
Holiday rentals in Estreito da Calheta
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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.

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.

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.

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.

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.

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

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.

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.

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.

Incredible views, saltwater pool, and BBQ
Elegant and cozy house with incredible views and a pool, perfect for moments of rest and exclusivity. The spacious and bright spaces, comfortable beds and thoughtful details create a relaxing atmosphere for families or groups. It has free private parking, ensuring total convenience. The swimming pool and stunning views make this house the ideal setting for a memorable vacation.

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.

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.

Glamping Maracujá: Oasis Paradise
*Fast Wi-Fi! Download: 78.3 Mbps, Upload: 91.6 Mbps *Large balcony: 30m² *Barbecue area *Hot tub at 38°C *Fully equipped kitchen *Free parking 10 meters away *Free coffee and tea *Air-conditioning *Shampoo and shower gel *Bathrobes *Bluetooth speaker *Hair dryer
Popular amenities for Estreito da Calheta holiday rentals
Stay near Estreito da Calheta's top sights
Other great holiday rentals in Estreito da Calheta

Eco 1-bedroom house @ Casas Da Vereda

Villa Rada, by Pausa Holiday Rentals

Secluded Sunset Villa on Cliff & 180° Ocean Views

Vi Naturae Glamping - Sea View Dome

Exceptional luxury villa in Madeira | Bellissima

Villa Nóbrega

Sweet Paradise

Sun&Salt | Ocean view
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.
Destinations to explore
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- Family-friendly rentals Estreito da Calheta
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- Rentals with a patio Estreito da Calheta
- Praia do Porto do Seixal
- Monte Palace Tropical Garden
- Madeira Botanical Garden
- Zona Velha
- Casino da Madeira
- Praia da Calheta
- Ponta do Sol Beach
- Porto Moniz Natural Swimming Pools
- Praia Machico
- Complexo Balnear do Lido
- Cabo Girão
- Pico Do Areeiroo
- PR 11 - Vereda dos Balcões
- Casas Tipicas de Santana
- Fish Market
- Blandy's Wine Lodge
- Sé do Funchal
- Ponta do Pargo
- Santa Catarina Park
- Funchal Cable Car
- Cristo Rei
- CR7 Museum
- Cascata Dos Anjos
- Clube de Golf Santo da Serra





