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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 ﺩ.ﺇ 220 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 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, 117 reviews
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

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!

4.94 out of 5 average rating, 137 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

“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!

4.87 out of 5 average rating, 248 reviews
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

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, 119 reviews
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

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!

4.86 out of 5 average rating, 174 reviews
Guest favorite
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, 110 reviews
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

☀️ 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. Two minute walk to the promenade and Portinho beach.

4.98 out of 5 average rating, 162 reviews
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 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
Top guest favorite
An expansive view of the Atlantic Ocean is presented from the edge of a private infinity pool. The tranquil waters reflect the clear blue sky above, while rolling hills and the coastline of Camara de Lobos are visible in the background.
Home in Câmara de Lobos

Peak A Boo (Private Heated Pool & Private Parking)

Take it easy at this unique and tranquil getaway with breathtaking views. The interior design with large sliding glass panels offers a real alfresco feeling for those balmy Madeiran days and nights. The exterior terrace with private infinity heated pool is a true balcony over the Atlantic Ocean glamorously charming the bay just under your eyes.

5.0 out of 5 average rating, 101 reviews
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 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, 158 reviews
Top guest favorite
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, 219 reviews
Top guest favorite
A sunlit terrace features two lounge chairs positioned for relaxation against a backdrop of a stunning ocean view. A small table is placed between the chairs, complemented by a potted plant. The surrounding landscape includes lush green hills and a distant coastline.
Home in Madalena do Mar

Atlantic View II

É um alojamento com uma fantástica vista para o mar! Muito agradável, com todas as comodidades, localizado numa zona privilegiada da ilha, com clima temperado todo o ano, tudo para ter umas ferias maravilhosas e inesquecíveis.

4.99 out of 5 average rating, 215 reviews

Popular amenities for Estreito da Calheta waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Guest favorite
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, 149 reviews
Top guest favorite
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, 218 reviews
Top guest favorite
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, 194 reviews
Guest favorite
Apartment in Arco da Calheta

Geremoise

4.83 out of 5 average rating, 196 reviews
Top guest favorite
A balcony offers breathtaking views of the ocean and surrounding landscape. A small table, adorned with a floral arrangement and fresh fruit, is set between two chairs. A soft aqua blanket rests on one chair, inviting relaxation in the gentle coastal breeze.
Apartment in Caniço

Ferienwohnung mit traumhaftem Meerblick

5.0 out of 5 average rating, 118 reviews
Guest favorite
A dining table on the balcony features a yellow tray with pastries and beverages, creating an inviting breakfast setting. Scenic views of the ocean and landscape are visible in the background, with a sparkling blue pool below and lush greenery surrounding the area.
Apartment in Ponta do Sol

Villa Smiling Petals (Nest Four) Pool & Sea View

4.96 out of 5 average rating, 115 reviews
Top guest favorite
A balcony is featured with two comfortable chairs and a small table, set against a backdrop of a sunset over the ocean. The pool area and surrounding landscape are visible, enhancing the tranquil ambiance.
Apartment in Funchal

Infinity Pool & Amazing Sunset Ocean View

4.99 out of 5 average rating, 113 reviews
Guest favorite
The sunny terrace features two loungers positioned for optimal ocean views, showcasing the Atlantic Ocean and Desertas Islands in the distance. A table is present for dining or relaxation, with smooth, neutral surfaces and glass railings offering a clear perspective of the serene landscape.
Apartment in Caniço

Vista Mar – Apartment with Terrace & Sea View

4.93 out of 5 average rating, 233 reviews

Waterfront house rentals

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, 113 reviews
Top 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

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

4.97 out of 5 average rating, 222 reviews
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

2-Bedroom house by the sea with Patio

4.92 out of 5 average rating, 113 reviews
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

Seafront Home in Old Town Funchal w Pool & Garden

4.94 out of 5 average rating, 117 reviews
Top guest favorite
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

4.94 out of 5 average rating, 116 reviews
Top guest favorite
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, 119 reviews
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

Relax Over The Sea -12391/AL

4.98 out of 5 average rating, 103 reviews
Guest favorite
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, 196 reviews

Waterfront condo rentals

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, 135 reviews
Guest favorite
Condo in Madalena do Mar

Penthouse Marina Sol 20785/AL

4.94 out of 5 average rating, 109 reviews
Guest favorite
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, 298 reviews
Top guest favorite
Condo in Funchal

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

4.9 out of 5 average rating, 209 reviews
Top guest favorite
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, 146 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, 159 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, 189 reviews
Guest favorite
Condo in Funchal

Monumental Apartment

4.86 out of 5 average rating, 173 reviews

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