
House holiday rentals in Estreito da Calheta
Find and book unique houses on Airbnb
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 $39 SGD per night before taxes and fees

Verified guest reviews
Over 4,170 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
110 of Estreito da Calheta holiday rentals include wifi 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 house rentals in Estreito da Calheta
Guests agree: these houses are highly rated for location, cleanliness and more.

NEW! Madeira's last hidden mountain paradise!
Welcome to On the Rocks, your off-grid retreat where serenity meets full seclusion. Surrounded by the soothing sounds of cascading waterfalls, unwind with panoramic views that stretch across the horizon. Nestled in the heart of the island (15 min to both coasts), with hiking trails at your doorstep, you’re perfectly positioned to explore or relax. Whether seeking adventure or sun-soaked relaxation, this peaceful sanctuary offers the perfect balance—a home base to discover or a haven to recharge.

Casinha da Beatriz
Olá! Somos a Sónia, Élio e a nossa filha Beatriz. O nosso objetivo é tornar as vossas férias inesquecíveis!! Sejam bem vindos à nossa casa!! A "casinha da Beatriz" está localizada em Santana, terra das casas típicas, ex-libris e cartaz turístico da ilha da Madeira. Eram casas compostas por um sotão, onde se guardavam os produtos agrícolas, e piso térreo com a área habitacional. Reconstruímos uma destas "casinhas"típicas, datada de 1950, com todo o conforto dos tempos atuais. Tem vista mar/serra.

Stunning 3BR Villa | Ocean-View, Private Pool
Atlantic View by Costa Living – a peaceful and spacious ocean-view villa in Arco da Calheta. This freshly renovated and newly furnished 3-bedroom home (sleeps 9) features a private pool, panoramic Atlantic and mountain views, balcony, and modern open-plan living. Enjoy fast Wi-Fi, Smart TV, fully equipped kitchen, laundry and private garage. Set among nature and hiking trails, just minutes from Calheta Beach, Madalena do Mar Beach, and cafés. Perfect for families and friends. Car required.

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.

CasaMar
Procura um lugar para relaxar com conforto à beira mar, ou para continuar o seu trabalho de forma online? Este poderá ser o lugar que procura. Desfrute as suas férias numa casa moderna, localizada a 100m da praia em zona calma, soalheira e quente. Assim como moderna, é muito prática com um layout simples. Nela existe um bonito escritório, onde poderá concluir o seu trabalho num clima sossegado, e com excelente conecção á internet. Perfeito para quem tem intenções de trabalhar e relaxar.

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.

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

Chalet Ladeira
Refúgio rústico com churrasqueira. Fuja da rotina e venha relaxar neste encantador chalet no meio da natureza. Rodeado por paisagens verdes e pelo silêncio do campo, este espaço foi pensado para quem procura descanso, conforto e momentos especiais. O chalet combina o charme rústico da madeira com todo o conforto necessário para uma estadia tranquila. Aqui poderá acordar com o som dos pássaros, tomar o pequeno-almoço ao ar livre e aproveitar o ar puro e a calma que só o campo oferece.

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.

Casa Caboz
Casa Caboz is an elegant residence, ideal for those seeking comfort and tranquility. With a spacious backyard and a barbecue, it is the perfect place to enjoy outdoor moments while taking in the stunning views of the sea and sunset. The cozy atmosphere guarantees a unique and relaxing experience. Located in Canhas, Ponta do Sol, just 8 minutes from the village center, it is the perfect retreat for those who wish to explore the island or simply relax in a paradise-like setting.

Casa Sol e Vista
Moradia com boa vista e bom sol durante todo o dia. A casa está localizada num dos melhores locais da freguesia. Dispoe de dois quartos de dormir, sala / cozinha e duas casas de banho, com lotaçao para 6 pessoas. A casa esta situada no cimo de uma colina o que faz com que a casa tenha uma vista extraordinaria. No exterior tem um churrasco, um grande jardim e a piscina. Absoluta tranquilidade. Venha passar umas férias agradaveis na CASA SOL E VISTA. Contactar Duarte Paulo

Eco Fajã Villas - Retreat - 60m above sea level
Perched above the coastline, this villa offers a harmonious blend of comfort and nature. With beautiful sea views, a heated infinity pool, and a generous garden, the villa invites you to slow down and soak in Madeira’s natural charm. Thoughtfully designed open-plan interiors allow light to pour in, connecting the indoor spaces with the surrounding landscape for a relaxed, effortless stay. Ideal for those looking for quiet, space, and a touch of understated luxury.
Popular amenities for house rentals in Estreito da Calheta
House rentals with a pool

Casa da Lombada

The Sunset Avenue w/infinity pool(optional heated)

Villa Nóbrega

Pereira´s Domus

Old Wine Villa

Moradia Syso

Typical house above the sea

Bella Vista (Heated Pool & Private Parking)
Weekly house rentals

Sun&Salt | Ocean view

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

Casa Refúgio M

Villas Calhau da Lapa 10

Hilltop Hideaway by Escape to Madeira

Villa Panorama - Luxury Villa with Jacuzzi-Calheta

Ocean Garden House - Flat

NEW Quinta da Luz - By Your Madeira Rentals
Private house rentals

Casa Sameiro

Villa Vella Panorama View

Cardais Paradise View

Sunset

Mouras House, Lovely place!

Peak A Boo (Private Heated Pool & Private Parking)

Tabua Lodge

The One Madeira
Destinations to explore
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- Pet-friendly rentals Estreito da Calheta
- Beachfront rentals Estreito da Calheta
- Rentals with a patio Estreito da Calheta
- Rentals with a firepit Estreito da Calheta
- Rentals with a washing machine and dryer Estreito da Calheta
- Flat rentals Estreito da Calheta
- Rentals with a hot tub Estreito da Calheta
- Rentals with pools Estreito da Calheta
- Villa rentals Estreito da Calheta
- Waterfront rentals Estreito da Calheta
- Family-friendly rentals Estreito da Calheta
- Rentals with beach access Estreito da Calheta
- Chalet rentals Estreito da Calheta
- Cottage rentals Estreito da Calheta
- Rentals with a fireplace Estreito da Calheta
- Beach house rentals Estreito da Calheta
- Rentals with outdoor seating Estreito da Calheta
- House rentals Portugal
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- Madeira Botanical Garden
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- Casino da Madeira
- Zona Velha
- Praia da Calheta
- Ponta do Sol Beach
- Praia Machico
- Porto Moniz Natural Swimming Pools
- Complexo Balnear do Lido
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- Cabo Girão
- PR 11 - Vereda dos Balcões
- Pico Do Areeiroo
- Sé do Funchal
- Fish Market
- Madeira Whale Museum
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- Funchal Cable Car
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- CR7 Museum





