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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.

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Guest favorite
Place to stay in Jardim do Mar
4.95 out of 5 average rating, 272 reviews

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.

Guest favorite
Villa in Estreito Calheta
4.94 out of 5 average rating, 156 reviews

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)!

Guest favorite
Home in Arco da Calheta
4.98 out of 5 average rating, 191 reviews

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

Guest favorite
Home in Arco Da Calheta
4.92 out of 5 average rating, 106 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, 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.

Guest favorite
Cottage in Jardim do Mar
4.96 out of 5 average rating, 185 reviews

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.

Guest favorite
Home in Arco Da Calheta
4.99 out of 5 average rating, 136 reviews

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.

Top guest favorite
Apartment in Paul do Mar
4.99 out of 5 average rating, 199 reviews

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.

Top guest favorite
Apartment in Jardim do Mar
4.99 out of 5 average rating, 137 reviews

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).

Guest favorite
Villa in Ponta do Sol
4.97 out of 5 average rating, 146 reviews

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!

Guest favorite
Home in Ponta do Sol
4.99 out of 5 average rating, 176 reviews

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

Top guest favorite
Apartment in Calheta
4.95 out of 5 average rating, 114 reviews

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.

Guest favorite
Yurt in Ponta do Sol
4.97 out of 5 average rating, 409 reviews

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

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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