
Vacation 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.

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.

Country House @ Casas Da Vereda
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
Villa with a good view and good sunshine throughout the day. The house is located in one of the best places in the parish. It has two bedrooms, living room / kitchen and two bathrooms, with a capacity for 6 people. The house is situated at the top of a hill which makes the house have an extraordinary view. Outside there is a barbecue, a large garden and the swimming pool. Absolute tranquility. Come spend A pleasant vacation in the HOUSE SUN and VIEW. Contact Duarte Paulo

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.

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.

Villa Bisa Atlantic View ,heated pool
A 2 bedroom villa located in Arco da Calheta. the property has 2 modern style bedrooms, 2 and a half luxurious modern bathrooms,outdoor shower ,new modern kitchen, living room, etc... The property has just been renovated,modern decorated with high quality furniture which is extremely comfortable. The villa also includes cable ,Satellite TV and internet. The property on the outside has BBQ ,pool with a panoramic Seaview ,a nice eating area.

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.

Modern & New Studio w/ Pool & Oceanside View | G 🌟
Modern studio in the sunny and serene coastal village of Jardim do Mar, south west of Madeira Island. Studio G features an open plan design with kitchenette, lounging area with TV (with Netflix), a cozy king sized bed, a spacious bathroom and a private balcony with ocean and pool view. We provide free Wi-Fi and free parking (the property is a minute walk from the village's centre and the main free parking lot).

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)
Popular amenities for Calheta rentals with a pool
House rentals with a pool

Villa Serenity by Rentallido

House of Christ the King

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

Sales House

Vila Bela

Villas Calhau da Lapa 10

Casa da Arvore in the eucalyptus forest, no neighbors

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

Ocean View Madeira Apartment

COSY STUDIO AT LIDO WITH POOL

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 vacation rentals with a pool

Vincents Place | Ocean View | Swimming pool

Villa Lara, sea views, heated Pool A/C

Roraima House - Private Pool & Garden

Peak A Boo (Private Heated Pool & Private Parking)

Top View Calheta

Villa Acacia- Spectacular Ocean view & heated pool

Premium villa, panoramic sea-view | Calheta Pearl

Botanica Living | Acacia Apt
Quick stats about vacation rentals with a pool in Calheta
Total rentals
150 properties
Nightly prices starting at
R1,215 ZAR before taxes and fees
Total number of reviews
5.6K reviews
Family-friendly rentals
110 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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