
Holiday rentals with a pool in Calheta
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Top-rated rentals with a pool in Calheta
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Villa Orlanda Charm
This new and elegant Villa is situated in Calheta in about 100 m above sealevel. Fantastic views over the atlantic ocean and the sandy beach of Calheta, the green countryside and the terrace. In a few minutes drive you reach one of the most beautiful hiking region of Madeira, supermarket, Marina, beach and some more Bars / Restaurants in Calheta. You find all the comfort you might need for a unforgetable holiday: WLAN, barbecue, dishwasher, dryer, washing machine, microwave, TV and Playstation 4

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)!

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 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, a social toilet, open space with kitchen / living and dining room, furniture and careful decoration. Outside enjoy the garden and the pleasant dining space with incredible views of the sea. The barbecue and mini-pool complete your well-being.

Meu Pé de Cacau - Mango Studio in Paúl do Mar
Meu Pé de Cacau is a tropical fruit garden and island retreat 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.

Mango Yurt ~Eco-Glamping in a Hidden Paradise
Wake up surrounded by tropical banana trees, listening to the waves by the beach and the spring water falling down the waterfall. This new Glamping site in Madeira Island is the perfect spot to relax, camping in comfort & luxury surrounded by nature. More pictures at @cantodasfontes (insta)

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 Calheta rentals with a pool
House rentals with a pool

Villa Serenity by Rentallido

Vincents Place | Ocean View | Swimming pool

Casa do Penique ORGANIC

House of Christ the King

Villa Rubydom

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

Villas Calhau da Lapa 10

Casa do Lado
Condo rentals with a pool

Ocean View Madeira Apartment

Madeira Palace Sea View

COSY STUDIO AT LIDO WITH POOL

Casa Mar Azul 3

Luxury Big Apartment/Ocean view/Free Parking

Family friendly apartment swimming pool ocean view

Whitehouse408 Sw.Pool & Pvt. Parking

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

House with sea view and heated saltwater pool

Quinta Marefe - On the stunning west coast

Vila Aguarelas with pool by Stay Madeira Island

Villa Lara, sea views, heated Pool A/C

Cottage Palha, hanging in a tropical garden

Roraima House - Private Pool & Garden

Morning Glory - Penthouse

Top View Calheta
Quick stats about holiday rentals with a pool in Calheta
Total rentals
140 properties
Nightly prices starting at
$190 NZD before taxes and fees
Total number of reviews
5.2K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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