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

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.

Country House @ Casas Da Vereda
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)!

Old Wine Villa
Welcome to Paradise! Come stay at our cozy Villa with a splendid Atlantic ocean view by the infinity pool! This house was first built in 1932 and since then it has been know as "Casa do Vinho Velho", "The Old Wine House". My great-grand mother used to tell stories about the old man "Vinho Velho" and his passion for his wine and agriculture. The house has been updated but we have kept old features, like an old brick oven in the kitchen and 3 stone rocks for vine hanging in the living room!

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

Endless Blue House
Endless Blue is a traditional stone house, with modern improvements. It has a panoramic view over the Atlantic Ocean. It stands in a popular location for people who like to spend time in a quiet and peaceful place. It offers a suite, with a very beautiful sea view. The property also has outdoor leisure areas with excellent sun exposure throughout the day. It benefits from a large salt water swimming pool (10mX4m), where you can enjoy a spectacular sunset.

Woodlovers Jardim® (Heated Pool Optional) - Unit 1
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.

Meu Pé de Cacau - Mango Studio in Paúl do Mar
Meu Pé de Cacau is a tropical fruit garden and island retreat 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.

☀️ 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.

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.

STONE HOUSE
Esta casa é a simbiose entre o passado tradicional das gentes e da ilha e a reconstrução actual e versátil. Acomoda 4 pessoas. Situada sobre a praia e a vila, goza de tranquilidade e bons acessos a "Levadas", "veredas" e à Floresta Laurissilva.
Popular amenities for Calheta rentals with a pool
House rentals with a pool

Vincents Place | Ocean View | Swimming pool

Casa Velha D. Fernando

Casa da Cascata B&B | Levada Houses

Sales House

Kombi Studio(private pool) by STAY Madeira Island

Casa do Lado

Typical house above the sea

Calheta Tangerine House
Condo rentals with a pool

Ocean View Apartment in Madeira

Spectacular Ocean and Cliff views with Pool

COSY STUDIO AT LIDO WITH POOL

Casa Mar Azul 3

Luxury Big Apartment/Ocean view/Free Parking

Sunny Ocean View Apartment • Pool & Open Horizon

Monumental Apartment

Ocean view and Infinity pool Apartment
Other vacation rentals with a pool

Jade Tree Studio at Casa da Vila

Tropical Honeymoon Suite

Cottage Palha, hanging in a tropical garden

Peak A Boo (Private Heated Pool & Private Parking)

Top View Calheta

Villa Acacia- Spectacular Ocean view & heated pool

Socalco Nature Calheta - Hall House

Casa Nenufar
Quick stats about vacation rentals with a pool in Calheta

Total vacation rentals
Explore 150 vacation rentals in Calheta

Nightly prices starting at
Calheta vacation rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 5,960 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
150 of Calheta vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Calheta rentals

4.9 Average rating
Calheta stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Funchal Vacation rentals
- Madeira Island Vacation rentals
- La Palma Vacation rentals
- Santa Cruz de Tenerife Vacation rentals
- Porto Santo Vacation rentals
- Ponta do Sol Vacation rentals
- Machico Vacation rentals
- Santa Cruz de La Palma Vacation rentals
- Anaga Vacation rentals
- São Vicente Vacation rentals
- Arco da Calheta Vacation rentals
- Ribeira Brava Vacation rentals
- Beachfront rentals Calheta
- House rentals Calheta
- Rentals with outdoor seating Calheta
- Pet-friendly rentals Calheta
- Waterfront rentals Calheta
- Rentals with beach access Calheta
- Smoking-friendly rentals Calheta
- Apartment rentals Calheta
- Rentals with a patio Calheta
- Rentals with a hot tub Calheta
- Rentals with a fire pit Calheta
- Rentals with a fireplace Calheta
- Family-friendly rentals Calheta
- Villa rentals Calheta
- Rentals with a washer and dryer Calheta
- Rentals with pools Madeira
- Rentals with pools Portugal
- Cristo Rei
- Madeira Botanical Garden
- Praia do Porto do Seixal
- Casino da Madeira
- Monte Palace Tropical Garden
- Praia da Calheta
- Pico dos Barcelos
- Praia da Madalena do Mar
- Ponta do Sol Beach
- Clube de Golf Santo da Serra
- Complexo Balnear do Lido
- Zona Velha
- Sé do Funchal
- PR 11 - Vereda dos Balcões
- Blandy's Wine Lodge
- Santa Catarina Park
- Cascata Dos Anjos
- Praia Machico
- Casas Tipicas de Santana
- Pico Do Areeiroo
- Madeira Whale Museum
- Praia de Garajau
- Ponta de São Lourenço
- CR7 Museum




