
Holiday rentals with a pool in Estreito da Calheta
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Estreito da Calheta
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

Casa Palheiro @ Casas Da Vereda [Thatched-Roof House]
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)!

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.

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

☀️ 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.

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

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.

Heated pool, hot & cold AC, BBQ, views & parking
Modern 3-bedroom villa in Arco da Calheta with stunning sea & mountain views. Features a private heated pool, BBQ area, fully equipped kitchen, fast Wi-Fi, and secure garage. Walk to a handful of restaurants, cafés & pharmacy. Just 10 mins to Calheta Beach, 30 mins to Funchal. Ideal for couples, families (cot & highchair provided), or groups. Close to top Levada walks. Comfortable, spacious, and perfect for exploring Madeira.

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.

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!

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

Marina View Apartment - Pool, Aircon & Ocean View
Welcome to Marina View Apartment! A fantastic 2 bedroom apartment set in a peaceful location of Calheta, the South Coast of the island where not only the sun shines almost every day but a fantastic location to explore the island. What truly makes this place special is the generous private outside space and infinity pool with spectacular views of the Atlantic ocean and Calheta Marina.
Popular amenities for Estreito da Calheta rentals with a pool
House rentals with a pool

Villa Serenity

Oak tree / Ocean view

Vincents Place | Ocean View | Swimming pool

House of Christ the King

Casa Velha D. Fernando (Old House D. Fernando)

Vila Bela

Casa Cro | Ocean View

Kombi Studio(private pool) by STAY Madeira Island
Condo rentals with a pool

Tropical Sunset D

Ocean View Madeira Apartment

Casa Mar Azul 3

Luxury Big Apartment/Ocean view/Free Parking

Family friendly apartment swimming pool ocean view

Monumental Apartment

Whitehouse408 Sw.Pool & Pvt. Parking

New dream luxury appartment in the Madeira Palace.
Other holiday rentals with a pool

Villa Lara, sea views, heated Pool A/C

Vila Ladeira dos Zimbreiros

Top View Calheta

Villa Acacia- Spectacular Ocean view & heated pool

Villas Calhau da Lapa 10

Casa Joaquim by Rent2u, Lda

Secluded Sunset Villa on Cliff & 180° Ocean Views

Villa Palheiros - A Magnificent Ocean View
Quick stats about holiday rentals with a pool in Estreito da Calheta

Total holiday rentals
Explore 130 holiday rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta holiday rentals start at $31 AUD per night before taxes and fees

Verified guest reviews
Over 3,830 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
130 of Estreito da Calheta holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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!
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