Some info is shown in its original language. Translate

Holiday rentals in Estreito da Calheta

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Estreito da Calheta

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top guest favourite
Home in Santana
5 out of 5 average rating, 242 reviews

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.

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

Villa Rada, by Pausa Holiday Rentals

This stylish two-level villa features three bedrooms, each with its own private bathroom, plus an additional guest WC. The open-plan interior offers a bright, welcoming atmosphere with air conditioning and contemporary design. Outside, enjoy a private pool, barbecue area, comfortable sun loungers, and an outdoor dining area, all set against stunning sea and mountain views. Located in a peaceful area of the island, it’s the perfect place to relax and experience Madeira in comfort and style.

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
4.97 out of 5 average rating, 114 reviews

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.

Top 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
4.98 out of 5 average rating, 104 reviews

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.

Guest favourite
A modern tent structure is nestled among lush greenery, showcasing a geometric design. Natural vegetation surrounds the tent, with wooden steps leading up to the entrance. The clear blue sky complements the inviting atmosphere of this serene outdoor retreat.
Tent in Achadas da Cruz
4.83 out of 5 average rating, 806 reviews

Be adventurous , something completely different 2

Located in the north-western part of the island ,its an amazing location protected by conservation laws that have kept the area free of over development. With epic mountain and sea-views (the photos don't do it justice) the tents are located 450m above the coastline. If a place to relax and unwind is what you after then this would be the place to come to. There are also some amazing levada walks to explore in the area.There are three tents on the property so you might neighbours.

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
4.98 out of 5 average rating, 203 reviews

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

Top guest favourite
A secluded orange tent is positioned against a stunning sunset over the ocean. Vibrant colors fill the sky, with clouds gently illuminated. Lush greenery surrounds the tent, providing a sense of intimacy with nature in a tranquil, elevated setting.
Yurt in Ponta do Sol
4.97 out of 5 average rating, 676 reviews

Papaia Yurt ~ EcoGlamping in a Hidden Paradise

Wake up in total privacy, surrounded by a lush permaculture garden where you can see, taste, and smell nature’s abundance. At Canto das Fontes, in the sunny Sítio dos Anjos, it feels like eternal spring all year — even when other parts of Madeira are cooler. An award-winning regenerative eco-glamping where sustainability meets comfort and luxury, with a natural pool, Honesty Bar, and stunning views of the sea and waterfall. 💧🌿 More pictures and vibes: @cantodasfontes

Top guest favourite
A coastal home is positioned on a hillside with panoramic views of the ocean. A well-maintained garden with neatly arranged stepping stones leads to the entrance. The vibrant green foliage contrasts with the tranquil blues of the sea and sky.
Tiny home in Fajã da Ovelha
4.96 out of 5 average rating, 74 reviews

Casa das Moirinhas

Um sonho tornado realidade. Um antigo palheiro cuidadosamente transformado num refúgio junto ao oceano, com vistas amplas sobre o Atlântico e sobre a vila do Paul do Mar. Inserida num caminho real, a Casa das Moirinhas está pensada para quem procura a tranquilidade e o contacto com a natureza, numa envolvência única. Onde o azul do oceano encontra o verde profundo das montanhas, criando um ambiente sereno e inspirador, ideal para desligar, abrandar e relaxar.

Superhost
An outdoor dining area is set up under a wooden gazebo, featuring a large table surrounded by metal chairs. A picturesque view of the ocean and cliffs is visible in the background, illuminated by the warm glow of sunset. The space includes decorative lights strung overhead.
Villa in Seixal
4.92 out of 5 average rating, 181 reviews

Madeira Black Sand House by Stay Madeira Island

Stay Madeira Island presents Madeira Black Sand Beach House! Set on the north coast of Seixal beach, Madeira Black Sand Beach House offers a dream view towards the black sand and the deep blue sea surrounded by green cliffs. This century old stone house has been with the same family for 30 years and was used as a weekend second home. The owners decided to share this unique spot with the world and the refurbished plan had the guest's comfort in mind.

Top guest favourite
Home in Faja da Ovelha
4.92 out of 5 average rating, 50 reviews

Casa do Terrāço - Quinta Falcões Do Sol

Casa Terrãço is a restored traditional 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 unobstructed ocean views through a three-meter glass door. The top floor contains a spacious bedroom that opens to a large private terrace, providing breathtaking views of the ocean.

Top guest favourite
An infinity pool stretches over a wooden deck, with views of the expansive Atlantic Ocean and dramatic cliffs. Sunlight reflects off the water's surface, enhancing the serene atmosphere. Surrounding greenery complements the natural setting, inviting relaxation and contemplation.
Flat in Paul do Mar
4.99 out of 5 average rating, 213 reviews

Meu Pé de Cacau - Studio Papaia in Paúl do Mar

Meu Pé de Cacau is a tropical fruit garden surrounded by dramatic cliffs to the north-east and the vast Atlantic Ocean to the south-west. Four beautifully designed and sustainably built studios share the property with an infinity pool, social areas and luxurious plantations hosting hundreds of different tropical fruits, planted on traditional agricultural terraces hand crafted in basalt stone.

Guest favourite
A private heated swimming pool is set within a modern exterior. Clear blue water glistens under the sun, surrounded by sleek glass railing. Views of greenery and the distant sea can be seen beyond the pool, contributing to a serene outdoor environment.
Villa in Arco da Calheta
4.93 out of 5 average rating, 216 reviews

Stylish 3BR Villa with Heated Pool & Views

Modern 3-bedroom villa in sunny Arco da Calheta with sea & mountain views. Enjoy a private heated pool, BBQ terrace, fast Wi-Fi, and secure garage. Walk to restaurants and cafés, 10 minutes by car to Calheta Beach and 30 minutes to Funchal. Ideal for couples, families, or groups — the perfect base to explore Madeira.

Popular amenities for Estreito da Calheta holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Estreito da Calheta?

    Estreito da Calheta has more than 220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cottage rentals in Estreito da Calheta?

    Experience the best of Estreito da Calheta with our cottage rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Estreito da Calheta?

    Four-legged friends are welcome in Estreito da Calheta. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Estreito da Calheta?

    Yes! Work meets play with ease at over 90 vacation rentals in Estreito da Calheta featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Estreito da Calheta vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 150 vacation homes with pools in Estreito da Calheta, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Estreito da Calheta have air conditioning?

    Absolutely! We offer over 20 apartment rentals with air conditioning in Estreito da Calheta. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Estreito da Calheta have a kitchen?

    Absolutely! We offer over 60 villa rentals with a kitchen in Estreito da Calheta. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Estreito da Calheta have wifi?

    Absolutely! We offer over 110 house rentals with wifi in Estreito da Calheta. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Estreito da Calheta have free parking?

    Absolutely! We offer over 110 house rentals with free parking in Estreito da Calheta. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Estreito da Calheta?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 90 homes with wifi, over 20 homes with air conditioning, over 70 homes with free parking, over 80 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Estreito da Calheta

  • Total holiday rentals

    Explore 310 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 11,170 verified reviews to help you choose

  • Family-friendly holiday rentals

    220 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    150 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    310 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!

Destinations to explore

  1. Airbnb
  2. Portugal
  3. Madeira
  4. Estreito da Calheta