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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 $91 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,160 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    150 of Calheta holiday rentals include wifi 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!

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
4.96 out of 5 average rating, 109 reviews

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).

Top guest favourite
Two lounge chairs in vibrant yellow and orange are positioned on a lush green lawn, offering a view of the ocean. Surrounding plants and trees enhance the tranquil garden setting, which features a partially fenced area for added privacy.
Villa in Fajã da Ovelha
4.98 out of 5 average rating, 163 reviews

Quinta São Lourenço – Casa Lagar | 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.

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, 288 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.

Guest favourite
A spacious terrace features a wooden pergola with flowing curtains, framing stunning sea views. A small round table accompanies two chairs, providing a perfect spot for relaxation. The vibrant blue sky enhances the tranquil ambiance, complemented by hints of nearby terracotta rooftops.
Flat in Arco da Calheta
4.96 out of 5 average rating, 207 reviews

Villa do Pombal 1 , Swimming pool,great sea views

The stunning apartment is located in one of the most sunny parts of Madeira .Villa to Pombal is a two floor building ,that contain two separate apartments. Each apartment have private entrance. It has breathtaking views , allows you to leave all stress behind and enjoy the natural beauty of Madeira. Excellent place to rest with easy access to many tourists attractions. Apartment is located 5 min. drive to sandy Calheta beach. 25 fountain walk begin is about 10min. drive from apartment.

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
4.97 out of 5 average rating, 459 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
An outdoor terrace features a private pool surrounded by lounge chairs with views of the surrounding landscape and ocean. A dining area with a table and six chairs is positioned on green grass, providing an inviting space for relaxation and gatherings.
Villa in Estreito da Calheta
4.98 out of 5 average rating, 52 reviews

King´s Paradise (Heated Pool and Sea View)

King´s Paradise is in a peaceful location, perfect for family-friendly holidays. It is the best choice for those that wish to experience a little of Madeira tradition, tranquillity and privacy, and easy access to the mountains. Ideally located for a lovely holiday surrounded by the beautiful Madeira countryside. Nearby: 5 minutes by car is the Vila da Calheta, with its man-made golden beaches, beautiful marina and a good choice of bars and restaurants.

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.
Flat in Paul do Mar
4.99 out of 5 average rating, 249 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 sit within the property, each with its own private outdoor area, alongside a shared infinity pool, social areas, and luxurious plantations hosting hundreds of different tropical fruits, planted on traditional agricultural terraces handcrafted in basalt stone.

Guest favourite
Villa in Calheta
4.97 out of 5 average rating, 29 reviews

Villa Nicuma by Escape to Madeira

Relax comfortably with incredible views of the Atlantic Ocean. This luxury villa is just a short walk from restaurants, bars, and the center of Villa da Calheta and its marina. The beach is nearby, and the house offers a rooftop pool overlooking the sea and marina, where you can enjoy water activities. Come enjoy an unforgettable vacation where the sea, sun, and comfort come together to offer you a unique experience.

Top guest favourite
An outdoor area presents a heated saltwater pool framed by vibrant green grass and blooming shrubs. A single lounge chair is positioned beside the pool, with the expansive ocean visible in the background under a clear blue sky. Sunlight reflects off the water's surface.
Flat in Jardim do Mar
4.98 out of 5 average rating, 153 reviews

☀️ 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.

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.
Flat in Calheta
4.95 out of 5 average rating, 141 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
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 Calheta
4.95 out of 5 average rating, 41 reviews

Luxury Villa Pérola

Welcome to our exquisite cliffside villa, with unparalleled ocean views. This opulent sanctuary is a dream at sunrise and sunset. Escape to this haven of natural beauty and luxury for an unforgettable retreat. A unique and tranquil getaway.

Popular amenities for Calheta rentals with a pool

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