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Villa holiday rentals in Calheta

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Top-rated villa rentals in Calheta

Guests agree: these villas are highly rated for location, cleanliness and more.

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Superhost
The image features a charming stone structure with an orange, sloped roof, reflected in the tranquil waters of a heated pool. Colorful stained glass elements adorn the entrance, complemented by planters and a palm tree nearby, all set against a serene blue sky.
Villa
4.95 out of 5 average rating, 217 reviews

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)!

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 mit großem Pool und fantastischem Blick

NEU :-)Ziehe Deine Bahnen im langen Pool. Geniesse beim Sitzen im Garten den Blick auf den Atlantik und die üppige Natur. Eine sehr stilvolle Unterkunft, die sich in einem kleinen ruhigen Dorf befindet. Zum Entspannen -aber auch um Aktiv zu sein. Joggen, Wandern und Schwimmen - alles direkt am Haus möglich. Restaurants sind mit dem Auto in wenigen Minuten erreichbar. Zum Arbeiten gibt es ein Arbeitszimmer und schnelles Internet. Beschließe den Tag mit einem Glas Rosé und dem Sonnenuntergang.

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

Refúgio da Fajã

A propriedade dispõe de 3 quartos, um deles em suíte (todos com ar condicionado), 2 WC's, sala e cozinha OpenSpace, churrasqueira, lavandaria, piscina exterior aquecida (custo extra), campo de desportos, mesa de bilhar, espaço de relaxamento exterior e garagem para 4 carros. A casa dispõe de sistema de segurança e é equipada com todos os eletrodomésticos necessários para o seu conforto. Poderá também desfrutar de uma ampla e desafogada vista mar, incríveis Sunsets e um silêncio inigualável.

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.

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, 171 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
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 modern kitchen area features sleek cabinetry with wooden countertops and steel appliances. Large glass doors provide a view of the terrace and ocean beyond, while a wooden dining table with several chairs is positioned nearby. Natural light fills the space, highlighting the neutral color palette.
Villa
4.99 out of 5 average rating, 69 reviews

CasadaOvelha 2, modern & spacious villa in Calheta

Our new house is located in one of the sunniest and warmest corners of the south-west coast of Madeira. The new Casa da Ovelha 2 is surrounded by banana trees with a dramatic view mixed of mountains and sea. ​Just above the marina of Calheta, the location of our brand new holiday home is very quiet and yet so close to everything you need to spend an amazing time. Perfect for holidays or remote working!

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, 148 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, 145 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.

Superhost
A well-maintained garden is visible, featuring neatly trimmed grass and colorful flower beds. In the background, rolling hills and greenery can be seen beneath a clear blue sky, creating a serene outdoor atmosphere. A stone pathway leads toward the house.
Villa
4.88 out of 5 average rating, 103 reviews

Conceição House country area

With a stunning sunset, Conceição House provides two bedrooms (plus a small/single one), two bathrooms, living room, kitchen, garage, and plenty of outdoor space with garden and sun areas. The area is calm and peaceful, with sea and mountain views. Rocha Vermelha PR 28, Levada Nova, 25 Fontes PR 6, Rabaçal, Risco PR 6.1, are some Levadas you can do from the house.

Guest favourite
An outdoor terrace is shown with a dining table set for six, surrounded by wicker chairs. An umbrella provides shade over the table, while the ocean is visible in the background. Sunlight illuminates the tiled flooring and surrounding greenery.
Villa
4.92 out of 5 average rating, 132 reviews

Une vue à couper le souffle (Wi fi)

Passionnés de Madère,nous avons voulu trouver et faire partager un coin de paradis au cœur de cette île fantastique.Nous espérons que cette maison ravira les hôtes comme elle nous a enchantés avec son emplacement et sa vue exceptionnelle !

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 € 85 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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