
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.

Magnificent Oceanfront Luxury | AC & Free Parking
Já imaginaste acordar com o som das ondas e sentires-te a bordo de um cruzeiro de luxo? Aqui, o Atlântico é a tua única fronteira e o teu único vizinho. O que te espera: 👉 Vista infinita e um espetáculo constante de navios no teu horizonte. 👉 Wi-Fi ultrarrápido 1 GB Wi-Fi 👉 Garagem gratuita. 👉 Localização a 10 min do Funchal e 7 min do aeroporto 👉 Acesso direto à via rápida que te levará a qualquer parte da ilha Reserva o teu lugar na primeira linha do oceano. O paraíso é aqui!

Casa do Terrāço - Quinta Falcões Do Sol
Casa Terrãço is a restored 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 ocean views through a big glass door. The top floor contains a spacious bedroom that opens to a large private terrace, providing breathtaking views of the ocean. Outside you will have a private area with a fire pit and access to the shared heated saltwater pool.

Secluded Sunset Villa on Cliff & 180° Ocean Views
Naturalis Villas, one of the best platforms for Madeira Villa Holidays Rental presents: Villa Miradouro is a secluded top of the cliff property with no direct neighbours, surrounded by extensive lush green gardens and a large 10 x 5 metre pool facing the ocean offering spectacular panoramic views and sunsets. Maid service is provided up to three days per week (subject to availability) to keep the property clean and spotless. The service includes cleaning, laundry, garden and pool maintenance.

NEW Quinta da Luz - By Your Madeira Rentals
Welcome to our Quinta da Luz holiday home for 4 that combines sustainable design, modern amenities, and stylish comfort. Relax in the infinity pool, practice yoga with sea views, or discover Madeira’s breathtaking nature on scenic hikes. The house features 2 bedrooms with king-size beds, 2 bathrooms with walk-in showers, a spacious living room, and an open, fully equipped kitchen with dining area. A large terrace with panoramic sea views invites you to unwind. Travel cot available on request.

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.

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.

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.

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

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.

Amazing luxury villa, panoramic sea view | Adagio
Nestled in a peaceful and serene location, this luxury contemporary villa in Madeira offers breathtaking sea views and elegant living spaces. The spacious open plan dining and living room features large picture windows that flood the space with natural light, seamlessly connecting the indoors to the outdoors. These windows open to a generous outdoor terrace, where you will find the swimming pool and can relax and enjoy the surrounding beauty.

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.

Villa with large pool and fantastic view
NEW :-) Swim your laps in the long pool. Enjoy the view of the Atlantic Ocean and lush nature while sitting in the garden. A very stylish place that is located in a small quiet village. To relax - but also to be active. Jogging, hiking and swimming - all possible right by the house. Restaurants can be reached in a few minutes by car. For work, there is a study and fast internet. End the day with a glass of rosé and the sunset.
Popular amenities for Estreito da Calheta holiday rentals
Stay near Estreito da Calheta's top sights
Other great holiday rentals in Estreito da Calheta

Chalet Ladeira

Madeira's last hidden mountain paradise!

MG House

Achadinha - Mountain Cottage - Away from it all!

Casa da Lombada

Top View Calheta: Villa with Pool and Jacuzzi

The Paradise - Ocean-Mountains-Jacuzzi-Air Con

Villa Acacia- Spectacular Ocean view & heated pool
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 $40 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 40 house 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 house rentals in Estreito da Calheta have air conditioning?
Absolutely! We offer over 40 house 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 50 villa 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 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 House Rentals in Estreito da Calheta?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 110 homes with free parking, over 120 homes with wifi, over 120 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
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- Rentals with pools Estreito da Calheta
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- Family-friendly rentals Estreito da Calheta
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- Praia do Porto do Seixal
- Monte Palace Tropical Garden
- Zona Velha
- Madeira Botanical Garden
- Praia da Calheta
- Ponta do Sol Beach
- Casino da Madeira
- Porto Moniz Natural Swimming Pools
- Praia Machico
- Complexo Balnear do Lido
- Praia de Garajau
- Cabo Girão
- Pico Do Areeiroo
- PR 11 - Vereda dos Balcões
- Casas Tipicas de Santana
- Fish Market
- Madeira Whale Museum
- Sé do Funchal
- Blandy's Wine Lodge
- Santa Catarina Park
- Ponta do Pargo
- Funchal Cable Car
- Cascata Dos Anjos
- Cristo Rei





