Vacation rentals with a pool in Estreito da Calheta

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Top-rated rentals with a pool in Estreito da Calheta

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Guest favorite

An infinity pool extends into the horizon, providing an uninterrupted view of the blue ocean. The sky is adorned with soft clouds, reflecting a serene atmosphere. The merging of water and sky creates a seamless visual continuity, inviting relaxation and contemplation.

Place to stay in Jardim do Mar

4.94 out of 5 average rating, 221 reviews

Uni EARTH Studio

This gorgeous, bright studio overlooks the breathtaking hills of Madeira Island thanks to it also having floor to high windows,that give you a real sense of freedom and nature.The studio accommodates 2 people, who have access to a unique and quirky ensuite bathroom, a fully equipped kitchen and a delightful garden allowing you to further indulge yourself in the Uni experience. 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

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, 214 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, 123 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!

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, 189 reviews

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

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, 128 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 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.

Guest favorite

Home in Arco Da Calheta

4.92 out of 5 average rating, 105 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

The modern villa is set atop gently sloping terrain, with expansive windows and wooden accents. Surrounding greenery enhances the landscape, and a private turquoise pool can be seen below. A terrace with seating options is also visible, inviting relaxation amid the natural surroundings.

Cabin in Jardim do Mar

4.96 out of 5 average rating, 121 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.

Top guest favorite

A spacious two-story building is featured, surrounded by a well-kept garden. An outdoor swimming pool reflects the evening light, while seating areas are visible nearby. Lush greenery and local stone are integrated throughout the landscape, providing a peaceful retreat.

Villa in Fajã da Ovelha

4.97 out of 5 average rating, 143 reviews

Quinta São Lourenço ≈≈≈ Casa Lagar ≈≈≈

The « Quinta São Lourenço » is a traditional Madeiran property of 3 000 m² from the 19th century, renovated into independent houses. The Quinta is an ideal holiday destination and is well known for its dominant position on the Atlantic Ocean, its beautiful flower garden and its shared outdoor swimming pool. Let yourself be surprised by the majestic sunsets and take a break with the roar of the Ocean.

Top guest favorite

An infinity pool stretches over a wooden deck, with views of the expansive Atlantic Ocean and dramatic cliffs. Sunlight reflects off the water's surface, enhancing the serene atmosphere. Surrounding greenery complements the natural setting, inviting relaxation and contemplation.

Apartment in Paul do Mar

4.98 out of 5 average rating, 186 reviews

Meu Pé de Cacau - Studio Papaia 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.

Guest favorite

The image depicts a modern villa complex with two distinct houses, one built of stone and the other in a vibrant color. An infinity pool reflects the sky and is surrounded by lush gardens and pathways, creating a relaxing outdoor environment.

Villa in Ponta do Sol

4.97 out of 5 average rating, 145 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

A stone house with traditional architecture is framed by lush banana trees. In the foreground, a spacious pool reflects the sky, accompanied by two sun loungers under a shaded umbrella. The surrounding terrace is paved, creating an inviting outdoor space for relaxation.

Home in Ponta do Sol

4.99 out of 5 average rating, 174 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

Guest favorite

Apartment in Calheta

4.95 out of 5 average rating, 111 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.