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Holiday rentals with a pool in Calheta

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Calheta

  • Total holiday rentals

    Explore 150 holiday rentals in Calheta

  • Nightly prices starting at

    Calheta holiday rentals start at $98 AUD per night before taxes and fees

  • Verified guest reviews

    Over 6,520 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

    150 of Calheta holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Calheta rentals

  • 4.9 Average rating

    Calheta stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Calheta

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A large heated saltwater pool is set against a backdrop of ocean and mountain views, framed by modern glass doors. Sunlight reflects off the water, enhancing the tranquil atmosphere. Spacious terraces surrounding the pool provide ample space for relaxation.
Villa in Arco da Calheta

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).

4.94 out of 5 average rating, 116 reviews
Top Guest favourite
A bright and airy living area features large glass doors that open to an ocean view, allowing natural light to fill the space. A cozy blue sofa is positioned near a small dining table and chairs. Beyond the doors, a glimpse of the garden and pool can be seen.
Apartment in Jardim do Mar

☀️ 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. New Tourism Tax already included in the price, so we'll take care of that for you.

4.98 out of 5 average rating, 162 reviews
Guest favourite
An outdoor dining area features a wooden table set with dishes and plants, surrounded by a few chairs. The rustic orange exterior of the adjacent building complements the lush greenery. The sea view can be seen in the background under an overcast sky.
Home in Arco da Calheta

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.

4.93 out of 5 average rating, 119 reviews
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

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

4.97 out of 5 average rating, 472 reviews
Top Guest favourite
A modern house with a vibrant red roof is positioned on a hillside, overlooking the ocean and surrounding landscape. The outdoor area includes a swimming pool and a spacious terrace, offering expansive views of both the coastline and lush greenery.
Villa in Arco da Calheta

CASA SOL E VISTA 2

A Casa Sol e Vista 2 está localizada num dos melhores locais da freguesia, a par da casa nr 1. dispoe de 2 quartos de dormir, sala / cozinha e 3 casas de banho, com lotaçao para 6 pessoas. A casa esta situada no cimo de uma colina o que faz que a casa tenha uma vista extraordinaria. No exterior tem um churrasco, um grande jardim e a piscina. Absoluta tranquilidade. Venha passar uns dias agradaveis na Casa Sol e Vista 2. Contactar Duarte Paulo

4.98 out of 5 average rating, 105 reviews
Top Guest favourite
An infinity pool stretches over a wooden deck, with views of the expansive Atlantic Ocean and dramatic cliffs. Sunlight reflects off the water's surface, enhancing the serene atmosphere. Surrounding greenery complements the natural setting, inviting relaxation and contemplation.
Apartment in Paul do Mar

Meu Pé de Cacau - Studio Papaia 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.

4.99 out of 5 average rating, 225 reviews
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 Arco da Calheta

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.

4.95 out of 5 average rating, 144 reviews
Top Guest favourite
An infinity pool stretches across the scene, seamlessly merging with the horizon of the ocean. Surrounding greenery adds a touch of nature. Sun loungers are positioned on a terrace, offering a peaceful space for relaxation, with stunning views visible in all directions.
Home in Arco da Calheta

Villa Pérola | Pool & Panoramic Ocean View

Experience Madeira at Villa Pérola, an elegant villa in Arco da Calheta with a private pool and panoramic Atlantic views. With 3 bedrooms, modern interiors and spacious outdoor areas, it’s the perfect place to relax, enjoy spectacular sunsets and spend an unforgettable holiday by the sea.

4.95 out of 5 average rating, 44 reviews
Guest favourite
A tranquil scene captures the reflection of vibrant greenery in a serene pond. Surrounding the water, various tropical plants and flowers provide a lush backdrop to the recently restored house, characterized by its stone structure and warm red exterior. Sunshine enhances the inviting atmosphere.
Home in Estreito da Calheta

Casa do Penique ORGANIC

Casa do Penique Organic can be found on a dead end road, in a quiet Madeiran village, only 400 minutes from Funchal. It has been carefully restorated and now offers a spacious and relaxing space where you can enjoy an ocean view while sitting by the pond.

4.85 out of 5 average rating, 172 reviews
Top Guest favourite
A charming stone house features a warm exterior with a pink trim. Wooden chairs are positioned near the entrance, while a staircase leads to the upper level. The surrounding area includes a garden that adds to the natural setting.
Home in Arco da Calheta

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.

4.94 out of 5 average rating, 116 reviews
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

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

4.98 out of 5 average rating, 219 reviews
Guest favourite
The image displays a serene swimming pool reflecting the vibrant colors of the sky at sunset. A wooden deck surrounds the pool, with lounge chairs positioned for relaxation. The landscape features lush greenery in the background, enhancing the tranquil ambiance.
Home in Arco da Calheta

Casa Cro | Ocean View

Casa totalmente recuperada, onde poderá passar umas fantásticas férias descansado. Possui todo o conforto para que se sinta em casa, podendo usufruir de uma bela piscina com vista privilegiada para o mar!

4.94 out of 5 average rating, 203 reviews

Popular amenities for Calheta rentals with a pool

KitchenWi-FiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top Guest favourite
The image captures a view of Casa Nambebe, with a terracotta roof and surrounded by lush banana trees. An inviting infinity pool reflects the blue ocean, while the rugged coastline and greenery enhance the tranquil setting. The house is positioned on a hillside overlooking the sea.
Home in Ponta do Sol

Typical house above the sea

4.99 out of 5 average rating, 200 reviews
Top Guest favourite
An outdoor dining area is displayed, featuring a table set with orange cloth and breakfast items including fruits and pastries. Behind the table, chairs are arranged neatly. A hammock is visible in the backdrop, with a panoramic view of the ocean and hills beyond.
Home in Arco da Calheta

Villa Bisa Atlantic View ,heated pool

4.97 out of 5 average rating, 159 reviews
Top Guest favourite
An infinity pool reflects the vibrant hues of a sunset over the ocean. The surrounding terrace features minimalistic railings, emphasizing unobstructed views of the coastal landscape and the sky's dramatic colors.
Home in Arco da Calheta

Moradia Syso

4.95 out of 5 average rating, 132 reviews
Guest favourite
A modern villa is showcased with clean architectural lines and large glass windows, surrounded by a manicured lawn featuring palm trees. An outdoor dining table and chairs are arranged on a patio adjacent to the heated infinity pool, overlooking scenic views of the landscape.
Home in Arco da Calheta

Panoramic View: Lux 3 bed w/ heated pool

4.97 out of 5 average rating, 113 reviews
Guest favourite
A stone exterior of the house is shown, featuring red trim that contrasts against the grey walls. A small bistro table with two chairs is positioned on the stone patio. Lush green grass and flower beds, along with a railing, overlook a vast view of the Atlantic Ocean under a clear blue sky.
Home in Arco da Calheta

Endless Blue House

4.97 out of 5 average rating, 115 reviews
Guest favourite
A spacious infinity pool overlooks the coastline and ocean, surrounded by sun loungers and palm trees. The house features large glass doors that provide stunning views of the surrounding landscape. The tranquil setting highlights the connection between the property and its natural surroundings.
Home in Ponta do Sol

Relax Over The Sea -12391/AL

4.98 out of 5 average rating, 103 reviews
Top Guest favourite
An expansive view of the Atlantic Ocean is presented from the edge of a private infinity pool. The tranquil waters reflect the clear blue sky above, while rolling hills and the coastline of Camara de Lobos are visible in the background.
Home in Câmara de Lobos

Peak A Boo (Private Heated Pool & Private Parking)

5.0 out of 5 average rating, 101 reviews
Top Guest favourite
An outdoor seating area is highlighted by a decorative pillow featuring a floral design, resting against a woven chair. In the background, the infinity pool overlooks the expansive blue Atlantic ocean, framed by a clear sky.
Home in Tabua

Old Wine Villa

4.95 out of 5 average rating, 150 reviews

Condo rentals with a pool

Guest favourite
A light-filled living area is furnished with a gray sofa adorned with decorative pillows. A coffee table with storage sits in front, while a floor lamp provides soft lighting. Large glass doors open to a backdrop of hills and greenery, enhancing the inviting space.
Condo in Campanario

Tropical Sunset D

4.96 out of 5 average rating, 101 reviews
Superhost
A dining table is set with breakfast items, including a pitcher of juice and plates with fruit and pastries. The sea view stretches out beyond the balcony rail, revealing cliffs and coastal buildings under a clear sky.
Condo in Funchal

Spectacular Ocean and Cliff views with Pool

4.85 out of 5 average rating, 126 reviews
Guest favourite
A serene view captures the sun setting over the sea, reflecting golden hues on the water's surface. Pine trees frame the image, highlighting the tranquil pool located below. The gentle curve of the balcony adds depth to the peaceful ambiance.
Condo in Funchal

Sunset Paradise, Funchal: sounds of the sea

4.94 out of 5 average rating, 103 reviews
Top Guest favourite
A spacious terrace features a glass railing with views of the ocean and surrounding landscape. Lush greenery is visible below, along with a pool area. Mountains frame the horizon, adding depth to the serene coastal scenery.
Condo in Funchal

New dream luxury appartment in the Madeira Palace.

4.99 out of 5 average rating, 146 reviews
Superhost
A modern living area features a large sectional sofa adorned with cushions and a soft throw. Natural light floods in through wide windows, presenting a view of the surrounding landscape. A minimalist entertainment unit and dining area are also visible, enhancing the open feel of the space.
Condo in Funchal

Renala II "With Pool" by PAUSA Holiday Rentals

4.95 out of 5 average rating, 103 reviews
Guest favourite
Condo in Funchal

Monumental Apartment

4.86 out of 5 average rating, 173 reviews
Guest favourite
Condo in Funchal

Apartamento Varandas do Funchal

4.86 out of 5 average rating, 152 reviews
Guest favourite
A swimming pool is situated on the roof, featuring clear blue water under a bright sky. A rail surrounds the pool, offering unobstructed views of the sea and surrounding landscape.
Condo in Funchal

Charming Lido Flat I

4.93 out of 5 average rating, 147 reviews

Other holiday rentals with a pool

Top Guest favourite
A spacious dining area is highlighted by a round wooden table surrounded by stylish chairs. Floor-to-ceiling glass walls offer panoramic views of the Atlantic Ocean. A modern kitchen is partially visible, and a unique light fixture hangs above the table, providing ambient illumination.
Villa in Estreito da Calheta

Grey Rock Villa

4.96 out of 5 average rating, 77 reviews
Guest favourite
Villa in Arco da Calheta

Villa Arco-Iris, a Home in Madeira

4.95 out of 5 average rating, 22 reviews
Guest favourite
Villa in Estreito da Calheta

Sunny Ocean View Villa - Calma

4.96 out of 5 average rating, 23 reviews
Top Guest favourite
A modern bedroom is presented with large glass doors that offer expansive sea and mountain views. A spacious bed is dressed with white linens, complemented by a decorative throw and a rolled towel. A pink accent chair adds a pop of color to the neutral decor.
Villa in Estreito da Calheta

King´s View (Heated Pool and Sea View)

4.93 out of 5 average rating, 54 reviews
Superhost
Villa in Arco da Calheta

Villa Nicuma by Escape to Madeira

4.94 out of 5 average rating, 34 reviews
Guest favourite
A private heated pool reflects the serene colors of the sunset, set against a backdrop of the ocean. A wooden deck surrounds the pool, complemented by glass railings for an unobstructed view of the landscape.
Home in Arco da Calheta

A&M House II

5.0 out of 5 average rating, 51 reviews
Top Guest favourite
Two outdoor chairs with plush cushions face a long pool, offering a view of the Atlantic Ocean and the surrounding greenery. A small wooden table sits between the chairs, enhancing the inviting outdoor space.
Villa in Arco da Calheta

Villa mit großem Pool und fantastischem Blick

5.0 out of 5 average rating, 66 reviews
Top Guest favourite
An outdoor pool is showcased, featuring a clear blue surface reflecting the sky. Two lounge chairs are positioned beside the pool area, surrounded by green foliage and a barrier offering a view of the ocean. A bright blue pool cover is visible nearby.
Condo in Arco da Calheta

Casa Mar Azul 3

5.0 out of 5 average rating, 72 reviews

Destinations to explore