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Vacation rentals with a pool in Estreito da Calheta

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Top-rated rentals with a pool in Estreito da Calheta

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
A large heated saltwater pool is set against a backdrop of ocean and mountain views, framed by modern glass doors. Sunlight reflects off the water, enhancing the tranquil atmosphere. Spacious terraces surrounding the pool provide ample space for relaxation.
Villa in Arco da Calheta
4.96 out of 5 average rating, 100 reviews

Villa Lara, sea views, heated Pool A/C

Villa Lara is a fabulous modern single story three bedroom villa in the sought after area of Arco da Calheta. Lovely ocean and mountains views, sun terraces with a large private heated salt water pool and space for outside dining. There is an open plan fully fitted kitchen with a dining table for formal dining, leading to a comfortable sitting area with television with sliding doors leading outside. Facilities include aircon, heating, WIFI and parking. Approx. 10 minutes to Calheta beach. Fabulous spacious, light and modern 3 bedroom villa thoughtfully designed to maximize sun exposure and privacy. Fully fitted kitchen with all the required equipment to make you feel like you're at home. Large master bedroom with luxurious en-suite bathroom. Hot and cold air conditioning throughout, large heated swimming pool with ample sun terraces and garden area for relaxing or for children to run around. Alojamento Local License Number: 114112/AL We are at your disposal to help or answer your questions. We're contactable at any time via our mobile or by email. We will do our very best so you have a wonderful stay! Villa Lara is located centrally in Arco da Calheta with access to local amenities including various supermarkets, cafes, bars, restaurants and a pharmacy. Approx 10 minutes drive from the Villa and you'll be at Calheta Beach where you can enjoy the golden sand, several restaurants and book whale and dolphin watching tours. Villa Lara is ideal for couples, solo adventurers, families (with kids (cot & highchair can be provided)), and big groups. Villa Lara is set in a peaceful location ideal for walking the levadas (unmissable walks in Calheta include Paul da Serra, Rabacal (to Risco Waterall & 25 Fontes), Levada Nova and the Prazeres to Paul do Mar walk) and is close to a bus route. The property is approximately 30 minutes drive to Funchal and 45 minutes from the airport. A car is recommended so you can explore the island at your convenience. If you wish to book a private transfer with our local partners, please contact us in advance (which will be cheaper than taking a taxi direct from the airport).

Guest favorite
The outdoor area features a private infinity pool with steps leading in, surrounded by a spacious deck with sun loungers. Palm trees provide shade, while a cozy seating arrangement in vibrant blue invites relaxation. The modern structure showcases large glass windows reflecting the sunny ambiance.
Home in Funchal
4.94 out of 5 average rating, 103 reviews

Pirate House Funchal seafront home w Pool & garden

Beach front home featured in Conde Nast Traveller w private swimming pool & tropical garden in the Old Town of Funchal. Just 200m, 5min walk to the city center, beach & restaurants. Free street parking & fast internet. 2 bedroom villa w 2 bathrooms, living room & kitchen w unlimited sea views. Fully renovated w stylish interiors & lots of outside relaxing, sunbathing & dining space with BBQ. Tropical oasis in the city, feels like the countryside. Perfect base to explore Madeira´s hikes & beaches

Guest favorite
The image captures a wooden-roofed structure situated beside a calm sea, with expansive views of the coastline and towering rocky cliffs under a clear blue sky. The serene waters glisten in the sunlight, providing a striking contrast to the natural landscape.
Place to stay in Jardim do Mar
4.95 out of 5 average rating, 276 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
A spacious bed is centered in the room, adorned with decorative pillows and a colorful blanket. Nightstands are positioned on either side, each featuring soft lighting. A decorative straw hat and a bright flower are placed on the bed, enhancing the serene atmosphere.
Villa in Estreito Calheta
4.94 out of 5 average rating, 158 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)!

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 secluded orange tent is positioned against a stunning sunset over the ocean. Vibrant colors fill the sky, with clouds gently illuminated. Lush greenery surrounds the tent, providing a sense of intimacy with nature in a tranquil, elevated setting.
Yurt in Ponta do Sol
4.97 out of 5 average rating, 639 reviews

Papaia Yurt ~ EcoGlamping 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 modern stone-walled pool area features a turquoise water surface with a gentle waterfall. Sun loungers are positioned neatly alongside the pool, surrounded by lush greenery and ornamental grasses, creating a serene outdoor environment.
Cottage in Jardim do Mar
4.96 out of 5 average rating, 191 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.

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, 137 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.

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, 193 reviews

Meu Pé de Cacau - Studio Papaya 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
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, 150 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!

Popular amenities for Estreito da Calheta rentals with a pool

Quick stats about vacation rentals with a pool in Estreito da Calheta

  • Total vacation rentals

    Explore 130 vacation rentals in Estreito da Calheta

  • Nightly prices starting at

    Estreito da Calheta vacation rentals start at G$4,187 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,830 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Estreito da Calheta vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Estreito da Calheta rentals

  • 4.8 Average rating

    Estreito da Calheta stays are highly rated by guests—averaging 4.8 out of 5!

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