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Waterfront vacation rentals in Estreito da Calheta

Find and book unique waterfront rentals on Airbnb

Quick stats about waterfront rentals in Estreito da Calheta

  • Total vacation rentals

    Explore 30 vacation rentals in Estreito da Calheta

  • Nightly prices starting at

    Estreito da Calheta vacation rentals start at G$12,568 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,560 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 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!

Top-rated waterfront rentals in Estreito da Calheta

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A stunning hillside view captures the sparkling sea reflecting sunlight, framed by lush, green mountains. Palm trees are visible in the foreground, providing a sense of tranquility. The rooftops of nearby houses are dispersed throughout the landscape, enhancing the scenic coastal environment.
Villa in Madeira
5 out of 5 average rating, 112 reviews

House with stunning views surrounded by nature

Countryside house, located on a hill with the best view over Madalena do mar. Recanto of the sea is located in the warm and sunny municipality of Ponta do Sol, in a privileged area with excellent sun exposure and sea views. The property has a stunning view from any room in the house. The house has 2 bedroom. One with a double bed and one with 2 single beds ; 2 bathroom; a fully equipped kitchen and a fully equipped indoor barbecue. The maximum capacity is 6 guests. Número de registo:152419/AL

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Guest favorite
A charming outdoor space features a wooden pergola draped with sheer curtains, providing shade over a hot tub. Nearby, a seating area with dark wicker furniture is set against a backdrop of vibrant greenery and blooming flowers, along with a few white lounge chairs.
Apartment in Lombo Do Doutor
4.88 out of 5 average rating, 242 reviews

Beautiful Views - Apartment Fontes

“Beautiful Views – Apartment Fontes” is a peaceful retreat in the quiet hills of Calheta, created for travelers who value nature, comfort, and authentic island living. Surrounded by open views and fresh air, it’s the perfect base for levada walks, hiking, and exploring Madeira and close to the sea. Ideal for nature lovers seeking calm, space, and a true sense of the island. If you’re looking for more than just a place to sleep, a place to breathe, reset, and feel the island , you’ve found it!

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Guest favorite
A charming exterior view of the Cottage Pearl showcases a stone facade with blue window shutters. The landscaped garden features comfortable lounge chairs, a gazebo with draped fabric, and vibrant flowers, all framed by surrounding hills. Soft outdoor lighting enhances the inviting atmosphere.
Cottage in Paul do Mar
4.94 out of 5 average rating, 135 reviews

Cottage Pearl-Rural Holiday Experience by SeaPearl

Discover the "Cottage Pearl" in the warmest and most tropical region of Madeira. The accommodation is the result of a rural tourism project called "SeaPearl", inspired by the sea, in which a house and a haystack were rehabilitated, maintaining its rural aspect and original characteristic, with a touch of modernity, simplicity and all the comfort. This sublime cottage has a private jacuzzi, solarium with sea view, barbecue, vegetable garden, trees and garden.An authentic appeal to your senses!

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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, 118 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.

ViewBeachGetting around

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, 336 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.

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Superhost
A small balcony offers a view of the sea, framed by greenery and a decorative nature-inspired wall piece. A comfortable blue sofa is situated nearby, inviting relaxation while enjoying the surroundings.
Apartment in Funchal
4.93 out of 5 average rating, 199 reviews

Blue

Excelente localização / Great location Excelente vista / Great view PT: Elegante e confortável apartamento no coração do Funchal (Praça da Autonomia). Vista panorâmica para o mar e para a encosta do Funchal. Muito próximo de todas as comodidades e pontos de interesse. EN: Elegant and comfortable apartment in Funchal’s heart (Praça da Autonomia). Panoramic view of the sea and Funchal's hillside. Very close to all amenities and points of interest.

ViewBeachHospitality

Top guest favorite
An outdoor patio area features comfortable seating on light-colored cushions, alongside a coffee table. Potted plants add greenery against a backdrop of natural stone, creating a serene space. Steps lead up to additional levels, inviting exploration of the surrounding landscape.
Home in Lombo Do Doutor
4.94 out of 5 average rating, 109 reviews

2-Bedroom house by the sea with Patio

Enjoy yourself while staying in this newly built house located near Calheta's Beach, only a 2-minute walk. Our place offers 2 bedrooms, 3 bathrooms, kitchen, living room and a solarium. Perfect for small families or couples looking for a place to relax while close to the beach and mountains at the same time. Includes also private parking and proximity to supermarket, restaurants, cafés and to Calheta's Marina.

ViewRiverGetting around

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, 160 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!

ViewFamilyShared spaces

Top guest favorite
The image shows a spacious infinity pool extending towards the ocean, with lounge chairs positioned on the deck. The serene blue water reflects the sky, creating a seamless visual. A seating area is visible in the background, enhancing the outdoor space.
Apartment in Calheta
4.95 out of 5 average rating, 143 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.

BeachViewGrill

Top guest favorite
The spacious balcony features two loungers facing unobstructed ocean views. The vibrant blue sea meets the horizon, with palm trees lining the shoreline. A bright sky with scattered clouds enhances the serene outdoor setting.
Home in Jardim do Mar
4.81 out of 5 average rating, 139 reviews

The Yellow House

The Yellow House - can’t get closer to the sea and waves in Jardim Do Mar than this three story villa with 2 large bedrooms and 2 bathrooms. Total privacy large balcony off the main bedroom. Also sun deck off middle floor with open floor plan living room and kitchen with amazing unobstructed ocean/waves view from every level. Come enjoy the sun, waves and sunsets!

ViewBeachAir conditioning

Guest favorite
A dining table is set for four, overlooking a serene ocean view. Glassware and dinnerware are arranged neatly, while a jacuzzi is visible in the foreground. The sunset creates a warm ambiance, enhancing the overall tranquil setting.
Hut in Tábua
4.99 out of 5 average rating, 150 reviews

Glamping Maracujá: Oasis Paradise

*Wi-Fi rápido! Download: 78.3 Mbps, Upload: 91.6 Mbps *Varanda ampla: 30m² *Área de churrasco *Jacuzzi quente a 38°C *Cozinha totalmente equipada *Estacionamento gratuito a 10 metros *Café e chá gratuito *Ar condicionado *Shampoo e Gel de banho *Roupões *Coluna de som bluetooth *Secador para cabelo

BeachViewCheck-in

Guest favorite
A spacious infinity pool overlooks the coastline and ocean, surrounded by sun loungers and palm trees. The house features large glass doors that provide stunning views of the surrounding landscape. The tranquil setting highlights the connection between the property and its natural surroundings.
Home in Ponta do Sol
4.98 out of 5 average rating, 101 reviews

Relax Over The Sea -12391/AL

Beautiful spacious villa perched on the cliff top, stunning views of the Atlantic Ocean, its swimming pool with infinite plane over the ocean provides fantastic and relaxing moments for larger families in the sunniest located part of the island

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Popular amenities for Estreito da Calheta waterfront rentals