Vacation rentals in Estreito da Calheta

NEW! Madeira's last hidden mountain paradise!

Welcome to On the Rocks, your off-grid retreat where serenity meets full seclusion. Surrounded by the soothing sounds of cascading waterfalls, unwind with panoramic views that stretch across the horizon. Nestled in the heart of the island (15 min to both coasts), with hiking trails at your doorstep, you’re perfectly positioned to explore or relax. Whether seeking adventure or sun-soaked relaxation, this peaceful sanctuary offers the perfect balance—a home base to discover or a haven to recharge.

Villa Rada, by Pausa Holiday Rentals

This stylish two-level villa features three bedrooms, each with its own private bathroom, plus an additional guest WC. The open-plan interior offers a bright, welcoming atmosphere with air conditioning and contemporary design. Outside, enjoy a private pool, barbecue area, comfortable sun loungers, and an outdoor dining area, all set against stunning sea and mountain views. Located in a peaceful area of the island, it’s the perfect place to relax and experience Madeira in comfort and style.

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.

Sweet Paradise

Um paraíso no coração da Zona Oeste da Madeira orientado a sul e com um pôr do sol fantástico. Zona residencial calma e com bons acessos. A 5min da praia, comércio e restaurantes e com uma ótima localização para explorar a ilha. Uma casa moderna com piscina de água salgada e aquecida (mediante pagamento), boas áreas, churrasqueira, zona de solário, jardim com ervas aromáticas, ginásio e estacionamento. Toda a casa é climatizada e com uma cozinha equipada para celebrar ótimos momentos.

Blue Sea Tower, Private Heated Pool. Ocean view

Maximum Occupancy 6 Adults. We do not accept Groups of students or single sex groups. This CHARMING Villa commands an enviable location with stunning views over the Ocean. Traditional character combines with contemporary facilities, to offer luxury spacious accommodation. From the sweeping marble staircase to the full length upper Balcony, the property exudes space to relax, breathe and to enjoy the serenity of this peaceful village. The Private Pool is Heated all year.

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

Modern villa with fantastic views|InfiniteAtlantic

Set in one of Madeira’s most sought-after locations that combine nature with sun, this luxury villa combines modern architecture with outdoor living at its finest. The spacious terrace features a built In barbecue, outdoor dining table, and comfortable seating area – perfect for al fresco meals while enjoying superb views. The infinity swimming pool (optionally heated) blends seamlessly with the ocean horizon, creating an unforgettable backdrop for your holiday.

Casa das Moirinhas

A dream come true. An old haystack carefully transformed into a haven by the ocean, with sweeping views over the Atlantic and the village of Paul do Mar. Located on a royal road, Casa das Moirinhas is designed for those seeking tranquility and contact with nature in a unique setting. Where the blue of the ocean meets the deep green of the mountains, creating a serene and inspiring environment, ideal for switching off, slowing down and relaxing.

The Sunset Avenue w/infinity pool(optional heated)

Sunset Avenue · The Residence é uma residência exclusiva à beira-mar, situada no Paul do Mar, um dos locais mais especiais da Madeira para viver o oceano e o pôr do sol. Oferece uma combinação rara de localização privilegiada, privacidade e conforto de alto nível, ideal para famílias ou grupos que procuram uma estadia memorável. Aqui, o mar está literalmente à sua frente — e cada final de dia transforma-se num espetáculo natural inesquecível.

Arbor Villa: Nature Retreat

Arbor Villa is a boutique 4-bedroom retreat in Campanário, Madeira, with sweeping sea views from every room. Nestled in the mountains, it offers a private pool, BBQ, and spa-inspired interiors where you can wake to birdsong and a gentle stream. Just minutes’ drive from Fajã dos Padres, Ponta do Sol, and Funchal, it’s ideal for exploring Madeira. A car is recommended. Perfect for guests who value nature, exploration, and relaxation.

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.

Socalco Nature Calheta - Hall House

No Socalco Nature Hotel, combinamos turismo rural, atelier gastronómico e farming numa única experiência. Aqui, os nossos hóspedes entram em contacto com a natureza e metem a “mão na massa”. As plantas, as flores, as árvores de frutos, os cursos de água, as grutas e as vistas deslumbrantes sobre o mar fazem da sua estadia no Socalco uma experiência inesquecível.