Family-friendly holiday rentals in Estreito da Calheta

An outdoor space is shown, featuring an infinity swimming pool with a clear blue surface. Surrounding the pool are sunbeds, a grassy area, and views of lush green hills under a partly cloudy sky. The villa's glass doors provide access to interior living areas.

4.97 out of 5 average rating, 101 reviews

Villa Palheiros - A Magnificent Ocean View

Perfect home to enjoy the nature and beauty the island of Madeira has to offer. This villa has a stunning ocean view, situated in a very quiet rural area, where you can enjoy a magnificent climate in a swimming pool with endless views. This villa was built and designed to offer the best comfort to its guests. Perfect housing for families, where you can also find all the necessary amenities in a maximum of 5 minutes by car. The air conditioner is a extra service (contact the owner for more info.)

4.98 out of 5 average rating, 160 reviews

Two lounge chairs in vibrant yellow and orange are positioned on a lush green lawn, offering a view of the ocean. Surrounding plants and trees enhance the tranquil garden setting, which features a partially fenced area for added privacy.

Villa in Fajã da Ovelha

Quinta São Lourenço – Casa Lagar | Sunset & Pool

Tourist tax included > no extra fees at arrival Free cancellation up to 5 days before your stay The « Quinta São Lourenço » is a traditional Madeiran property of 3 000 m² from the 19th century, renovated into independent houses. The Quinta is an ideal holiday destination and is well known for its dominant position on the Atlantic Ocean, its beautiful flower garden and its shared outdoor swimming pool. Let yourself be surprised by the majestic sunsets and take a break with the roar of the Ocean.

A modern villa is showcased with clean architectural lines and large glass windows, surrounded by a manicured lawn featuring palm trees. An outdoor dining table and chairs are arranged on a patio adjacent to the heated infinity pool, overlooking scenic views of the landscape.

4.98 out of 5 average rating, 105 reviews

Panoramic View: Lux 3 bed w/ heated pool

Stunning modern villa with a private, heated infinity pool, 3 bedrooms and bathrooms, enjoying sea & mountain views. Located in one of the most sought-after areas with the best weather in the South West of Madeira island, the villa is unique in that it has a dedicated entertainment floor. Situated 5 mins away from Calheta Beach with its excellent restaurants on the marina & the same distance from Madalena do Mar beach. The house enjoys sun on the pool area from late morning until sunset.

4.88 out of 5 average rating, 745 reviews

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.

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.

4.93 out of 5 average rating, 115 reviews

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.

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.

4.98 out of 5 average rating, 203 reviews

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

4.97 out of 5 average rating, 680 reviews

A secluded orange tent is positioned against a stunning sunset over the ocean. Vibrant colors fill the sky, with clouds gently illuminated. Lush greenery surrounds the tent, providing a sense of intimacy with nature in a tranquil, elevated setting.

Yurt in Ponta do Sol

Papaia Yurt ~ EcoGlamping 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

4.92 out of 5 average rating, 182 reviews

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.

4.99 out of 5 average rating, 141 reviews

The exterior of a stone house features a garden with green grass, bordered by flower beds and fruit trees. The building showcases multiple windows with red accents, surrounded by a hillside landscape under a clear blue sky.

Home in Corujeira

Quinta da Tabua

We prepare this house with your comfort and rest. The place is quiet with a great view of the sea and the mountains. It has a garden with some fruit trees and a porch that allows you to relax and feel the breeze while you read a book. You can prepare meals at the barbecue or in the kitchen, relax and watch TV in the living room, enjoy the comfort of the bedrooms, equipped with high quality mattresses and take a very warm, rested shower.

4.99 out of 5 average rating, 213 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.

Flat 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, 159 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!