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Waterfront holiday rentals in Estreito da Calheta

Find and book unique waterfront accommodation on Airbnb

Quick stats about waterfront rentals in Estreito da Calheta

  • Total holiday rentals

    Explore 30 holiday rentals in Estreito da Calheta

  • Nightly prices starting at

    Estreito da Calheta holiday rentals start at $84 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,560 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Holiday 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 holiday 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 accommodation in Estreito da Calheta

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious terrace features a smooth wooden surface and a white railing, providing unobstructed views of the coastline and ocean. Sunlight bathes the area, highlighting the natural landscape of hills and the sea in the background.
Villa

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

5.0 out of 5 average rating, 113 reviews
Guest favourite
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

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

4.97 out of 5 average rating, 218 reviews
Guest favourite
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

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.

4.93 out of 5 average rating, 118 reviews
Guest favourite
A comfortable living area is displayed, featuring a sectional gray sofa and a coffee table with a decorative glass vase. A flat-screen television is mounted on the wall, and framed artwork adds a subtle touch to the contemporary space.
Home in Estreito da Calheta

Refúgio do Tibéu II

O Refúgio do Tibéu II, é uma casa privada, acabada de construir no ano de 2023, fica situada numa área muito tranquila e repleta de sol. É o local ideal para umas férias a dois ou até mesmo em família. Fica próximo de inúmeros lugares turísticos, incluindo a fantástica praia do concelho. A sua localização facilita os seus passeios pela ilha, seja ao mar ou às montanhas, e ou pelas levadas da ilha. Esperamos por si para visitar a nossa casa nesta bela ilha.

4.94 out of 5 average rating, 108 reviews
Guest favourite
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

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.

4.93 out of 5 average rating, 111 reviews
Guest favourite
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

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!

4.97 out of 5 average rating, 161 reviews
Top Guest favourite
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 Arco da Calheta

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.

4.95 out of 5 average rating, 144 reviews
Guest favourite
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 Tabua

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

4.99 out of 5 average rating, 154 reviews
Superhost
An outdoor terrace is surrounded by lush banana plants, offering a scenic view of the ocean. Comfortable seating options are positioned on the tile floor, complemented by a glass railing that enhances the openness of the space. A clear blue sky provides a bright backdrop.
Holiday home in Arco da Calheta

Jacinta Guest House | Ocean View

Casa com excelente exposição solar com vista pacífica e deslumbrante sobre o mar e montanha. A casa está dividida em 2 apartamentos T2, mas pode ser utilizada como casa inteira. Cada andar possui de 2 quartos de dormir, 1 casa de banho, cozinha e sala.

4.88 out of 5 average rating, 115 reviews
Top Guest favourite
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

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

4.98 out of 5 average rating, 103 reviews
Top Guest favourite
A charming stone house features a warm exterior with a pink trim. Wooden chairs are positioned near the entrance, while a staircase leads to the upper level. The surrounding area includes a garden that adds to the natural setting.
Home in Arco da Calheta

STONE HOUSE

Esta casa é a simbiose entre o passado tradicional das gentes e da ilha e a reconstrução actual e versátil. Acomoda 4 pessoas. Situada sobre a praia e a vila, goza de tranquilidade e bons acessos a "Levadas", "veredas" e à Floresta Laurissilva.

4.94 out of 5 average rating, 116 reviews
Top Guest favourite
A sunny space features a splash pool surrounded by well-maintained grass and tropical plants. White walls contrast with dark volcanic rock in the background. A covered outdoor dining area is visible, providing a shaded space for meals while enjoying the outdoors.
Cottage in Arco da Calheta

Villa Papaya

An Outstanding Location, with a Fabulous View. Splash Pool and a Table to do meals outside. Unforgetable Sunset, with the sea and the Marina View! Villa Papaya Address: Rua Serra D’Água - Vereda do Morgadinho N. º 24 9370-076 Arco da Calheta

4.98 out of 5 average rating, 218 reviews

Popular amenities for Estreito da Calheta waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment accommodation

Guest favourite
A private jacuzzi is positioned outdoors, offering scenic views of the sea and surrounding greenery. Bright blue skies enhance the tranquil atmosphere, while the clean lines and modern design of the jacuzzi contribute to a serene outdoor retreat.
Apartment in Ribeira Brava

Renala I "With Jacuzzi" by PAUSA Holiday Rentals

4.93 out of 5 average rating, 148 reviews
Guest favourite
An outdoor area features a wooden dining table shaded by a large umbrella, accompanied by wooden chairs. A small pool is enclosed by a deck, with steps leading into the water. Lush green grass surrounds the space, complemented by cacti and lanterns for ambiance.
Apartment in Ponta do Sol

CASA 61 (private pool) by Stay Madeira Island

4.99 out of 5 average rating, 103 reviews
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

Beautiful Views - Apartment Fontes

4.87 out of 5 average rating, 245 reviews
Top Guest favourite
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

☀️ Bright & Spacious w/ Pool & Oceanside View :D

4.98 out of 5 average rating, 160 reviews
Top Guest favourite
A balcony with a circular table and two metal chairs overlooks the sea. A bottle of sparkling wine rests in an ice bucket, accompanied by two glasses and a plate of strawberries. The vibrant blue water stretches into the distance beneath a clear sky.
Apartment in Câmara de Lobos

Stunning Ocean View Apartment

4.99 out of 5 average rating, 215 reviews
Guest favourite
Apartment in Jardim do Mar

Uni AIR Studio

4.94 out of 5 average rating, 337 reviews
Top Guest favourite
A well-equipped kitchen features wooden cabinetry and a granite countertop. A dining table set for four is visible, with a bowl of fresh fruit and a bottle placed on a decorative tray. Large glass doors open to a scenic view of the ocean and surrounding landscape.
Apartment in Arco da Calheta

Casa Linhares

4.95 out of 5 average rating, 192 reviews
Superhost
Apartment in Arco da Calheta

Geremoise

4.83 out of 5 average rating, 195 reviews

Waterfront house rentals

Guest favourite
A tranquil scene captures the reflection of vibrant greenery in a serene pond. Surrounding the water, various tropical plants and flowers provide a lush backdrop to the recently restored house, characterized by its stone structure and warm red exterior. Sunshine enhances the inviting atmosphere.
Home in Estreito da Calheta

Casa do Penique ORGANIC

4.85 out of 5 average rating, 168 reviews
Guest favourite
Home in Ribeira Brava

Madeira Pearl: Breathtaking Atlantic Ocean Views

4.94 out of 5 average rating, 107 reviews
Guest favourite
The charming stone property features a welcoming entrance with a terracotta roof and vibrant green doors. A small outdoor seating area with a table and chairs is set amidst lush plants and blooming flowers along the pathway, creating an inviting atmosphere.
Home in Arco da Calheta

Recanto das Florenças (2) – Great Views & Sunsets

4.91 out of 5 average rating, 195 reviews
Superhost
A spacious living area features a comfortable sectional sofa and a large rug on the floor. Floor-to-ceiling glass doors provide unobstructed views of the sea. Two woven light fixtures hang from the ceiling, enhancing the bright atmosphere.
Home in Funchal

The View, Funchal

4.93 out of 5 average rating, 110 reviews
Top Guest favourite
Aerial view of the modern residence, showcasing its proximity to the coastline. The surrounding area features a mix of greenery and traditional homes, with the ocean visible in the background. The landscape highlights the tranquil setting by the sea, offering a serene environment.
Home in Jardim do Mar

CasaMar

4.97 out of 5 average rating, 116 reviews
Guest favourite
A charming exterior view of a pink house with stone accents is shown. A dark stone table is placed on a pebble pathway, surrounded by tropical plants. Large windows offer glimpses of the interior, and a sloped roof adds character to the structure.
Home in Paul do Mar

CASA DA LEVADA NOVA - Paul do Mar

4.96 out of 5 average rating, 113 reviews
Top Guest favourite
The exterior of a stone house features a garden with green grass, bordered by flower beds and fruit trees. The building showcases multiple windows with red accents, surrounded by a hillside landscape under a clear blue sky.
Home in Corujeira

Quinta da Tabua

4.99 out of 5 average rating, 144 reviews
Guest favourite
A wooden lounge chair is positioned on a balcony, overlooking a scenic view of the Atlantic Ocean. The landscape features a charming church with a bell tower, surrounded by coastal architecture and hills in the distance, under a partly cloudy sky.
Home in Ponta Delgada

Casa Abreu bright and stylish, sea, nature & relax

4.9 out of 5 average rating, 371 reviews

Waterfront condo accommodation

Top Guest favourite
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

Magnificent Oceanfront Luxury | AC & Free Parking

4.86 out of 5 average rating, 170 reviews
Superhost
A balcony area features two wicker chairs and a matching coffee table, overlooking the ocean. The sun rises above the horizon, reflecting on the water and creating a warm glow. The railing provides an unobstructed view of the serene seaside and sky.
Condo in Paul do Mar

Surfside apartment in the heart of Paúl do Mar

4.82 out of 5 average rating, 132 reviews
Top Guest favourite
Condo in Madalena do Mar

Penthouse Marina Sol 20785/AL

4.94 out of 5 average rating, 108 reviews
Top Guest favourite
Condo in Funchal

360° Sea & City views, in the heart of Funchal

4.9 out of 5 average rating, 206 reviews
Superhost
A spacious living area is presented, featuring a dining table with six chairs and a wooden sideboard. A television is positioned on a matching console. Warm wooden flooring enhances the bright, inviting space, while indoor plants and decorative items add a subtle touch of greenery.
Condo in Funchal

Lovely seaside apartment in Funchal

4.84 out of 5 average rating, 158 reviews
Guest favourite
A spacious terrace is showcased with light wooden beams and a tiled floor, featuring a large dining table surrounded by comfortable chairs. Potted plants add greenery, while stunning views of the Atlantic Ocean and Funchal skyline can be seen in the background.
Condo in Funchal

Atlantic View Penthouse

4.84 out of 5 average rating, 295 reviews
Top Guest favourite
A spacious terrace features a glass railing with views of the ocean and surrounding landscape. Lush greenery is visible below, along with a pool area. Mountains frame the horizon, adding depth to the serene coastal scenery.
Condo in Funchal

New dream luxury appartment in the Madeira Palace.

4.99 out of 5 average rating, 145 reviews
Superhost
A balcony overlooking the ocean is showcased, featuring a small table and two chairs. Soft curtains allow natural light to enhance the space. The sea and distant landscape are visible, complemented by greenery and rooftops in the foreground.
Condo in Funchal

Bright Seafront Apartment

4.82 out of 5 average rating, 187 reviews

Destinations to explore