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$12,550 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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Guest favorite

A private infinity pool is set against a backdrop of the ocean, surrounded by lush tropical plants. Comfortable seating, featuring blue cushions, faces the pool and ocean views, creating a relaxing outdoor space. The bright sky enhances the tranquil atmosphere.

Home in Funchal

4.95 out of 5 average rating, 115 reviews

Seafront Home in Old Town Funchal w Pool & Garden

Beachfront design home featured in Conde Nast Traveller w private pool & tropical garden in Old Town of Funchal. A stunning oasis just 5min walk to city center, beach & restaurants. Free street parking, fast internet & strong AC. 2 bedroom historic villa with 2 WC´s, living room & kitchen w sea views. Stylish interiors & lots of outside relaxing, sunbathing & dining area with BBQ. Tropical villa that feels like the countryside w amazing climate. Perfect base to explore Madeira´s hikes & beaches

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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, 113 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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Top guest favorite

A dining area features a set table with plates, glasses, and bottles against a warm yellow wall. A cozy sleeping space is visible in the background, showcasing a spacious bed with a patterned blanket and soft lighting from wall-mounted fixtures. A comfortable sofa is also present.

Home in Ribeira Brava

4.94 out of 5 average rating, 173 reviews

Two Birds Place - Mar, Sol e Natureza!

Casa solarenga, vista mar, situada no sul (centro da ilha). Acesso rápido para qualquer parte da ilha. Próxima do mar e das caminhadas pela natureza. Espaço amplo para 2 pessoas com possibilidade de mais 1. Todas as comodidades para ótimo descanso, inclui Ar Condicionado, Biblioteca "Take a book, return a book" Estacionamento gratuito em frente ao AL. Beneficie também da espreguiçadeira, chuveiro, churrasco ou mesa exterior. Poderá também lavar o seu material de caminhada ou mesmo o veículo.

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Superhost

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

4.87 out of 5 average rating, 244 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

An aerial view reveals a tropical house surrounded by lush banana plantations, with the ocean and pebbled beach visible in the distance. Nearby houses are set against the backdrop of rugged cliffs, showcasing a blend of natural beauty and coastal charm.

Home in Madalena do Mar

4.97 out of 5 average rating, 218 reviews

Tropical house :) 2 min to the sea, views, nature

Tropical house :) - renovada recentemente, tudo é novo e fresco - ar condicionado na sala - 2 minutos para a praia (50 metros) e estacionamento fácil - vista mar e sunsets deslumbrantes - varanda e pátio privados para refeições no exterior - cozinha totalmente equipada - (forno, máquina de lavar a loiça, microondas, máquina de lavar a roupa, etc) - Internet rápida, smart TV e coluna bluetooth - excelente localização (acesso fácil a toda a ilha, caminhadas e praias) - Check in autónomo

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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.

ViewBeachGrill

Top guest favorite

A spacious bedroom is shown, featuring a modern bed and a lamp positioned beside it. Large windows provide views of the ocean and a cliff-side pathway leading down toward the water. The coastline and bridge are visible in the background.

Condo in Gaula

4.86 out of 5 average rating, 168 reviews

Magnificent Oceanfront Luxury | AC & Free Parking

Acorda com o som relaxante das ondas e a sensação única de estar num cruzeiro de luxo. Aqui, o mar é a tua vista e o teu vizinho! O que te espera: 👉 Espetáculo constante de navios no teu horizonte. 👉 Wi-Fi ultrarrápido 1 GB Wi-Fi 👉 Ar condicionado em todas as divisões 👉 Garagem gratuita. 👉 Localização a 10 min do Funchal e 7 min do aeroporto 👉 Acesso direto à via rápida que te levará a qualquer parte da ilha Reserva já o teu refúgio exclusivo de luxo à beira-mar!

BeachViewLocation

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, 133 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.

ViewBeachGetting around

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

4.98 out of 5 average rating, 159 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.

BeachViewOutdoor spaces

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!

ViewLong stayWifi

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.

BeachViewParking

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, 151 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

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