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House holiday rentals in Estreito da Calheta

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Quick stats about house rentals in Estreito da Calheta

  • Total holiday rentals

    Explore 120 holiday rentals in Estreito da Calheta

  • Nightly prices starting at

    Estreito da Calheta holiday rentals start at $53 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,350 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Estreito da Calheta holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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 house rentals in Estreito da Calheta

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Fajã da Ovelha

Casa do Terrāço - Quinta Falcões do Sol

Casa Terrãço is a restored stone house that combines the unique charm of a centuries-old structure with modern comfort. The house features an open floor plan on the first level with a fully equipped kitchen and living space that offers ocean views through a big glass door. The top floor contains a spacious bedroom that opens to a large private terrace, providing breathtaking views of the ocean. Outside you will have a private area with a fire pit and access to the shared heated saltwater pool.

4.94 out of 5 average rating, 69 reviews
Top Guest favourite
Home in Estreito da Calheta

View Sun & Serenity Studio • Ocean View & Terrace

Welcome to View Sun & Serenity Studio, a peaceful studio in Arco da Calheta with breathtaking Atlantic Ocean views. Relax on the sunny terrace, enjoy outdoor dining, and unwind in one of Madeira's sunniest locations. Ideal for couples looking for comfort, space, privacy and unforgettable moments together. An ideal base for exploring Madeira, with Calheta Beach, the marina, restaurants and supermarkets just a short drive away, while the island's main express road is only one minute away.

5.0 out of 5 average rating, 6 reviews
Top Guest favourite
The exterior of Quinta das Rosas showcases a newly renovated two-story yellow building with a welcoming entrance. Surrounding greenery adds a refreshing touch, while a stone pathway leads to the door. A few pumpkins rest on the lawn, complementing the vibrant atmosphere during sunset.
Home in Estreito da Calheta

Quinta das Rosas 5 Amazing Seaview Trekking Beach

Quinta das Rosas has been completly renovated and open to guests in September 2022. The house first construction dates early 1930's and belonged to Mr. Manuel da Rosa who was my Grandmother's neighbour and the Village only store owner. My Grandmother Rosa and his wife Rosa were friends, reason I hounor the property by calling it "Quintas das Rosas". Its unbeatable location offers just 5 minutes from the best sandy beach of the island "Calheta Beach" and it is only 30 minutes from Funchal.

4.95 out of 5 average rating, 110 reviews
Guest favourite
A modern villa is showcased with clean architectural lines and large glass windows, surrounded by a manicured lawn featuring palm trees. An outdoor dining table and chairs are arranged on a patio adjacent to the heated infinity pool, overlooking scenic views of the landscape.
Home in Arco da Calheta

Panoramic View: Lux 3 bed w/ heated pool

Stunning modern villa with a private, heated infinity pool, 3 bedrooms and bathrooms, enjoying sea & mountain views. Located in one of the most sought-after areas with the best weather in the South West of Madeira island, the villa is unique in that it has a dedicated entertainment floor. Situated 5 mins away from Calheta Beach with its excellent restaurants on the marina & the same distance from Madalena do Mar beach. The house enjoys sun on the pool area from late morning until sunset.

4.97 out of 5 average rating, 113 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, 119 reviews
Guest favourite
A modern kitchen is presented, featuring sleek black countertops and white cabinetry. Stainless steel appliances, including a refrigerator and microwave, are visible. A bowl of fresh fruit is placed on the counter, and large glass doors lead to a balcony with scenic views.
Home in Arco da Calheta

Top View House

Top View House is a house with two bedrooms, a living room, a kitchen, two bathrooms, two balconies, and air conditioning. Located in a quiet neighborhood surrounded by nature with breathtaking views. Close to Levada Nova and hiking trails (Rabaçal, 25 Fontes, Lagoas da Dona Beja and Lagoas do Vento), also 10 minutes (by car) from a yellow sand beach, the Mudas Museum of Contemporary Art of Madeira, a supermarket, restaurants, bakeries, emergency services, and a pharmacy.

4.99 out of 5 average rating, 274 reviews
Superhost
A modern living area features a spacious sectional sofa adorned with decorative pillows. Natural light floods the room through large glass doors, revealing a glimpse of the outdoor space. A sleek kitchen is visible in the background, complemented by contemporary cabinetry.
Home in Arco da Calheta

Refúgio do Lourinho 2 - Relax in Nature

Casa Refúgio do Lourinho 2 is the ideal home for those who love nature and love hiking. Nestled in the mountains, this house has excellent sun exposure, comfort, tranquility, a modern style inside and everything you need for an unforgettable vacation. The location of the house is a few meters from one of our famous "levadas" (irrigation channels) and that allows you to discover our island. Our yellow sand beach is 6 km away and the nearest supermarket is 2 km away.

4.9 out of 5 average rating, 104 reviews
Top Guest favourite
A bright exterior space is shown with a round pool surrounded by a wooden deck. Sun loungers in green and umbrellas provide shaded areas. Colorful gardens with tropical plants encircle the house, which features large glass doors leading into an indoor living area.
Home in Arco da Calheta

Casa Sol e Vista

Villa with a nice view and good sunshine throughout the day. The house is located in one of the best areas of the parish. Dispoe with two bedrooms, living room / kitchen and two bathrooms, with lot for 6 people. The house is located on top of a hill, which gives it an extraordinary view. Outside there is a barbecue, a large garden and the swimming pool. Absolute tranquility. Come spend a pleasant vacation at CASA SOL E VISTA. Contact Duarte Paulo

4.98 out of 5 average rating, 207 reviews
Top Guest favourite
An outdoor dining area is displayed, featuring a table set with orange cloth and breakfast items including fruits and pastries. Behind the table, chairs are arranged neatly. A hammock is visible in the backdrop, with a panoramic view of the ocean and hills beyond.
Home in Arco da Calheta

Villa Bisa Atlantic View ,heated pool

A 2 bedroom villa located in Arco da Calheta. the property has 2 modern style bedrooms, 2 and a half luxurious modern bathrooms,outdoor shower ,new modern kitchen, living room, etc... The property has just been renovated,modern decorated with high quality furniture which is extremely comfortable. The villa also includes cable ,Satellite TV and internet. The property on the outside has BBQ ,pool with a panoramic Seaview ,a nice eating area.

4.97 out of 5 average rating, 159 reviews
Top Guest favourite
Home in Arco da Calheta

Eco Fajã Villas - Deluxe - 60m above sea level

High above the coastline is a private sanctuary where luxury meets nature. With sweeping panoramic sea views, a larger heated infinity pool, and an expansive garden, this villa is designed for those who seek space, tranquility, and exclusivity. Its sleek open-plan interiors, flooded with natural light, blend seamlessly with the outdoors, creating an effortless flow between modern comfort and Madeira’s breathtaking landscape.

5.0 out of 5 average rating, 6 reviews
Top Guest favourite
The image captures a view of Casa Nambebe, with a terracotta roof and surrounded by lush banana trees. An inviting infinity pool reflects the blue ocean, while the rugged coastline and greenery enhance the tranquil setting. The house is positioned on a hillside overlooking the sea.
Home in Ponta do Sol

Typical house above the sea

"Casa Nambebe" is a typical Madeiran house. Situated on the south slope of Madeira island, it is a great place to relax and enjoy a beautiful view of the sea. The house is placed in the middle of a land of banana trees where the contact with nature is immediate and the infinite pool will have you feel like you're in the ocean. Every sunset is unique. Número de licença ou registo 38381/AL

4.99 out of 5 average rating, 201 reviews
Top Guest favourite
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

Popular amenities for Estreito da Calheta house rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top Guest favourite
An infinity pool reflects the vibrant hues of a sunset over the ocean. The surrounding terrace features minimalistic railings, emphasizing unobstructed views of the coastal landscape and the sky's dramatic colors.
Home in Arco da Calheta

Syso House

4.95 out of 5 average rating, 132 reviews
Top Guest favourite
An outdoor seating area is highlighted by a decorative pillow featuring a floral design, resting against a woven chair. In the background, the infinity pool overlooks the expansive blue Atlantic ocean, framed by a clear sky.
Home in Tabua

Old Wine Villa

4.95 out of 5 average rating, 150 reviews
Guest favourite
A stone exterior of the house is shown, featuring red trim that contrasts against the grey walls. A small bistro table with two chairs is positioned on the stone patio. Lush green grass and flower beds, along with a railing, overlook a vast view of the Atlantic Ocean under a clear blue sky.
Home in Arco da Calheta

Endless Blue House

4.97 out of 5 average rating, 115 reviews
Guest favourite
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 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

4.94 out of 5 average rating, 116 reviews
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, 172 reviews
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

4.98 out of 5 average rating, 103 reviews
Guest favourite
The image displays a serene swimming pool reflecting the vibrant colors of the sky at sunset. A wooden deck surrounds the pool, with lounge chairs positioned for relaxation. The landscape features lush greenery in the background, enhancing the tranquil ambiance.
Home in Arco da Calheta

Casa Cro | Ocean View

4.94 out of 5 average rating, 204 reviews

Weekly house rentals

Top Guest favourite
Home in Arco da Calheta

Hilltop Hideaway by Escape to Madeira

5.0 out of 5 average rating, 30 reviews
Top Guest favourite
Home in Estreito da Calheta

2BR Villa, Hot Tub, Sea Views, garden & Office/BR

5.0 out of 5 average rating, 27 reviews
Guest favourite
A private heated pool reflects the serene colors of the sunset, set against a backdrop of the ocean. A wooden deck surrounds the pool, complemented by glass railings for an unobstructed view of the landscape.
Home in Arco da Calheta

A&M House II

5.0 out of 5 average rating, 51 reviews
Guest favourite
Home in Arco da Calheta

Stunning 3BR Villa | Ocean-View, Private Pool

4.9 out of 5 average rating, 20 reviews
Top Guest favourite
A serene outdoor space features a small table with two chairs, set for an evening meal. The horizon is illuminated by a sunset, casting warm colors over the ocean and distant landscape, while a grassy area surrounds the seating, enhancing the tranquil ambiance.
Home in Arco da Calheta

Abreu's House

5.0 out of 5 average rating, 62 reviews
Guest favourite
Home in Estreito da Calheta

Sea View Villa with Private Natural Lagoon Pool

4.94 out of 5 average rating, 17 reviews
Guest favourite
A unique swimming pool is partially embedded within rock formations, featuring crystal-clear water that reflects the bright blue sky above. Natural light filters through, creating a serene atmosphere in this inviting space.
Home in Campanario

Villas Calhau da Lapa 10

4.98 out of 5 average rating, 55 reviews
Superhost
A traditional Madeiran house is set against a backdrop of dramatic mountains under a colorful sky. The stone structure is surrounded by lush greenery and features a spacious terrace, allowing for stunning views of the natural landscape.
Home in Serra de Água

Madeira's last hidden mountain paradise!

4.83 out of 5 average rating, 87 reviews

Private house rentals

Guest favourite
A serene infinity pool overlooks the ocean, reflecting the blue sky and sunlight. Two glasses filled with a pink drink are positioned on a rustic wooden table, accompanied by a bottle. Lush greenery and hills are visible in the background.
Home in Arco da Calheta

Tropical Garden 4

4.97 out of 5 average rating, 62 reviews
Top Guest favourite
Home in Estreito da Calheta

Luxury Ocean View Villa | Pool I Calheta I Madeira

4.98 out of 5 average rating, 46 reviews
Guest favourite
A sun lounger with colored cushions is positioned on a spacious balcony, offering panoramic sea views. A decorative table sits nearby, and an adjustable sun canopy provides shade. The light-colored tiled floor enhances the bright, open feel of the space against a clear blue sky.
Home in Estreito da Calheta

Beautiful Villa With Panoramic Ocean Views

4.96 out of 5 average rating, 85 reviews
Guest favourite
Home in Madeira

Casa Levada - Sea View House

4.78 out of 5 average rating, 65 reviews
Superhost
Home in Arco da Calheta

Amazing views, saltwater pool, and BBQ

4.85 out of 5 average rating, 20 reviews
Top Guest favourite
A dining area with a round table is surrounded by four orange chairs. The scene features large glass windows providing a stunning view of a sunset over the ocean. Soft lighting reflects off decorative glasses arranged on the table.
Home in Ponta do Sol

Loriano Angels' Solar

4.98 out of 5 average rating, 55 reviews
Top Guest favourite
A modern infinity pool overlooks a stunning sunset illuminating the horizon. The pool's water reflects warm tones, creating a serene ambiance. Surrounding hills and rooftops are visible in the background, enhancing the tranquil coastal setting.
Home in Ponta do Sol

Casa da Lombada

5.0 out of 5 average rating, 57 reviews
Top Guest favourite
Home in Estreito da Calheta

Casa Piquita

4.95 out of 5 average rating, 21 reviews

Destinations to explore