
Holiday rentals with a pool in Estreito da Calheta
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Estreito da Calheta
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Villa Lara, sea views, heated Pool A/C
Villa Lara is a fabulous modern single story three bedroom villa in the sought after area of Arco da Calheta. Lovely ocean and mountains views, sun terraces with a large private heated salt water pool and space for outside dining. There is an open plan fully fitted kitchen with a dining table for formal dining, leading to a comfortable sitting area with television with sliding doors leading outside. Facilities include aircon, heating, WIFI and parking. Approx. 10 minutes to Calheta beach. Fabulous spacious, light and modern 3 bedroom villa thoughtfully designed to maximize sun exposure and privacy. Fully fitted kitchen with all the required equipment to make you feel like you're at home. Large master bedroom with luxurious en-suite bathroom. Hot and cold air conditioning throughout, large heated swimming pool with ample sun terraces and garden area for relaxing or for children to run around. Alojamento Local License Number: 114112/AL We are at your disposal to help or answer your questions. We're contactable at any time via our mobile or by email. We will do our very best so you have a wonderful stay! Villa Lara is located centrally in Arco da Calheta with access to local amenities including various supermarkets, cafes, bars, restaurants and a pharmacy. Approx 10 minutes drive from the Villa and you'll be at Calheta Beach where you can enjoy the golden sand, several restaurants and book whale and dolphin watching tours. Villa Lara is ideal for couples, solo adventurers, families (with kids (cot & highchair can be provided)), and big groups. Villa Lara is set in a peaceful location ideal for walking the levadas (unmissable walks in Calheta include Paul da Serra, Rabacal (to Risco Waterall & 25 Fontes), Levada Nova and the Prazeres to Paul do Mar walk) and is close to a bus route. The property is approximately 30 minutes drive to Funchal and 45 minutes from the airport. A car is recommended so you can explore the island at your convenience. If you wish to book a private transfer with our local partners, please contact us in advance (which will be cheaper than taking a taxi direct from the airport).

Quinta São Lourenço - Casa Palheiro | Sunset & Pool
Tourist tax included > no extra fees at arrival Free cancellation up to 5 days before your stay The « Quinta São Lourenço » is a traditional Madeiran property of 3 000 m² from the 19th century, renovated into independent houses. The Quinta is an ideal holiday destination and is well known for its dominant position on the Atlantic Ocean, its beautiful flower garden and its shared outdoor swimming pool. Let yourself be surprised by the majestic sunsets and take a break with the roar of the Ocean.

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.

Old Town Funchal Seafront villa Pool & garden
Beachfront design home featured in Conde Nast Traveller w private swimming pool & tropical garden in the Old Town of Funchal. Just 200m, 5min walk to the city center, beach & restaurants. Free street parking & fast internet. 2 bedroom villa w 2 bathrooms, living room & kitchen w unlimited sea views. Stylish interiors & lots of outside relaxing, sunbathing & dining space with BBQ. Tropical oasis in the city - feels like the countryside. Perfect base to explore Madeira´s hikes & beaches in style

Casa Palheiro @ Casas Da Vereda [Thatched-Roof House]
Relax in class at 250 meters high on the sunny South West coast of Madeira, enjoying sunset and ocean views from the heated pool! The Casas Da Vereda are ideally located in a quiet countryside area with nothing but nature between you and the ocean. At 30 minutes drive from Funchal, 5 minutes drive to rock beaches in seaside villages / sand beaches by the marina of Calheta / “levada” walks. Please note that one can rent any combination of Casa Palheiro (T0), Casa Rural (T1), and (Casa Eco T2)!

Mango House
House with superb sun exposure, peaceful and stunning views over the sea and the mountain. Has 2 bedrooms (one with a double bed and the other with two single beds easily convertible into a double bed), a complete bathroom. On the ground floor open space with kitchen / living and dining room and toilet. Furniture and careful decoration. Outside enjoy the garden and the pleasant dining space with incredible views of the sea. The barbecue, mini-pool and shower complete your well-being.

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

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

Stonelovers® (Heated Pool Optional) - Unit3
Settled in a stunning organic green land, contemplating an amazing sea view, spectacular cliffs, surrounded by pieces of cropland, banana plantations and vineyards, we have found what today is WOODLOVERS. Combining this dream place with our engineering, sustainability, renewable energies and permaculture background, we were pioneers in the construction of the first contemporary 100% WoodHouse in Madeira Island respecting the nature and the natural environment.

☀️ Bright & Spacious w/ Pool & Oceanside View :D
Modern studio in the sunny and serene coastal village of Jardim do Mar, south west of Madeira Island. Studio D features an open plan design with kitchenette, lounging area, TV (with Netflix), a cozy queen size bed, a spacious bathroom with washing machine and a private, south facing balcony with ocean and pool view (24° to 26° Celsius). Guests have full access to the garden and heated saltwater pool.

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.

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.
Popular amenities for Estreito da Calheta rentals with a pool
House rentals with a pool

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Condo rentals with a pool

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Quick stats about holiday rentals with a pool in Estreito da Calheta

Total holiday rentals
Explore 130 holiday rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta holiday rentals start at $57 AUD per night before taxes and fees

Verified guest reviews
Over 3,940 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
130 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!
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- Madeira Botanical Garden
- Praia do Porto do Seixal
- Monte Palace Tropical Garden
- Casino da Madeira
- Praia da Madalena do Mar
- Praia da Calheta
- Ponta do Sol Beach
- Clube de Golf Santo da Serra
- Zona Velha
- Pico dos Barcelos
- Praia Machico
- Complexo Balnear do Lido
- Sé do Funchal
- Cristo Rei
- Casas Tipicas de Santana
- Porto Moniz Natural Swimming Pools
- Fish Market
- PR 11 - Vereda dos Balcões
- Praia de Garajau
- Blandy's Wine Lodge
- CR7 Museum
- Santa Catarina Park
- Madeira Whale Museum
- Cabo Girão




