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Holiday rentals in Estreito da Calheta

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Estreito da Calheta

  • Total holiday rentals

    Explore 320 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 11,780 verified reviews to help you choose

  • Family-friendly holiday rentals

    210 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    140 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    320 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 holiday rentals in Estreito da Calheta

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

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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
4.84 out of 5 average rating, 80 reviews

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.

Guest favourite
Home in Arco da Calheta
4.94 out of 5 average rating, 17 reviews

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.

Guest favourite
A glimpse of the exterior of the unique dome tents is provided, surrounded by lush greenery and tropical plants. A wooden walkway leads through the garden area, offering access to the tents while showcasing the natural landscape nestled among the hills.
Tent in Achadas da Cruz
4.87 out of 5 average rating, 770 reviews

Be adventurous , something completely different

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 have neighbours.

Top guest favourite
A private deck offers an expansive view of the ocean, surrounded by lush greenery. A dining table and chairs are positioned under a shaded pavilion, providing a perfect spot for relaxation. The area combines natural beauty with a tranquil atmosphere.
Cottage in Faja da Ovelha
5 out of 5 average rating, 49 reviews

Casa Mar - Quinta Falcões do Sol [Falcões do Sol Farm]

Casa Mar offers a blend of historical architecture and modern comfort. This fully restored traditional stone house features a private 25 square meter deck with dining table, alongside a lower private lounge area. Large glass doors provide an incredible view of the sea and allow for a natural flow between the indoor and outdoor spaces. The property has a big heated saltwater infinity pool for all our guests on the property to enjoy with the most beautiful view on the ocean.

Guest favourite
A yurt is positioned amidst vibrant yellow flowers, set against a backdrop of lush greenery. The coastline and a winding road are visible in the distance, with the ocean meeting a partly cloudy sky, creating a serene and natural landscape.
Yurt in Ponta do Sol
4.97 out of 5 average rating, 462 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

Guest favourite
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, 186 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
A private outdoor balcony is featured, showcasing a hot tub surrounded by natural wooden decking. Comfy seating options, with soft cushions, are positioned nearby. The view beyond includes expansive ocean horizons and a bright blue sky with scattered clouds.
Tent in Prazeres
4.89 out of 5 average rating, 87 reviews

Soul Glamping |Luxury | Ocean | jacuzzi | nature

Soul Glamping is a luxury eco-retreat - unique in Madeira island - where 5 state-of-the-art domes are to be found in absolute harmony with the surrounding nature. Purposefully located in the island southwest, this Glamping Resort is home to the most beautiful sunsets of the planet. Secluded in nature with breathtaking views, Soul Glamping is tailored to nature loving individuals who seek pure magic, relaxation and absolute privacy.

Guest favourite
Home in Arco da Calheta
4.81 out of 5 average rating, 16 reviews

Incredible views, saltwater pool, and BBQ

Casa elegante e acolhedora, com vistas incríveis e piscina, perfeita para momentos de descanso e exclusividade. Os espaços amplos e luminosos, as camas confortáveis e os detalhes pensados ao pormenor criam um ambiente relaxante para famílias ou grupos. Dispõe de estacionamento privado gratuito, garantindo total comodidade. A piscina e as vistas deslumbrantes tornam esta casa o cenário ideal para férias memoráveis.

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, 221 reviews

Meu Pé de Cacau - Studio Papaya 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.

Superhost
An aerial view reveals two modern villas set within well-maintained gardens, featuring a private heated swimming pool and sun loungers. The terraced layout showcases a mix of greenery and stone pathways, seamlessly integrated into the surrounding landscape.
Villa in Estreito da Calheta
5 out of 5 average rating, 7 reviews

The Rock Villas

The Rock Villas proposes 3 bedrooms for up to 6 guests, and great facilities such as its private heated swimming pools and other luxurious pieces of equipment. The 2 recent constructions blend harmoniously in the cliffy landscape while offering large views over the Atlantic ocean: a peaceful and stylish getaway on the South West coast of the island of Madeira.

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
5 out of 5 average rating, 51 reviews

A&M House II

A&M House II, the perfect place to enjoy your best vacation on Madeira Island. Located in a quiet area with a mild climate, it offers guests all the comfort they need to feel at home. Its stunning views make every evening unforgettable with its stunning sunsets. Come discover Madeira and enjoy the comfort that A&M House II has to offer.

Guest favourite
A dining table is set for four, overlooking a serene ocean view. Glassware and dinnerware are arranged neatly, while a jacuzzi is visible in the foreground. The sunset creates a warm ambiance, enhancing the overall tranquil setting.
Hut in Tábua
4.99 out of 5 average rating, 150 reviews

Glamping Maracujá: Oasis Paradise

*Wi-Fi rápido! Download: 78.3 Mbps, Upload: 91.6 Mbps *Varanda ampla: 30m² *Área de churrasco *Jacuzzi quente a 38°C *Cozinha totalmente equipada *Estacionamento gratuito a 10 metros *Café e chá gratuito *Ar condicionado *Shampoo e Gel de banho *Roupões *Coluna de som bluetooth *Secador para cabelo

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 210 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 100 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 140 vacation homes with pools in Estreito da Calheta, available on Airbnb. Make a splash and soak up the sun in style!

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

    Absolutely! We offer over 30 villa 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 apartment rentals in Estreito da Calheta have wifi?

    Absolutely! We offer over 90 apartment rentals with wifi in Estreito da Calheta. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 10 cottage 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 House Rentals in Estreito da Calheta?

    Enhance your stay in our House Rentals with the most popular amenities: over 120 homes with a kitchen, over 40 homes with air conditioning, over 120 homes with wifi, over 110 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.