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Holiday houses 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

Beatriz's little house

Hello! We are Sonia, Elio and our daughter Beatriz. Our goal is to make your vacation unforgettable!! Welcome to our home!! The "Casinha da Beatriz" is located in Santana, land of typical houses, ex-libris and tourist poster of the island of Madeira. They were houses composed of an attic, where agricultural products were kept, and a ground floor with the living area. We rebuilt one of these typical "little houses," dating back to 1950, with all the comforts of today. It overlooks the sea/mountains.

Superhost
A serene outdoor space features a hot tub surrounded by lush greenery, with a comfortable lounge chair nearby. A wooden pergola provides shade, while the distant horizon is illuminated by a warm sunset, creating a tranquil environment for relaxation.
Apartment in Lombo Do Doutor
4.88 out of 5 average rating, 234 reviews

Beautiful Views - Apartment Fontes

“Beautiful Views – Apartment Fontes” is a peaceful retreat in the quiet hills of Calheta, created for travelers who value nature, comfort, and authentic island living. Surrounded by open views and fresh air, it’s the perfect base for levada walks, hiking, and exploring Madeira and close to the sea. Ideal for nature lovers seeking calm, space, and a true sense of the island. If you’re looking for more than just a place to sleep, a place to breathe, reset, and feel the island , you’ve found it!

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
Home in Ribeira Brava
4.98 out of 5 average rating, 52 reviews

Sweet Paradise

Um paraíso no coração da Zona Oeste da Madeira orientado a sul e com um pôr do sol fantástico. Zona residencial calma e com bons acessos. A 5min da praia, comércio e restaurantes e com uma ótima localização para explorar a ilha. Uma casa moderna com piscina de água salgada e aquecida (mediante pagamento), boas áreas, churrasqueira, zona de solário, jardim com ervas aromáticas, ginásio e estacionamento. Toda a casa é climatizada e com uma cozinha equipada para celebrar ótimos momentos.

Guest favourite
Tent in Achadas da Cruz
4.83 out of 5 average rating, 804 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.

Guest favourite
An infinity pool extends towards the horizon, reflecting the sky and the ocean. Lounge chairs are positioned nearby, offering views of the landscape below. A seamless glass barrier ensures unobstructed visuals of the sweeping vista of the coastline and sea.
Home in Câmara de Lobos
5 out of 5 average rating, 45 reviews

Villa Nóbrega

Discover the perfect getaway on Madeira Island! A luxury villa, designed to offer comfort and an unforgettable experience. With a prime location and incredible views of the city and the sea, it is ideal for sunrise lovers. The villa has a suite and two large bedrooms, all with air conditioning and a private balcony. It has an integrated living room and kitchen, infinity pool, garden, barbecue area and private garage. A perfect place to relax and create unique memories.

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

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.

Superhost
Home in Arco da Calheta
5 out of 5 average rating, 3 reviews

Zto Madeira Oceanfront Escape | Pool & Garden

Perched above the Atlantic in sunny Calheta, this private cliffside house is made for relaxing island escapes. Enjoy panoramic ocean views, a private pool, peaceful surroundings, and unforgettable sunsets from the garden. With 3 bedrooms, bright living spaces, outdoor dining areas, and nearby access to beaches, hikes, and restaurants, it’s the perfect Madeira getaway for families, couples, or friends seeking comfort, privacy, and sunshine year-round.

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

Casa das Moirinhas

A dream come true. An old haystack carefully transformed into a haven by the ocean, with sweeping views over the Atlantic and the village of Paul do Mar. Located on a royal road, Casa das Moirinhas is designed for those seeking tranquility and contact with nature in a unique setting. Where the blue of the ocean meets the deep green of the mountains, creating a serene and inspiring environment, ideal for switching off, slowing down and relaxing.

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
Apartment in Paul do Mar
4.99 out of 5 average rating, 226 reviews

Meu Pé de Cacau - Mango Studio in Paúl do Mar

Meu Pé de Cacau is a tropical fruit garden and island retreat 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.

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 $50 NZD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    310 of Estreito da Calheta holiday rentals include Wi-Fi 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