

Farmhouse with garden and pool for exclusive use of wifi

5.0 out of 5 average rating, 54 reviews
Guest favourite
The entrance of the apartment features a wooden door framed by potted flowers, enhancing the inviting atmosphere. A stone path leads to the entry, bordered by greenery and vibrant blooms, while the rustic architecture is complemented by a sloping roof and window planters.
Home in Amandola

House with a Garden

4.83 out of 5 average rating, 18 reviews
Superhost
An outdoor dining area is set beneath a large umbrella, featuring a wooden table topped with blue plates and glasses. A variety of fruits and a basket are arranged alongside bottles of wine. The pool glimmers in the background, surrounded by sun loungers and greenery.
Villa in Massa Fermana

Villa Malu- Private villa, pool, Le Marche

4.68 out of 5 average rating, 19 reviews
Guest favourite
An aerial view captures a villa surrounded by the natural landscape of the Sibillini Mountains. The structure is nestled among trees, with the peaks of the mountains visible in the background against a clear blue sky.
Villa in Montefortino

[Sibillini view] Villa Amici

4.89 out of 5 average rating, 38 reviews

Family-friendly home rentals with a pool

Guest favourite
A tranquil salt-water pool is surrounded by lush gardens filled with blooming flowers. Lounge chairs are positioned along the poolside, offering views of rolling hills under a clear blue sky, enhancing the serene atmosphere of the outdoor space.
Home in Falerone

Farm house with exclusive access to the pool

4.89 out of 5 average rating, 18 reviews
Superhost
The property showcases a panoramic view of the surrounding hills, featuring a luxurious swimming pool at the center, surrounded by sun loungers. Two separate suites are visible, framed by lush greenery and well-maintained gardens, providing a serene outdoor space for relaxation.
Cottage in Casagatti

Casa Janna Cottage | Pool + 2 Suites

5.0 out of 5 average rating, 4 reviews
Guest favourite
A serene pool area is featured, with crystal-clear water reflecting the surrounding greenery. The rustic stone buildings in the background are framed by lush trees, while comfortable seating arrangements invite relaxation under the sun.
Casa particular in Matelica

I light up with immense

4.9 out of 5 average rating, 30 reviews
Top Guest favourite
A serene outdoor area is shown, featuring a rectangular pool surrounded by lush green grass. Sun loungers and umbrellas are positioned alongside the pool, under a clear blue sky. Rolling hills and trees frame the background, creating a peaceful natural setting.
Apartment in Sant'Elpidio a Mare

La Ponderosa Couple

4.97 out of 5 average rating, 34 reviews
Superhost
An outdoor dining area is set under a rustic stone shelter with a wooden beam ceiling. A wooden table with matching chairs is arranged, accompanied by decorative plants. The backdrop features a lush green landscape, enhancing the inviting atmosphere of the space.
Condo in Spoleto

Casa del Melograno in Pianciano

4.7 out of 5 average rating, 10 reviews
Home in Monte San Martino

Scenic Stay in Le Marche

4.5 out of 5 average rating, 4 reviewsThe inviting pathway leads to a attractively designed country house, surrounded by lush greenery and ornamental trees.
Villa in Smerillo

Villa Viola – Your serene countryside escape

5.0 out of 5 average rating, 4 reviews
Guest favourite
A serene garden area is surrounded by lush greenery and colorful flowers. A stone pathway leads through the garden, with a cozy outdoor seating area partially shaded by a pergola. The hillside in the background is adorned with trees displaying autumn colors.
Home in Saletta

Casa Eola Semi detached two bedroom rural cottage.

4.91 out of 5 average rating, 11 reviews

Destinations to explore