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Family-friendly vacation rentals in Estreito da Calheta

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Quick stats about vacation rentals that are family-friendly in Estreito da Calheta

  • Total vacation rentals

    Explore 210 vacation rentals in Estreito da Calheta

  • Nightly prices starting at

    Estreito da Calheta vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 6,690 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Estreito da Calheta vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Estreito da Calheta rentals

  • 4.8 Average rating

    Estreito da Calheta stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Estreito da Calheta

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

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Guest favorite
A spacious bed is centered in the room, adorned with decorative pillows and a colorful blanket. Nightstands are positioned on either side, each featuring soft lighting. A decorative straw hat and a bright flower are placed on the bed, enhancing the serene atmosphere.
Villa in Estreito da Calheta

Casa Rural @ Casas Da Vereda

Relax in class at 250 meters high on the sunny South West coast of Madeira, enjoying sunset and ocean views from the heated pool! The Casas Da Vereda are ideally located in a quiet countryside area with nothing but nature between you and the ocean. At 30 minutes drive from Funchal, 5 minutes drive to rock beaches in seaside villages / sand beaches by the marina of Calheta / “levada” walks. Please note that one can rent any combination of Casa Palheiro (T0), Casa Rural (T1), and (Casa Eco T2)!

4.95 out of 5 average rating, 170 reviews
Superhost
A glimpse of the exterior of the unique dome tents is provided, surrounded by lush greenery and tropical plants. A wooden walkway leads through the garden area, offering access to the tents while showcasing the natural landscape nestled among the hills.
Tent in Achadas da Cruz

Be adventurous , something completely different

Located in the north-western part of the island ,its an amazing location protected by conservation laws that have kept the area free of over development. With epic mountain and sea-views (the photos don't do it justice) the tents are located 450m above the coastline. If a place to relax and unwind is what you after then this would be the place to come to. There are also some amazing levada walks to explore in the area.There are three tents on the property so you might have neighbours.

4.87 out of 5 average rating, 788 reviews
Guest favorite
An outdoor dining area features a wooden table set with dishes and plants, surrounded by a few chairs. The rustic orange exterior of the adjacent building complements the lush greenery. The sea view can be seen in the background under an overcast sky.
Home in Arco da Calheta

Mango House

House with superb sun exposure, peaceful and stunning views over the sea and the mountain. Has 2 bedrooms (one with a double bed and the other with two single beds easily convertible into a double bed), a complete bathroom. On the ground floor open space with kitchen / living and dining room and toilet. Furniture and careful decoration. Outside enjoy the garden and the pleasant dining space with incredible views of the sea. The barbecue, mini-pool and shower complete your well-being.

4.93 out of 5 average rating, 119 reviews
Guest favorite
A yurt is positioned amidst vibrant yellow flowers, set against a backdrop of lush greenery. The coastline and a winding road are visible in the distance, with the ocean meeting a partly cloudy sky, creating a serene and natural landscape.
Yurt in Ponta do Sol

Mango Yurt ~Eco-Glamping in a Hidden Paradise

Wake up in total privacy, surrounded by a lush permaculture garden where you can see, taste, and smell nature’s abundance. At Canto das Fontes, in the sunny Sítio dos Anjos, it feels like eternal spring all year — even when other parts of Madeira are cooler. An award-winning regenerative eco-glamping where sustainability meets comfort and luxury, with a natural pool, Honesty Ba,r and stunning views of the sea and waterfall. 💧🌿 More pictures and vibes: @cantodasfontes

4.97 out of 5 average rating, 473 reviews
Guest favorite
An outdoor dining area is set up under a wooden gazebo, featuring a large table surrounded by metal chairs. A picturesque view of the ocean and cliffs is visible in the background, illuminated by the warm glow of sunset. The space includes decorative lights strung overhead.
Villa in Seixal

Madeira Black Sand House by Stay Madeira Island

Stay Madeira Island presents Madeira Black Sand Beach House! Set on the north coast of Seixal beach, Madeira Black Sand Beach House offers a dream view towards the black sand and the deep blue sea surrounded by green cliffs. This century old stone house has been with the same family for 30 years and was used as a weekend second home. The owners decided to share this unique spot with the world and the refurbished plan had the guest's comfort in mind.

4.93 out of 5 average rating, 192 reviews
Top guest favorite
A modern house with a vibrant red roof is positioned on a hillside, overlooking the ocean and surrounding landscape. The outdoor area includes a swimming pool and a spacious terrace, offering expansive views of both the coastline and lush greenery.
Villa in Arco da Calheta

CASA SOL E VISTA 2

Casa Sol e Vista 2 is located in one of the best locations in the parish, next to house no. 1. It has 2 bedrooms, a living room/kitchen and 3 bathrooms, accommodating 6 people. The house is located on top of a hill, which gives the house an extraordinary view. Outside, there is a barbecue, a large garden and a swimming pool. Absolute tranquility. Come spend a few pleasant days at Casa Sol e Vista 2. Contact Duarte Paulo

4.98 out of 5 average rating, 106 reviews
Top guest favorite
A small round table is set on a terrace, featuring two glasses of orange juice, a plate with various fruits, and croissants. In the background, lounge chairs are visible, complemented by expansive ocean views under a clear blue sky.
Apartment in Arco da Calheta

Martinho Apartment View

Modern apartment with an extraordinary view over the Atlantic Ocean and over the coast of Calheta. Our apartment consists of 1 bedroom with a double bed, living room, 1 bathroom and kitchen equipped with all that´s necessary for your vacation, we include Wi-Fi and private parking. Outside there are sun loungers for sunbathing and a large balcony to relax and enjoy the wonderful sea view. Your dream vacation is here!

4.99 out of 5 average rating, 153 reviews
Top guest favorite
An infinity pool stretches over a wooden deck, with views of the expansive Atlantic Ocean and dramatic cliffs. Sunlight reflects off the water's surface, enhancing the serene atmosphere. Surrounding greenery complements the natural setting, inviting relaxation and contemplation.
Apartment in Paul do Mar

Meu Pé de Cacau - Studio Papaia in Paúl do Mar

Meu Pé de Cacau is a tropical fruit garden surrounded by dramatic cliffs to the north-east and the vast Atlantic Ocean to the south-west. Four beautifully designed and sustainably built studios share the property with an infinity pool, social areas and luxurious plantations hosting hundreds of different tropical fruits, planted on traditional agricultural terraces hand crafted in basalt stone.

4.99 out of 5 average rating, 225 reviews
Top guest favorite
The image captures a view of Casa Nambebe, with a terracotta roof and surrounded by lush banana trees. An inviting infinity pool reflects the blue ocean, while the rugged coastline and greenery enhance the tranquil setting. The house is positioned on a hillside overlooking the sea.
Home in Ponta do Sol

Typical house above the sea

"Casa Nambebe" is a typical Madeiran house. Situated on the south slope of Madeira island, it is a great place to relax and enjoy a beautiful view of the sea. The house is placed in the middle of a land of banana trees where the contact with nature is immediate and the infinite pool will have you feel like you're in the ocean. Every sunset is unique. Número de licença ou registo 38381/AL

4.99 out of 5 average rating, 201 reviews
Top guest favorite
An infinity pool stretches across the scene, seamlessly merging with the horizon of the ocean. Surrounding greenery adds a touch of nature. Sun loungers are positioned on a terrace, offering a peaceful space for relaxation, with stunning views visible in all directions.
Home in Arco da Calheta

Villa Pérola | Pool & Panoramic Ocean View

Experience Madeira at Villa Pérola, an elegant villa in Arco da Calheta with a private pool and panoramic Atlantic views. With 3 bedrooms, modern interiors and spacious outdoor areas, it’s the perfect place to relax, enjoy spectacular sunsets and spend an unforgettable holiday by the sea.

4.95 out of 5 average rating, 44 reviews
Top guest favorite
The image features a bright yellow house surrounded by palm trees and blooming foliage. A staircase leads to the entrance, which is illuminated by natural light. The upper balcony can be seen with decorative railing, enhancing the overall welcoming appearance of the property.
Home in Jardim do Mar

Sofia's Place

In Sofia's Place (House of Sofia) breathes the spirit and the culture in a cosmopolitan and sophisticated accommodation in the heart of one of the most exclusive and romantic dream in the world. The contrast provides intense experiences. ATTENTION to : outras informações

4.95 out of 5 average rating, 159 reviews
Top guest favorite
A sunny space features a splash pool surrounded by well-maintained grass and tropical plants. White walls contrast with dark volcanic rock in the background. A covered outdoor dining area is visible, providing a shaded space for meals while enjoying the outdoors.
Cottage in Arco da Calheta

Villa Papaya

An Outstanding Location, with a Fabulous View. Splash Pool and a Table to do meals outside. Unforgetable Sunset, with the sea and the Marina View! Villa Papaya Address: Rua Serra D’Água - Vereda do Morgadinho N. º 24 9370-076 Arco da Calheta

4.98 out of 5 average rating, 219 reviews

Popular amenities for Estreito da Calheta family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
A charming exterior view of the Cottage Pearl showcases a stone facade with blue window shutters. The landscaped garden features comfortable lounge chairs, a gazebo with draped fabric, and vibrant flowers, all framed by surrounding hills. Soft outdoor lighting enhances the inviting atmosphere.
Cottage in Paul do Mar

Cottage Pearl-Rural Holiday Experience by SeaPearl

4.94 out of 5 average rating, 137 reviews
Guest favorite
A private balcony features a hanging chair and two woven chairs around a small table. A panoramic ocean view is visible, showcasing the tranquil blue water and a well-maintained pool below. Lush greenery is present, enhancing the outdoor space.
Apartment in Arco da Calheta

Madeira Island

4.9 out of 5 average rating, 161 reviews
Superhost
A charming outdoor space features a wooden pergola draped with sheer curtains, providing shade over a hot tub. Nearby, a seating area with dark wicker furniture is set against a backdrop of vibrant greenery and blooming flowers, along with a few white lounge chairs.
Apartment in Lombo Do Doutor

Beautiful Views - Apartment Fontes

4.87 out of 5 average rating, 248 reviews
Superhost
A modern geodesic dome stands on a wooden deck, featuring expansive transparent panels that provide panoramic views of the surrounding landscape. A private jacuzzi is visible in the foreground, accompanied by yellow lounge chairs and a small dining set, enhancing the outdoor relaxation space.
Dome in Prazeres

Soul Glamping| jacuzzi| faraway| reconnect| luxury

4.9 out of 5 average rating, 111 reviews
Guest favorite
A spacious infinity pool overlooks the coastline and ocean, surrounded by sun loungers and palm trees. The house features large glass doors that provide stunning views of the surrounding landscape. The tranquil setting highlights the connection between the property and its natural surroundings.
Home in Ponta do Sol

Relax Over The Sea -12391/AL

4.98 out of 5 average rating, 103 reviews
Guest favorite
A dining table is set for four, overlooking a serene ocean view. Glassware and dinnerware are arranged neatly, while a jacuzzi is visible in the foreground. The sunset creates a warm ambiance, enhancing the overall tranquil setting.
Hut in Tabua

Glamping Maracujá: Oasis Paradise

4.99 out of 5 average rating, 157 reviews
Guest favorite
Villa in Fajã da Ovelha

Ocean views: 3-bed villa with terraces & Hot-Tub

4.93 out of 5 average rating, 109 reviews
Superhost
A scenic view of rolling hills covered with banana trees and a distant mountain landscape can be seen. The coastline features calm waters, while a green lawn with a wooden pergola is visible in the foreground. A clear sky enhances the tranquil atmosphere.
Cottage in Ponta do Sol

Tropical Lovers - Levada & Bananas cliff

4.89 out of 5 average rating, 207 reviews

Family- and pet-friendly home rentals

Guest favorite
A cozy room features wooden walls and flooring, creating a natural ambiance. A spacious bed is dressed in light linens, complemented by a decorative throw. A small window allows natural light to enter, while a dark blue armchair adds a seating option in the corner.
Tiny home in Seixal

Seixal nature house 1

4.89 out of 5 average rating, 181 reviews
Top guest favorite
A wooden terrace features two lounge chairs facing the ocean, accompanied by a small table. The sea glistens under the sunlight, with blue skies and scattered clouds serving as a backdrop. Green foliage surrounds the area, enhancing the serene ambiance.
Cabin in Ponta do Sol

Casa Jean - Wooden house with sea view

4.94 out of 5 average rating, 297 reviews
Top guest favorite
A spacious terrace features a smooth wooden surface and a white railing, providing unobstructed views of the coastline and ocean. Sunlight bathes the area, highlighting the natural landscape of hills and the sea in the background.
Villa

House with stunning views surrounded by nature

5.0 out of 5 average rating, 117 reviews
Superhost
Cave in Arco da Calheta

Sunny Studio Beach Side III

4.77 out of 5 average rating, 116 reviews
Top guest favorite
Home in Boaventura

Casa "Just Nature" , Madeira Island

4.89 out of 5 average rating, 350 reviews
Guest favorite
A private infinity pool is set against a backdrop of the ocean, surrounded by lush tropical plants. Comfortable seating, featuring blue cushions, faces the pool and ocean views, creating a relaxing outdoor space. The bright sky enhances the tranquil atmosphere.
Home in Funchal

Seafront Home in Old Town Funchal w Pool & Garden

4.94 out of 5 average rating, 117 reviews
Top guest favorite
An outdoor seating area is highlighted by a decorative pillow featuring a floral design, resting against a woven chair. In the background, the infinity pool overlooks the expansive blue Atlantic ocean, framed by a clear sky.
Home in Tabua

Old Wine Villa

4.95 out of 5 average rating, 150 reviews
Guest favorite
A serene swimming pool reflects the sunset sky, surrounded by sun loungers and a hammock. The villa's exterior features large sliding doors, allowing for open access to the outdoor space, while a distant palm tree adds a touch of tropical ambiance.
Villa in Fajã da Ovelha

Casa Amarela (Stylish and Traditional Villa)

4.81 out of 5 average rating, 243 reviews

Family-friendly home rentals with a pool

Guest favorite
Villa in Arco da Calheta

Casa Diana Pool and Sea views

4.89 out of 5 average rating, 182 reviews
Guest favorite
A large heated saltwater pool is set against a backdrop of ocean and mountain views, framed by modern glass doors. Sunlight reflects off the water, enhancing the tranquil atmosphere. Spacious terraces surrounding the pool provide ample space for relaxation.
Villa in Arco da Calheta

Villa Lara, sea views, heated Pool A/C

4.94 out of 5 average rating, 117 reviews
Top guest favorite
Home in Arco da Calheta

Eco Fajã Villas - Deluxe - 60m above sea level

5.0 out of 5 average rating, 6 reviews
Top guest favorite
A spacious outdoor area features a modern swimming pool with clear blue water. Surrounding the pool are several lounge chairs arranged neatly, offering stunning views of the ocean and nearby village. The landscape includes lush greenery and distant rooftops, providing a serene backdrop.
Cottage in Estreito da Calheta

Casa dos Reis

5.0 out of 5 average rating, 30 reviews
Superhost
Villa in Estreito da Calheta

Grey Rock Villa 1 bedroom

5.0 out of 5 average rating, 4 reviews
Top guest favorite
A modern bedroom is presented with large glass doors that offer expansive sea and mountain views. A spacious bed is dressed with white linens, complemented by a decorative throw and a rolled towel. A pink accent chair adds a pop of color to the neutral decor.
Villa in Estreito da Calheta

King´s View (Heated Pool and Sea View)

4.93 out of 5 average rating, 55 reviews
Top guest favorite
A private deck offers an expansive view of the ocean, surrounded by lush greenery. A dining table and chairs are positioned under a shaded pavilion, providing a perfect spot for relaxation. The area combines natural beauty with a tranquil atmosphere.
Cottage in Fajã da Ovelha

Casa Mar - Quinta Falcões do Sol

5.0 out of 5 average rating, 54 reviews
Top guest favorite
A modern villa is set against a mountainous backdrop during twilight. The property features large glass doors opening to a terrace with dining furniture. A serene pool reflects the evening sky, surrounded by lounge chairs and landscaped gardens.
Villa in Paul do Mar

Quinta Marefe - On the stunning west coast

5.0 out of 5 average rating, 39 reviews

Destinations to explore