Family-friendly vacation rentals in Estreito da Calheta

Place to stay in Jardim do Mar

The image captures a wooden-roofed structure situated beside a calm sea, with expansive views of the coastline and towering rocky cliffs under a clear blue sky. The serene waters glisten in the sunlight, providing a striking contrast to the natural landscape.

4.95 out of 5 average rating, 275 reviews

Uni WATER Studio

Wake up to absolute mind blowing scenery in this mezzanine featuring floor to ceiling high windows facing the island's stunning coastline, often requiring a second look to truly appreciate the beauty that this magnificent island has to offer. The mezzanine accommodates two people, has an ensuite bathroom, a fully equipped kitchen and also has access to its own private garden. Needless to say, our infinity pool is also there for you to enjoy and relax. Free parking is available in Jardim do Mar.

4.99 out of 5 average rating, 250 reviews

A modern kitchen is presented, featuring sleek black countertops and white cabinetry. Stainless steel appliances, including a refrigerator and microwave, are visible. A bowl of fresh fruit is placed on the counter, and large glass doors lead to a balcony with scenic views.

Home in Calheta

Top View House

Top View House é uma casa nova (remodelada em novembro de 2017) com dois quartos de dormir, uma sala, uma cozinha, duas casas de banho e duas varandas. Situada num bairro calmo em plena natureza com vistas exuberantes. Próxima da Levada Nova e de percursos pedonais (Rabaçal, 25 fontes, Lagoas da Dona Beja e do Vento), também a 10 minutos (de carro) de uma praia de areia amarela, Museu de arte contemporânea da Madeira – Mudas, supermercado, restaurantes, padarias, urgências, farmácia.

4.83 out of 5 average rating, 743 reviews

A modern tent structure is nestled among lush greenery, showcasing a geometric design. Natural vegetation surrounds the tent, with wooden steps leading up to the entrance. The clear blue sky complements the inviting atmosphere of this serene outdoor retreat.

Tent in Achadas da Cruz

Be adventurous , something completely different 2

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 neighbours.

4.98 out of 5 average rating, 193 reviews

A bright exterior space is shown with a round pool surrounded by a wooden deck. Sun loungers in green and umbrellas provide shaded areas. Colorful gardens with tropical plants encircle the house, which features large glass doors leading into an indoor living area.

Home in Arco da Calheta

Casa Sol e Vista

Moradia com boa vista e bom sol durante todo o dia. A casa está localizada num dos melhores locais da freguesia. Dispoe de dois quartos de dormir, sala / cozinha e duas casas de banho, com lotaçao para 6 pessoas. A casa esta situada no cimo de uma colina o que faz com que a casa tenha uma vista extraordinaria. No exterior tem um churrasco, um grande jardim e a piscina. Absoluta tranquilidade. Venha passar umas férias agradaveis na CASA SOL E VISTA. Contactar Duarte Paulo

Apartment in Jardim do Mar

An outdoor area presents a heated saltwater pool framed by vibrant green grass and blooming shrubs. A single lounge chair is positioned beside the pool, with the expansive ocean visible in the background under a clear blue sky. Sunlight reflects off the water's surface.

4.99 out of 5 average rating, 134 reviews

☀️ Bright & Spacious w/ Pool & Oceanside View :D

Modern studio in the sunny and serene coastal village of Jardim do Mar, south west of Madeira Island. Studio D features an open plan design with kitchenette, lounging area, TV (with Netflix), a cozy queen size bed, a spacious bathroom with washing machine and a private balcony with ocean and pool view (24° to 26° Celsius). Guests have full access to the garden and heated saltwater pool. New Tourism Tax already included in the price, so we'll take care of that for you.

4.97 out of 5 average rating, 412 reviews

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 Bar and stunning views of the sea and waterfall. 💧🌿 More pictures and vibes: @cantodasfontes

4.96 out of 5 average rating, 190 reviews

A modern stone-walled pool area features a turquoise water surface with a gentle waterfall. Sun loungers are positioned neatly alongside the pool, surrounded by lush greenery and ornamental grasses, creating a serene outdoor environment.

Cottage in Jardim do Mar

Stonelovers® (Heated Pool Optional) - Unit3

Settled in a stunning organic green land, contemplating an amazing sea view, spectacular cliffs, surrounded by pieces of cropland, banana plantations and vineyards, we have found what today is WOODLOVERS. Combining this dream place with our engineering, sustainability, renewable energies and permaculture background, we were pioneers in the construction of the first contemporary 100% WoodHouse in Madeira Island respecting the nature and the natural environment.

Farm stay in Arco da Calheta

The spacious interior features large glass walls, allowing a panoramic view of the ocean. Two wicker chairs with cushions are positioned to enjoy the scenery. A wooden table is visible nearby, framed by lush greenery and a thatched ceiling, creating a relaxed atmosphere.

4.94 out of 5 average rating, 111 reviews

C Torre Bella Gardens

Welcome to Torre Bela Gardens – Your Perfect Holiday Escape! 🌴🌺 Nestled on a captivating historic estate, your cottage was once the country retreat of British Counts from the island’s earliest days. Surrounded by an exotic fruit farm, a beautifully restored manor house, tranquil gardens, and a charming chapel, there's so much to discover right here. Prepare to be enchanted by incredible viewpoints and a serene atmosphere that invites relaxation. 🌴🍹

Tiny homes in Arco da Calheta

A serene sunset view is framed by silhouettes of trees and a hanging bird feeder. A small table and chairs are visible in the foreground, casting gentle shadows as the sun dips below the horizon, reflecting warm hues across the ocean.

4.96 out of 5 average rating, 112 reviews

Magro's House

This is an AL (local accommodation) studio, with about 36m2, modern, integrated in a centenary stone house – designated Casa Mãe – with a magnificent view to the Atlantic Ocean. Guests can access a beautiful garden with grass and indigenous/endemic plants as well a small garden with tropical fruits. You will enjoy magnificent sunsets and hear the sounds of nature – birds, frogs and butterflies in some seasons of the year.

4.98 out of 5 average rating, 189 reviews

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 Papaya 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.

4.97 out of 5 average rating, 147 reviews

An infinity pool offers panoramic ocean views, bordered by a well-maintained garden featuring blooming flowers and lush greenery. Sun loungers are positioned nearby for relaxation, while a shaded terrace area can be seen in the background, enhancing the tranquil ambiance.

Villa in Ponta do Sol

Villa Miradouro da Baleia by PAUSA Holiday Rentals

This magnificent, modern, private villa Miradouro da Baleia (Whale Watchtower) has some of the best ocean and mountains views on the island, with a infinity pool and located in a premium spot surrounded by spectacular cliffs, cropland, banana plantations and vineyards, it was carefully & tastefully restored/built in 2018 offering a unique experience of a Portuguese summer style accommodation!

Cottage in Arco da Calheta

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.

4.97 out of 5 average rating, 186 reviews

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

Popular amenities for Estreito da Calheta family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Apartment in Lombo Do Doutor

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.

4.87 out of 5 average rating, 219 reviews

Beautiful Views - Apartment Fontes

4.93 out of 5 average rating, 163 reviews

A modern living area features a comfortable sofa and a sleek chair, positioned by large glass doors that open to a balcony. A round coffee table rests on a patterned area rug, with scenic views of the surrounding landscape visible through the windows.

Home in Ponta do Sol

180º view over the West

Apartment in São Martinho

A pool area features a circular swimming pool surrounded by lounge chairs, with a view of the ocean in the background. The bright blue water contrasts with the light-colored tiles. Palm trees add a tropical touch to the serene atmosphere.

4.86 out of 5 average rating, 175 reviews

Swimming pool, balcony and sea view. Renovated studio.

4.86 out of 5 average rating, 174 reviews

A balcony scene features a table set with two plates of breakfast alongside a scenic view of the ocean. Two chairs are positioned around the table, and the horizon is visible under a clear blue sky, reflecting the sunlight.

Condo in Caniço

Family friendly apartment swimming pool ocean view

Apartment in São Martinho

A silhouette of a person practicing yoga is framed against a vibrant sunset, casting colorful reflections on the infinity pool. The expansive view includes ocean waves and distant mountains, enhancing the serene atmosphere of the outdoor area.

4.94 out of 5 average rating, 214 reviews

Atlantic Ocean View Apartment INFINITE POOL

Vacation home in Fajã da Ovelha

A spacious outdoor area is presented with lush green grass and vibrant flowering plants. Sunbeds and umbrellas provide relaxation options, while scenic hills and trees create a tranquil backdrop under a clear blue sky.

4.84 out of 5 average rating, 161 reviews

Ocean views: Exclusive loft with terrace & Hot-Tub

4.92 out of 5 average rating, 178 reviews

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

Apartment in Ribeira Brava

A private jacuzzi is positioned outdoors, offering scenic views of the sea and surrounding greenery. Bright blue skies enhance the tranquil atmosphere, while the clean lines and modern design of the jacuzzi contribute to a serene outdoor retreat.

4.94 out of 5 average rating, 134 reviews

Renala I "With Jacuzzi" by PAUSA Holiday Rentals

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 113 reviews

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 homes in Seixal

Seixal nature house 1

Townhouse in Ponta do Sol

A panoramic view of a lush hillside is presented, showcasing a collection of colorful homes with terracotta roofs nestled among verdant banana trees. The sky features a mix of clouds and sunlight, enhancing the vibrant landscape of Ponta do Sol.

4.82 out of 5 average rating, 217 reviews

Organic Phenomena

Cottage in Casas Próximas

An outdoor dining area is visible with wooden tables and chairs positioned against a stone wall. The ocean stretches out in the background with gentle waves, and a coastal rock formation creates a picturesque horizon under a clear blue sky among swaying trees.

4.89 out of 5 average rating, 267 reviews

Casa da Praia

Home in Jardim do Mar / Calheta / Madeira

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.

4.95 out of 5 average rating, 146 reviews

Sofia's Place

4.9 out of 5 average rating, 154 reviews

Cottage in Madeira

Casa dos Anjos 9224/AL

4.93 out of 5 average rating, 115 reviews

A well-maintained garden is highlighted by two turquoise lounge chairs positioned on vibrant green grass, accompanied by a large umbrella for shade. The stone exterior of the house is visible in the background, creating a harmonious blend with the outdoor seating area.

Home in Arco da Calheta

BHF Residences Ying Yang

4.87 out of 5 average rating, 112 reviews

An expansive terrace with a tiled floor offers unobstructed views of the coastline and lush green mountains. Railings outline the space, enhancing the connection with the natural surroundings. The sky above is bright, with a few clouds adding depth to the landscape.

Home in Ponta Delgada

Little Escape Madeira

4.92 out of 5 average rating, 106 reviews

A spacious bedroom is illuminated by ceiling lights, featuring a large bed with a neutral-toned blanket. A low sofa sits at the foot of the bed, while a small side table holds candles. A staircase is visible, leading to another area, alongside a modern wardrobe.

Villa in Ponta do Sol

Cecia Studio by Stay Madeira lsland

Family-friendly home rentals with a pool

Guest suite in Ponta do Sol

A serene sunset is captured over the horizon, viewed from an infinity pool that blends into the ocean. A palm tree silhouette adds a natural element, while the warm colors of the sky reflect softly on the water's surface.

4.94 out of 5 average rating, 116 reviews

A View For You 2

Apartment in Arco da Calheta

A modern villa is pictured with a spacious outdoor area, featuring a clear blue swimming pool surrounded by lounge chairs. Umbrellas provide shaded seating, while a view of the ocean and sky reflects the tranquil setting.

4.99 out of 5 average rating, 70 reviews

Casa Mar Azul 2

4.99 out of 5 average rating, 139 reviews

A private veranda is featured, showcasing a table with two blue chairs and a portable barbecue nearby. The space is shaded by a modern lattice roof, offering a comfortable spot for outdoor dining. Green grass surrounds the area, creating an inviting atmosphere.

Cottage in Calheta

In peaceful Prazeres | Qta Inácia Sunflower Studio

5 out of 5 average rating, 14 reviews

The image captures a serene view from inside the house, showcasing a large infinity-edge swimming pool that merges with the Atlantic Ocean. Lush greenery lines the poolside, and expansive glass doors open to the outdoor area, allowing natural light to fill the space.

Home in Paul do Mar

Vila Ladeira dos Zimbreiros

4.97 out of 5 average rating, 32 reviews

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 Calheta

Luxury Villa Pérola

Villa in Estreito da Calheta

A shaded outdoor seating area features two comfortable chairs facing a panoramic view of the Atlantic Ocean. Lush green plants frame the scene, enhancing the serene environment. A small table is placed between the chairs, complementing the peaceful setting.

4.95 out of 5 average rating, 75 reviews

Beige Rock Villa

4.96 out of 5 average rating, 91 reviews

An infinity pool reflects the sunset, with the coastline visible in the background. The modern villa is framed by transparent railings and lush palm trees, exhibiting large glass doors that invite natural light and panoramic views into the interior.

Home in Arco da Calheta

Villa Panorama - Luxury Villa with Jacuzzi-Calheta