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Family-friendly holiday rentals in Calheta

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Calheta

  • Total holiday rentals

    Explore 250 holiday rentals in Calheta

  • Nightly prices starting at

    Calheta holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 8,560 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    250 of Calheta holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Calheta rentals

  • 4.8 Average rating

    Calheta stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Calheta

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Superhost
The image captures a wooden-roofed structure situated beside a calm sea, with expansive views of the coastline and towering rocky cliffs under a clear blue sky. The serene waters glisten in the sunlight, providing a striking contrast to the natural landscape.
Place to stay in Jardim do Mar
4.94 out of 5 average rating, 287 reviews

Uni WATER Studio

Wake up to absolute mind blowing scenery in this mezzanine featuring floor to ceiling high windows facing the island's stunning coastline, often requiring a second look to truly appreciate the beauty that this magnificent island has to offer. The mezzanine accommodates two people, has an ensuite bathroom, a fully equipped kitchen and also has access to its own private garden. Needless to say, our infinity pool is also there for you to enjoy and relax. Free parking is available in Jardim do Mar.

Top Guest favourite
A bright exterior space is shown with a round pool surrounded by a wooden deck. Sun loungers in green and umbrellas provide shaded areas. Colorful gardens with tropical plants encircle the house, which features large glass doors leading into an indoor living area.
Home in Arco da Calheta
4.98 out of 5 average rating, 203 reviews

Casa Sol e Vista

Moradia com boa vista e bom sol durante todo o dia. A casa está localizada num dos melhores locais da freguesia. Dispoe de dois quartos de dormir, sala / cozinha e duas casas de banho, com lotaçao para 6 pessoas. A casa esta situada no cimo de uma colina o que faz com que a casa tenha uma vista extraordinaria. No exterior tem um churrasco, um grande jardim e a piscina. Absoluta tranquilidade. Venha passar umas férias agradaveis na CASA SOL E VISTA. Contactar Duarte Paulo

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
4.96 out of 5 average rating, 456 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
Aerial view of the modern residence, showcasing its proximity to the coastline. The surrounding area features a mix of greenery and traditional homes, with the ocean visible in the background. The landscape highlights the tranquil setting by the sea, offering a serene environment.
Home in Jardim do Mar
4.97 out of 5 average rating, 115 reviews

CasaMar

Looking for a place to relax comfortably by the sea, or to continue your work online? This may be the place you're looking for. Enjoy your vacation in a modern house, located 100 meters from the beach in a quiet, sunny and warm area. As well as modern, it is very practical with a simple layout. It has a beautiful office, where you can complete your work in a quiet atmosphere, and with excellent internet connection. Perfect for those who intend to work and relax.

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, 182 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 two-story stone cottage features a traditional roof and vibrant red accents. A cozy outdoor seating area is seen in front, surrounded by a gravel courtyard. The structure is framed by scenic mountain views and has large windows allowing natural light to enter.
Home in Estreito da Calheta
4.88 out of 5 average rating, 191 reviews

Adega Do Avô 1 Amazing Seaview Trekking Beach

Adega do Avo is a set of 2 cottages fully equipped WITH AN INCREDIBLE SEA VIEW to give you the best experience. Cottage1 offered in this publication has a historical significance for the locality. With more than 100 years it has been totaly restored to offer the best comfort you deserve. We offer "Free car Parking in Premises" (Peace of mind). Its unbeatable location makes this set just 5 minutes from the best sandy beach of the island.

Top Guest favourite
An outdoor patio area features a wooden dining table accompanied by a comfortable hammock. Lush greenery frames the space, with ocean views visible in the background beneath a clear blue sky. The structural cover offers shade while maintaining a breezy atmosphere.
Apartment in Paul do Mar
4.99 out of 5 average rating, 245 reviews

Meu Pé de Cacau - Acerola Studio 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 handcrafted in basalt stone.

Guest favourite
An infinity pool offers panoramic ocean views, bordered by a well-maintained garden featuring blooming flowers and lush greenery. Sun loungers are positioned nearby for relaxation, while a shaded terrace area can be seen in the background, enhancing the tranquil ambiance.
Villa in Ponta do Sol
4.97 out of 5 average rating, 159 reviews

Villa Miradouro da Baleia by PAUSA Holiday Rentals

This magnificent, modern, private villa Miradouro da Baleia (Whale Watchtower) has some of the best ocean and mountains views on the island, with a infinity pool and located in a premium spot surrounded by spectacular cliffs, cropland, banana plantations and vineyards, it was carefully & tastefully restored/built in 2018 offering a unique experience of a Portuguese summer style accommodation!

Top Guest favourite
The image shows a spacious infinity pool extending towards the ocean, with lounge chairs positioned on the deck. The serene blue water reflects the sky, creating a seamless visual. A seating area is visible in the background, enhancing the outdoor space.
Apartment in Calheta
4.95 out of 5 average rating, 140 reviews

Marina View Apartment - Pool, Aircon & Ocean View

Welcome to Marina View Apartment! A fantastic 2 bedroom apartment set in a peaceful location of Calheta, the South Coast of the island where not only the sun shines almost every day but a fantastic location to explore the island. What truly makes this place special is the generous private outside space and infinity pool with spectacular views of the Atlantic ocean and Calheta Marina.

Guest favourite
A private heated swimming pool is set within a modern exterior. Clear blue water glistens under the sun, surrounded by sleek glass railing. Views of greenery and the distant sea can be seen beyond the pool, contributing to a serene outdoor environment.
Villa in Arco da Calheta
4.93 out of 5 average rating, 216 reviews

Stylish 3BR Villa with Heated Pool & Views

Modern 3-bedroom villa in sunny Arco da Calheta with sea & mountain views. Enjoy a private heated pool, BBQ terrace, fast Wi-Fi, and secure garage. Walk to restaurants and cafés, 10 minutes by car to Calheta Beach and 30 minutes to Funchal. Ideal for couples, families, or groups — the perfect base to explore Madeira.

Top Guest favourite
A sunny space features a splash pool surrounded by well-maintained grass and tropical plants. White walls contrast with dark volcanic rock in the background. A covered outdoor dining area is visible, providing a shaded space for meals while enjoying the outdoors.
Cottage in Arco da Calheta
4.98 out of 5 average rating, 212 reviews

Villa Papaya

An Outstanding Location, with a Fabulous View. Splash Pool and a Table to do meals outside. Unforgetable Sunset, with the sea and the Marina View! Villa Papaya Address: Rua Serra D’Água - Vereda do Morgadinho N. º 24 9370-076 Arco da Calheta

Guest favourite
A view from above showcases a sandy beach below, surrounded by a curved stone breakwater. Sunbathers and beach umbrellas dot the shoreline, while the blue ocean shimmers under the sunlight, reflecting the clear sky overhead.
Cottage in Calheta
4.96 out of 5 average rating, 125 reviews

Cliff House

Casa situada sobre a vila e a praia/mar da Calheta, ilha da Madeira. Possui dois quartos, duas casas de banho, sala, cozinha e BBQ. Possui ainda amplo terraço e acesso a áreas comuns; piscina, amplos jardins e miradouro privado.

Popular amenities for Calheta family-friendly rentals

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  5. Family-friendly rentals