
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 140 vacation rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

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Over 4,200 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
140 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).

Vila Aguarelas with pool by Stay Madeira Island
A unique stay in an elegant and refined accommodation, modern and comfortable, thoughtfully designed just for you! Vila Aguarelas offers 3 suites, each featuring a double bed and private bathroom. In an open-plan layout, there’s a living room with a dining table and a fully equipped kitchen. You can also enjoy the incredible pool (optional heating upon request; additional cost of €35 per night, minimum stay required—please notify at the time of booking or at least one week prior to arrival).

Casa do Terrāço - Quinta Falcões Do Sol
Casa Terrãço is a restored stone house that combines the unique charm of a centuries-old structure with modern comfort. The house features an open floor plan on the first level with a fully equipped kitchen and living space that offers ocean views through a big glass door. The top floor contains a spacious bedroom that opens to a large private terrace, providing breathtaking views of the ocean. Outside you will have a private area with a fire pit and access to the shared heated saltwater pool.

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.

Casa Palheiro @ Casas Da Vereda
Relax in class at 250 meters high on the sunny South West coast of Madeira, enjoying sunset and ocean views from the heated pool! The Casas Da Vereda are ideally located in a quiet countryside area with nothing but nature between you and the ocean. At 30 minutes drive from Funchal, 5 minutes drive to rock beaches in seaside villages / sand beaches by the marina of Calheta / “levada” walks. Please note that one can rent any combination of Casa Palheiro (T0), Casa Rural (T1), and (Casa Eco T2)!

Stunning 3BR Villa | Ocean-View, Private Pool
Atlantic View by Costa Living – a peaceful and spacious ocean-view villa in Arco da Calheta. This freshly renovated and newly furnished 3-bedroom home (sleeps 9) features a private pool, panoramic Atlantic and mountain views, balcony, and modern open-plan living. Enjoy fast Wi-Fi, Smart TV, fully equipped kitchen, laundry and private garage. Set among nature and hiking trails, just minutes from Calheta Beach, Madalena do Mar Beach, and cafés. Perfect for families and friends. Car required.

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.

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

Villa Bisa Atlantic View ,heated pool
A 2 bedroom villa located in Arco da Calheta. the property has 2 modern style bedrooms, 2 and a half luxurious modern bathrooms,outdoor shower ,new modern kitchen, living room, etc... The property has just been renovated,modern decorated with high quality furniture which is extremely comfortable. The villa also includes cable ,Satellite TV and internet. The property on the outside has BBQ ,pool with a panoramic Seaview ,a nice eating area.

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

Eco Fajã Villas - Deluxe - 60m above sea level
High above the coastline is a private sanctuary where luxury meets nature. With sweeping panoramic sea views, a larger heated infinity pool, and an expansive garden, this villa is designed for those who seek space, tranquility, and exclusivity. Its sleek open-plan interiors, flooded with natural light, blend seamlessly with the outdoors, creating an effortless flow between modern comfort and Madeira’s breathtaking landscape.

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

Villa Vera Garajau - Madeira Island

Relax Over The Sea -12391/AL

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Villa Panorama - Luxury Villa with Jacuzzi-Calheta

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Casa Mar Azul 3

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- Praia do Porto do Seixal
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