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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 $118 NZD 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, 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

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).

FamilyLocationHospitality

4.95 out of 5 average rating, 114 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

Casa Sol e Vista 2 is located in one of the best locations in the parish, next to house no. 1. It has 2 bedrooms, a living room/kitchen and 3 bathrooms, accommodating 6 people. The house is located on top of a hill, which gives the house an extraordinary view. Outside, there is a barbecue, a large garden and a swimming pool. Absolute tranquility. Come spend a few pleasant days at Casa Sol e Vista 2. Contact Duarte Paulo

LocationValueAccess

4.98 out of 5 average rating, 103 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 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.

LocationValuePool

4.99 out of 5 average rating, 225 reviews
Guest favourite
An infinity pool offers panoramic ocean views, bordered by a well-maintained garden featuring blooming flowers and lush greenery. Sun loungers are positioned nearby for relaxation, while a shaded terrace area can be seen in the background, enhancing the tranquil ambiance.
Villa in Ponta do Sol

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!

LocationFamilyParking

4.97 out of 5 average rating, 161 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.

ValueLocationIndoor spaces

4.95 out of 5 average rating, 144 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

A&M House II, the perfect place to enjoy your best vacation on Madeira Island. Located in a quiet area with a mild climate, it offers guests all the comfort they need to feel at home. Its stunning views make every evening unforgettable with its stunning sunsets. Come discover Madeira and enjoy the comfort that A&M House II has to offer.

FamilyValueBiking

5.0 out of 5 average rating, 51 reviews
Guest favourite
A private heated swimming pool is set within a modern exterior. Clear blue water glistens under the sun, surrounded by sleek glass railing. Views of greenery and the distant sea can be seen beyond the pool, contributing to a serene outdoor environment.
Villa in Arco da Calheta

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.

LocationFamilySolo travel

4.93 out of 5 average rating, 220 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

This house is the symbiosis between the traditional past of the people and the island and the current and versatile reconstruction. It sleeps 4 people. Situated on the beach and village, it enjoys tranquility and good access to "Levadas", "veredas" and the Laurissilva Forest.

LocationValueHospitality

4.94 out of 5 average rating, 116 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.

FamilyValueNearby

4.85 out of 5 average rating, 168 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

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.

FamilyLocationWi-Fi

4.95 out of 5 average rating, 43 reviews
Guest favourite
Villa in Arco da Calheta

Casa Diana Pool and Sea views

Casa Diana - a spacious modern cottage in the peaceful village of Loreto. A large sun terrace with swimming pool and amazing views over the Atlantic ocean offers a great place to relax and enjoy the sun.

LocationFamilyCleanliness

4.89 out of 5 average rating, 181 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

Fully renovated house, where you can spend a fantastic, restful vacation. It has all the comfort to make you feel at home, and you can enjoy a beautiful swimming pool with a privileged view of the sea!

FamilyValueBathroom

4.94 out of 5 average rating, 201 reviews

Popular amenities for Calheta rentals with a pool