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Villa holiday rentals in Calheta

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Top-rated villa rentals in Calheta

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Superhost
An outdoor area features a private pool surrounded by lounge chairs, all overlooking expansive sea views. A shaded dining area is positioned nearby, creating an inviting space for relaxation. Lush greenery lines the perimeter, enhancing the serene atmosphere.
Villa
4.78 out of 5 average rating, 120 reviews

Quinta Falcoes - A villa with an amazing view

Quinta Falcoes has some of the most amazing views on the island. With a 180 panoramic view of the sea, you can also watch the end of the island lighthouse at night and the falcons hunting by day in the ravine. Quinta Falcoes is a modern and well equipped villa with a private pool, outdoor eating and seating areas, large bbq and a playroom with table tennis table, book & dvd library and a cinema area. The house is perfect for groups of walkers, couples who want to relax and larger family groups.

Guest favourite
A spacious bed is centered in the room, adorned with decorative pillows and a colorful blanket. Nightstands are positioned on either side, each featuring soft lighting. A decorative straw hat and a bright flower are placed on the bed, enhancing the serene atmosphere.
Villa
4.94 out of 5 average rating, 159 reviews

Country House @ 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)!

Guest favourite
A shaded outdoor seating area features two comfortable chairs facing a panoramic view of the Atlantic Ocean. Lush green plants frame the scene, enhancing the serene environment. A small table is placed between the chairs, complementing the peaceful setting.
Villa
4.95 out of 5 average rating, 75 reviews

Beige Rock Villa

The Beige Rock Villa proposes one bedroom, for up to 2 guests, and a large living room opening to a comfortable outdoor area, including a private heated infinity swimming pool. Its stylish design blends harmoniously in the cliffy landscape and with the neighbouring 2 bedrooms Grey 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.

Superhost
An inviting outdoor area features a heated swimming pool reflecting the sunset over the sea. Glass railings provide unobstructed views, while a stone feature complements the serene environment. The surrounding area is equipped with stylish tiles and ample space for relaxation.
Villa
4.86 out of 5 average rating, 100 reviews

Fajã Refuge

The property has 3 bedrooms, one in a suite (all with air conditioning), 2 toilets, OpenSpace living room and kitchen, barbecue, laundry room, heated outdoor pool (extra charge), sports field, pool table, outdoor relaxation space and a garage for 4 cars. The house has a security system and is equipped with all the appliances necessary for your comfort. You'll also be able to enjoy a wide and unobstructed sea view, amazing Sunsets, and unmatched silence.

Guest favourite
An outdoor dining area is set up under a wooden gazebo, featuring a large table surrounded by metal chairs. A picturesque view of the ocean and cliffs is visible in the background, illuminated by the warm glow of sunset. The space includes decorative lights strung overhead.
Villa
4.92 out of 5 average rating, 172 reviews

Madeira Black Sand House by Stay Madeira Island

Stay Madeira Island presents Madeira Black Sand Beach House! Set on the north coast of Seixal beach, Madeira Black Sand Beach House offers a dream view towards the black sand and the deep blue sea surrounded by green cliffs. This century old stone house has been with the same family for 30 years and was used as a weekend second home. The owners decided to share this unique spot with the world and the refurbished plan had the guest's comfort in mind.

Guest favourite
A dining area is presented on a spacious terrace, featuring a round table set with plates and utensils. A colorful umbrella provides shade, while potted plants decorate the space. The ocean view is visible beyond a glass railing, complemented by a statue positioned on the terrace.
Villa
4.95 out of 5 average rating, 170 reviews

Panoramic Oceanview Penthouse

Penthouse with Stunning Sea View, Large Terrace & Private Elevator Access. Perched peacefully on a cliffside, this elegant penthouse offers the perfect blend of comfort and breathtaking views. Step out onto the spacious terrace and take in the panoramic view of the sea- ideal for morning coffee, sunset drinks or enjoying a relaxing BBQ . The only sound your can hear, are the ocean waves and some birds. Area, including veranda, 170 m2.

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
5 out of 5 average rating, 52 reviews

Villa with large pool and fantastic view

NEW :-) Swim your laps in the long pool. Enjoy the view of the Atlantic Ocean and lush nature while sitting in the garden. A very stylish place that is located in a small quiet village. To relax - but also to be active. Jogging, hiking and swimming - all possible right by the house. Restaurants can be reached in a few minutes by car. For work, there is a study and fast internet. End the day with a glass of rosé and the sunset.

Top 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
4.93 out of 5 average rating, 214 reviews

Heated pool, hot & cold AC, BBQ, views & parking

Modern 3-bedroom villa in Arco da Calheta with stunning sea & mountain views. Features a private heated pool, BBQ area, fully equipped kitchen, fast Wi-Fi, and secure garage. Walk to a handful of restaurants, cafés & pharmacy. Just 10 mins to Calheta Beach, 30 mins to Funchal. Ideal for couples, families (cot & highchair provided), or groups. Close to top Levada walks. Comfortable, spacious, and perfect for exploring Madeira.

Top guest favourite
A balcony offers a sweeping view of the sea and Paul do Mar, with a wrought iron railing framing the scene. The sunlight casts a warm glow over the landscape, creating a serene atmosphere. Lush greenery surrounds the area, enhancing the natural beauty.
Villa
4.98 out of 5 average rating, 191 reviews

Quinta São Lourenço≈≈≈ Casa Palheiro ≈≈≈

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.

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
4.97 out of 5 average rating, 149 reviews

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!

Top guest favourite
A private pool is set against a backdrop of lush greenery and a rustic yellow house with a tiled roof. The pool’s clear blue water is visible, complemented by the surrounding plant life that adds to the serene atmosphere.
Villa
4.98 out of 5 average rating, 146 reviews

Quinta do Alto

Situated inside an old farmhouse of the island, and located on the outskirts of the capital Funchal, near the Botanical Garden, the villa is a one bedroom with one double bed, a toilet, common room and kitchenette. Outside the villa, guests have an exclusive use of the swimming pool, encased in a rich flora and varied fruit growing. Relax in this unique and tranquil spot.

Top guest favourite
An aerial view captures a spacious outdoor terrace with patterned tiles. Two lounge chairs are positioned under a straw umbrella, next to a wooden dining table set for several guests. Surrounding greenery adds a touch of nature to the relaxing space.
Villa
5 out of 5 average rating, 124 reviews

Casa 112

Enjoy a elegante experience in this central and unique space, full of glamour and minimalism. Very close to the sea, two to three minutes walk in a quite and relax environment. You are super welcome to enjoy this little peace of heaven.

Popular amenities for villa rentals in Calheta

Quick stats about villa rentals in Calheta

  • Total holiday rentals

    Explore 40 holiday rentals in Calheta

  • Nightly prices starting at

    Calheta holiday rentals start at £74 per night before taxes and fees

  • Verified guest reviews

    Over 1,700 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 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!

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