
Vacation rentals with a pool in Estreito da Calheta
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Estreito da Calheta

Total vacation rentals
Explore 150 vacation rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta vacation rentals start at G$6,270 GYD per night before taxes and fees

Verified guest reviews
Over 4,120 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

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

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

4.8 Average rating
Estreito da Calheta stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Estreito da 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.)

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.

Grey Rock Villa
The Grey Rock Villa proposes 2 en-suite bedrooms for up to 4 guests, and great facilities such as its private heated infinity swimming pool, designer fireplace and kitchen islet and other luxurious pieces of equipment. It blends harmoniously in the cliffy landscape and with the neighbouring 1 bedroom Beige Rock Villa while offering large views over the Atlantic ocean. The Rock Villas can also be rented together: a peaceful and stylish getaway on the South West coast of the island of Madeira.

Villa Rada, by Pausa Holiday Rentals
This stylish two-level villa features three bedrooms, each with its own private bathroom, plus an additional guest WC. The open-plan interior offers a bright, welcoming atmosphere with air conditioning and contemporary design. Outside, enjoy a private pool, barbecue area, comfortable sun loungers, and an outdoor dining area, all set against stunning sea and mountain views. Located in a peaceful area of the island, it’s the perfect place to relax and experience Madeira in comfort and style.

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.

MG House
Um oásis no coração da Zona Oeste da Madeira orientado a sul e com um pôr do sol fantástico. Zona residencial calma e com bons acessos. A 5min da praia, comércio e restaurantes e com uma ótima localização para explorar a ilha. Uma casa moderna com piscina de água salgada e aquecida (mediante pagamento), boas áreas, churrasqueira, zona de solário, jardim com ervas aromáticas, ginásio e estacionamento. Toda a casa é climatizada e com uma cozinha equipada para celebrar ótimos momentos.

Papaia Yurt ~ EcoGlamping 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 Bar, and stunning views of the sea and waterfall. 💧🌿 More pictures and vibes: @cantodasfontes

Wonderful tranquil villa with pool|Casa Laranja
Escape to this beautiful villa, perfectly located in a peaceful setting overlooking green fields and with panoramic views of the ocean, within easy walking distance of facilities. Ideal for families, friends and couples, the villa offers an infinity pool and everything you need for an unforgettable stay in Madeira. This stylish villa is set across two floors the contemporary design offers comfort and relaxation in an informal setting.

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.

Bella Vista (Heated Pool & Private Parking)
Welcome to Bella Vista, a modern villa built with high standards, offering comfortable accommodation for up to 6 guests. Enjoy unique privacy and peacefulness in this stylish getaway that offers a private heated pool and extraordinary views of Arco da Calheta. Offering all amenities needed for a perfect holiday! Approximately 10 minutes drive to Calheta Beach & 45 minutes to the airport.

Casa da Cascata B&B | Levada Houses
Detached cottage at Casas da Levada agritourism, with breakfast provided on a self-catering basis. From an old wine cellar, where the farm tools were kept, "Casa da Cascata" was rebuilt, keeping its original stone layout, balancing the rustic and modern line. Facing the pool, it offers an exclusive view of the Atlantic Ocean and a unique sunset from the western most tip of Madeira Island.
Popular amenities for Estreito da Calheta rentals with a pool
House rentals with a pool

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Condo rentals with a pool

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Spectacular Ocean and Cliff views with Pool

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New dream luxury appartment in the Madeira Palace.
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Top View Calheta, villa with pool and jacuzzi

Pereira's Domus
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- Praia do Porto do Seixal
- Madeira Botanical Garden
- Monte Palace Tropical Garden
- Casino da Madeira
- Zona Velha
- Praia da Calheta
- Ponta do Sol Beach
- Praia Machico
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- Pico Do Areeiroo
- Cabo Girão
- PR 11 - Vereda dos Balcões
- Sé do Funchal
- Fish Market
- Ponta do Pargo
- Madeira Whale Museum
- Casas Tipicas de Santana
- Santa Catarina Park
- Cristo Rei
- Blandy's Wine Lodge
- Funchal Cable Car
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