Cottage vacation rentals in Estreito da Calheta

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Top-rated cottage rentals in Estreito da Calheta

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Top guest favorite

A panoramic view displays the lush greenery of vineyards and gently sloping hills leading to a coastal town. The Atlantic Ocean glistens in the distance, while charming rooftops punctuate the landscape, framed by the mountains of Madeira. Clear skies enhance the scene.

Cottage in Estreito De Câmara

4.96 out of 5 average rating, 337 reviews

Palheiro do Covão cottage.

Cottage located by the mountains of Câmara de Lobos in Madeira Island, with a view to the Atlantic ocean and to the west coast of Funchal. The house is just for you and your companion. You will not have to share it with other persons. From June 2025: Now with a private parking spot in a flat area, about 250m from the house. Wifi internet in all the house. Cable TV service in the living room. Please read carefully all informations before booking. Here you can relax and connect with nature.

Top 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

4.93 out of 5 average rating, 120 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!

Top guest favorite

The exterior of the rustic house features a peach-colored facade with a tiled roof and circular windows. A warmly detailed wooden door provides entrance, while the clear blue sky and expansive ocean backdrop enhance the overall setting.

Cottage in Fajã da Ovelha

4.97 out of 5 average rating, 118 reviews

Ovelha do Sol · Cottage with Ocean View

At the Caminho de Sao Joao, about 600 m high above the coast of the fishing village Paul do Mar, lies our rustic country house Ovelha do Sol ("Sun Sheep"). Here you can relax as a couple, with family or friends in your own domicile with a breathtaking almost all-round sea view, fresh wideness and dreamlike sunsets. An ideal location to explore the rustic southwest of the flower island. The Levada Nova runs past only about 50 metres above and the road down the hill leads to the beach ...

Superhost

A scenic view of rolling hills covered with banana trees and a distant mountain landscape can be seen. The coastline features calm waters, while a green lawn with a wooden pergola is visible in the foreground. A clear sky enhances the tranquil atmosphere.

Cottage in Ponta do Sol

4.93 out of 5 average rating, 170 reviews

Tropical Lovers - Levada & Bananas cliff

A magnificent place with a superb view over the sea. In a locality known for banana trees plantation. Very quiet and pleasant you can find the beaches within 5min and all the other services you need. Perfect for resting and recuperating energies during your visits to the island. Near the house you will find a levada walk with great view over the fabulous mountainous landscapes of the west. The house is full of sunshine, natural light and good energy for you. Jacuzzi (extra fee 40€)

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, 184 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.

Guest favorite

A well-lit bedroom features a spacious bed adorned with decorative pillows. Large windows provide natural light and a view of palm trees and distant water, while a wooden ladder leans against the wall. Two rolled towels are neatly arranged on the bed.

Cottage in Madeira

4.94 out of 5 average rating, 172 reviews

Cork House By Fernandes’s Cottage - Madeira island

A modern and cosy apartment, close to the mountains and the sea, in the picturesque village of Ponta Delgada in Madeira Island. Perfect for a relaxing holiday or for working peacefully outdoors, ready to accommodate a family of 4 or two couples. Ideal location to explore the North Coast of the island but also at a short drive from the South Coast. On your return, at the end of the day, the property's refreshing swimming pool is waiting to help you recover.

Guest favorite

A sunset view is captured over the ocean, with hues of orange and yellow reflecting on the water's surface. In the foreground, a green shrub frames the scene, while a white railing provides a boundary, enhancing the peaceful ambiance of the natural setting.

Cottage in Ponta do Sol

4.92 out of 5 average rating, 146 reviews

Anjos Paradise Nook

Anjos Paradise Nook is a Studio, decorated with a special touch, designed to be the cozy place to return to after a day exploring our beautiful island. It features a fully equipped kitchen , a living room area, and on site parking, within walking distance of the amazing waterfall Cascata dos Anjos. Enjoy a swim in the pool and a meal in the garden at sunset, overlooking the horizon, in perfect communion with the Nature surrounding you.

Guest favorite

The exterior of a two-story house features a stone accent wall, complemented by colorful flowering plants in the garden. A cozy home office space is indicated, with bright seating visible. The roof showcases traditional tiles, and the surroundings include lush greenery.

Cottage in Estreito da Calheta

4.88 out of 5 average rating, 164 reviews

A Casinha Das Flores

This place is ideal for those who wish to completely disconnect from their routine, have the experience how life goes on in a traditional Madeira village and a memorable contact with nature. The landscapes present themselves in an unusual way throughout the day, no two glances the same. The Little House of Flowers is a typical house of Madeira, which has been sensitively restored to offer a cozy atmosphere to those who wish to stay.

Superhost

The stone cottage is framed by lush greenery and vibrant flowers, creating a serene entrance. The building features wooden shutters and a sloped roof, nestled in a natural landscape that offers a peaceful escape among the surrounding flora.

Cottage in Santana

4.88 out of 5 average rating, 359 reviews

Cedro - A cottage surrounded by nature!

Surrounded by forest and located up high in the mountains, Cedro cottage is the ideal choice for nature lovers, who seek peace and unique moments in the comfort of a well-equipped cottage. Its privileged location within the natural park of Ribeiro Frio, allows access to many "Veredas" and "Levadas", and reveals up close the beauty of the Laurissilva forest. Come, and enjoy a unique and romantic stay in this atlantic paradise!

Guest favorite

A spacious terrace features a wooden dining table surrounded by four comfortable chairs. Lush plants are positioned nearby, and the view showcases the sea and mountains in the distance under a clear sky. Sunlight brightens the area, creating an inviting outdoor space.

Cottage in Seixal

4.98 out of 5 average rating, 125 reviews

Casa da Pedra-Lage

This family house has more than 200 years old. Has been renovated and adapted to modern times respecting the traditional features but giving a touch of contemporary and comfort. It`s located in a area close to the sea and natural pools with views for the mountains. There are free public parking spaces next to the house