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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.

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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.

Top guest favourite
An infinity swimming pool is featured, merging seamlessly with the ocean view. Sun loungers are arranged on the nearby terrace, surrounded by tropical plants and palm trees. The clear blue sky enhances the serene atmosphere of the outdoor space.
Home in Funchal
4.94 out of 5 average rating, 109 reviews

Seafront Villa in Old Town Funchal w Pool & Garden

Beachfront design home featured in Conde Nast Traveller w private pool & tropical garden in the Old Town of Funchal. A stunning oasis just 5min walk to city center, beach & restaurants. Free street parking, fast internet & strong AC. Two bedroom historic villa with 2 WC´s, living room & kitchen w unlimited sea views. Stylish interiors & lots of outside relaxing, sunbathing & dining area with BBQ. Tropical villa that feels like the countryside. Perfect base to explore Madeira´s hikes & beaches

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
A modern living space showcases large glass doors that provide ample natural light and views of the surrounding area. A dark gray sectional sofa and a minimalist coffee table create a relaxing environment. A wooden staircase leads to the upper floor, complementing the contemporary design.
Home in Jardim do Mar
4.97 out of 5 average rating, 113 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
Tent in Achadas da Cruz
4.83 out of 5 average rating, 805 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 natural swimming pool is surrounded by lush greenery, featuring a stone edge and a thatched-roof area with a hammock nearby. The tranquil waters reflect the clear blue sky and the ocean in the distance, enhancing the sense of serenity in this scenic outdoor space.
Yurt in Ponta do Sol
4.97 out of 5 average rating, 449 reviews

Mango Yurt ~Eco-Glamping 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 Ba,r and stunning views of the sea and waterfall. 💧🌿 More pictures and vibes: @cantodasfontes

Top guest favourite
Tiny home in Fajã da Ovelha
4.96 out of 5 average rating, 73 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.

Guest favourite
An inviting infinity pool stretches along the cliffside, reflecting the blue ocean and sky. Two comfortable chairs are positioned nearby, surrounded by a natural landscape characterized by various plants and stone pathways. Soft sunlight illuminates the scene, enhancing the serene atmosphere.
Home in Faja da Ovelha
4.91 out of 5 average rating, 46 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 is illuminated at night, reflecting lights against the tranquil water. Surrounding plants add a touch of green, while the ocean stretches beyond, merging with the sky as the sun sets. A wooden deck enhances the serene outdoor space.
Flat in Paul do Mar
4.99 out of 5 average rating, 212 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.

Top guest favourite
A spacious terrace is featured, equipped with a wooden lounge chair and an expansive glass door that leads into the living area. Panoramic views of the ocean and surrounding landscape are visible, creating an open and airy atmosphere.
Flat in Prazeres
5 out of 5 average rating, 141 reviews

Belmont Charming Apartment

Belmont Charming with wonderful mountain and ocean view. Totally equipped, modern,cosy and with spacious terrace. Free wi-fi and car park. Stays 47km from the airport. It's a good starting point for many levada walks and for the natural swimming pools. The sea is 10 minutes away by car.

Popular amenities for Estreito da Calheta holiday rentals

Frequently Asked Questions

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

    Estreito da Calheta has more than 50 family-friendly villa rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Estreito da Calheta with our apartment rentals, starting at about $30 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 house rentals in Estreito da Calheta?

    Four-legged friends are welcome in Estreito da Calheta. Choose from more than 10 house rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 30 house rentals in Estreito da Calheta featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Yes! Dive into the perfect getaway at one of over 40 villa rentals 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 cottage rentals in Estreito da Calheta have a kitchen?

    Absolutely! We offer over 10 cottage rentals with a kitchen in Estreito da Calheta. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Estreito da Calheta have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Estreito da Calheta. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 50 villa 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 80 homes with a kitchen, over 70 homes with free parking, over 90 homes with wifi, over 20 homes with air conditioning, 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 $38 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