
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.

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).

Villa Palheiros - A Magnificent Ocean View
Perfect home to enjoy the nature and beauty the island of Madeira has to offer. This villa has a stunning ocean view, situated in a very quiet rural area, where you can enjoy a magnificent climate in a swimming pool with endless views. This villa was built and designed to offer the best comfort to its guests. Perfect housing for families, where you can also find all the necessary amenities in a maximum of 5 minutes by car. The air conditioner is a extra service (contact the owner for more info.)

Panoramic View: Lux 3 bed w/ heated pool
Stunning modern villa with a private, heated infinity pool, 3 bedrooms and bathrooms, enjoying sea & mountain views. Located in one of the most sought-after areas with the best weather in the South West of Madeira island, the villa is unique in that it has a dedicated entertainment floor. Situated 5 mins away from Calheta Beach with its excellent restaurants on the marina & the same distance from Madalena do Mar beach. The house enjoys sun on the pool area from late morning until sunset.

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

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.

Uni AIR Studio
Uni AIR is our top floor studio with a balcony that directly overlooks the horizon and the island's shore. Decorated with a bohemian feel, with a bamboo arch holding a dreamcatcher above the bed, this studio has a double bed,a fully equipped kitchen and an ensuite bathroom ensuring all the privacy and tranquility one is seeking. Feel like being on top of it all? Follow the steps up to Uni AIR's private terrace and let yourself enjoy the surroundings.

☀️ 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. Note: AC available after July 1st.

Meu Pé de Cacau - Studio Mango 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.

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!

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.

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

Villa Serenity

Luxury Ocean View Villa | Pool I Calheta I Madeira

Casa da Lombada

Villa Ocean Wave Calheta, Oversized Pool

Villa Panorama - Luxury Villa with Jacuzzi-Calheta

Casa do Lado

Old Wine Villa

STONE HOUSE
Condo rentals with a pool

Apartamento Ocean View Madeira

Spectacular Ocean and Cliff views with Pool

Casa Mar Azul 3

Luxury Big Apartment/Ocean view/Free Parking

III - Savoy Monumentalis, By Pausa Holiday Rentals

Sunny Ocean View Apartment • Pool & Open Horizon

Monumental Apartment

Whitehouse408 Sw.Pool & Pvt. Parking
Other vacation rentals with a pool

Villa Céu e Mar

Casa da Venda

Villa Sea - Rural Holiday Experience by SeaPearl

The Sunset Avenue w/infinity pool(optional heated)

Casa Joaquim by Rent2u, Lda

Botanica Living | Acacia Apt

Beachfront Villa w Pool & Rooftop Old Town Funchal

Villa Gia: Your Home Away from Home
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 ﺩ.ﺇ 257 per night before taxes and fees

Verified guest reviews
Over 6,160 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
50 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!
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- Praia do Porto do Seixal
- Madeira Botanical Garden
- Monte Palace Tropical Garden
- Casino da Madeira
- Ponta do Sol Beach
- Zona Velha
- Praia da Calheta
- Porto Moniz Natural Swimming Pools
- Praia Machico
- Complexo Balnear do Lido
- Cabo Girão
- Blandy's Wine Lodge
- PR 11 - Vereda dos Balcões
- Fish Market
- Ponta do Pargo
- Praia de Garajau
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- Sé do Funchal
- Funchal Cable Car
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