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Vacation rentals with a pool in Calheta

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Calheta

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The image features a charming stone structure with an orange, sloped roof, reflected in the tranquil waters of a heated pool. Colorful stained glass elements adorn the entrance, complemented by planters and a palm tree nearby, all set against a serene blue sky.
Villa in Estreito da Calheta
4.95 out of 5 average rating, 218 reviews

Casa Palheiro @ 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)!

Top guest favorite
An outdoor seating area is highlighted by a decorative pillow featuring a floral design, resting against a woven chair. In the background, the infinity pool overlooks the expansive blue Atlantic ocean, framed by a clear sky.
Home in Tábua
4.95 out of 5 average rating, 130 reviews

Old Wine Villa

Welcome to Paradise! Come stay at our cozy Villa with a splendid Atlantic ocean view by the infinity pool! This house was first built in 1932 and since then it has been know as "Casa do Vinho Velho", "The Old Wine House". My great-grand mother used to tell stories about the old man "Vinho Velho" and his passion for his wine and agriculture. The house has been updated but we have kept old features, like an old brick oven in the kitchen and 3 stone rocks for vine hanging in the living room!

Top guest favorite
An outdoor dining area features a wooden table set with dishes and plants, surrounded by a few chairs. The rustic orange exterior of the adjacent building complements the lush greenery. The sea view can be seen in the background under an overcast sky.
Home in Arco Da Calheta
4.93 out of 5 average rating, 107 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. 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.

Top guest favorite
A bright exterior space is shown with a round pool surrounded by a wooden deck. Sun loungers in green and umbrellas provide shaded areas. Colorful gardens with tropical plants encircle the house, which features large glass doors leading into an indoor living area.
Home in Arco da Calheta
4.98 out of 5 average rating, 195 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

Top guest favorite
A yurt is positioned amidst vibrant yellow flowers, set against a backdrop of lush greenery. The coastline and a winding road are visible in the distance, with the ocean meeting a partly cloudy sky, creating a serene and natural landscape.
Yurt in Ponta do Sol
4.97 out of 5 average rating, 418 reviews

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

Top guest favorite
A stone exterior of the house is shown, featuring red trim that contrasts against the grey walls. A small bistro table with two chairs is positioned on the stone patio. Lush green grass and flower beds, along with a railing, overlook a vast view of the Atlantic Ocean under a clear blue sky.
Home in Arco da Calheta
4.98 out of 5 average rating, 102 reviews

Endless Blue House

Endless Blue is a traditional stone house, with modern improvements. It has a panoramic view over the Atlantic Ocean. It stands in a popular location for people who like to spend time in a quiet and peaceful place. It offers a suite, with a very beautiful sea view. The property also has outdoor leisure areas with excellent sun exposure throughout the day. It benefits from a large salt water swimming pool (10mX4m), where you can enjoy a spectacular sunset.

Guest favorite
A private balcony features wooden flooring and modern furnishings, including a small table and chairs. A sliding glass door offers views into a comfortably furnished living area, while lush greenery enhances the outdoor space. The surrounding landscape is visible under a clear blue sky.
Cabin in Jardim do Mar
4.96 out of 5 average rating, 125 reviews

Woodlovers Jardim® (Heated Pool Optional) - Unit 1

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
A modern wooden structure is featured, showcasing a private terrace that offers views of the ocean. The natural wood siding complements the serene surroundings, while a stone pathway leads up to the entrance. Clear skies enhance the tranquil coastal atmosphere.
Apartment in Jardim do Mar
4.94 out of 5 average rating, 316 reviews

Uni AIR Studio

Uni AIR is our top floor studio with a balcony that directly overlooks the horizon and the island's shore. Decorated with a bohemian feel, with a bamboo arch holding a dreamcatcher above the bed, this studio has a double bed,a fully equipped kitchen and an ensuite bathroom ensuring all the privacy and tranquility one is seeking. Feel like being on top of it all? Follow the steps up to Uni AIR's private terrace and let yourself enjoy the surroundings.

Top guest favorite
An infinity-edge pool is illuminated at night, reflecting the starry sky and ocean beyond. Surrounding tropical plants provide a lush backdrop, while a wooden deck extends around the pool, enhancing the tranquil ambiance and offering comfortable seating areas nearby.
Apartment in Paul do Mar
4.99 out of 5 average rating, 209 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
An outdoor area presents a heated saltwater pool framed by vibrant green grass and blooming shrubs. A single lounge chair is positioned beside the pool, with the expansive ocean visible in the background under a clear blue sky. Sunlight reflects off the water's surface.
Apartment in Jardim do Mar
4.99 out of 5 average rating, 136 reviews

☀️ 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, south facing balcony with ocean and pool view (24° to 26° Celsius). Guests have full access to the garden and heated saltwater pool.

Guest favorite
An infinity pool offers panoramic ocean views, bordered by a well-maintained garden featuring blooming flowers and lush greenery. Sun loungers are positioned nearby for relaxation, while a shaded terrace area can be seen in the background, enhancing the tranquil ambiance.
Villa in Ponta do Sol
4.97 out of 5 average rating, 149 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!

Top guest favorite
The image captures a view of Casa Nambebe, with a terracotta roof and surrounded by lush banana trees. An inviting infinity pool reflects the blue ocean, while the rugged coastline and greenery enhance the tranquil setting. The house is positioned on a hillside overlooking the sea.
Home in Ponta do Sol
4.99 out of 5 average rating, 181 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

Popular amenities for Calheta rentals with a pool

Quick stats about vacation rentals with a pool in Calheta

  • Total vacation rentals

    Explore 150 vacation rentals in Calheta

  • Nightly prices starting at

    Calheta vacation rentals start at G$14,646 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,610 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Calheta vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Calheta rentals

  • 4.9 Average rating

    Calheta stays are highly rated by guests—averaging 4.9 out of 5!

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