
Villa holiday rentals in Estreito da Calheta
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Top-rated villa rentals in Estreito da Calheta
Guests agree: These villas are highly rated for location, cleanliness and more.

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.

Casa Palheiro @ Casas Da Vereda [Thatched-Roof House]
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)!

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.

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.

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.

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.

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.

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!

Anjos Paradise Eden
It is a new and luxurious property with an outdoor private pool and surrounding garden with breath taking views of the Atlantic, within walking distance of the spectacular waterfall Cascata dos Anjos. The energy around you allows you to let your mind walk away from the worries of daily life and welcomes you to simply enjoy the moment, sorrounded by Nature and with the ocean at your feet.

Villa Gia: Your Home Away from Home
Villa Gia is a stylish retreat in Calheta with breathtaking ocean and mountain views. It features two en-suite bedrooms, an open-plan living area, full kitchen, Wi-Fi, and workspace—ideal for relaxation or remote work. Please note: Pool heating is an extra charge. Onsite parking may not suit low-profile or compact cars, but free on-street parking is available just outside the property.

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.

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 Estreito da Calheta villa rentals
Private villa rentals

House with sea view and heated saltwater pool

Isabel´s Villa - Funchal Seaside Villas

Myrtus - House with sea view and garden

Geo Calheta with Swimming Pool and Jacuzzi

Villa Sea - Rural Holiday Experience by SeaPearl

Sunset Villa with heated pool and a view

Blue Sea Tower, Private Heated Pool. Ocean view

Maison Du Soleil: swimming pool, sea view, mountain and village
Luxury villa rentals

Ohana Ocean View by LovelyStay

Villa Arco-Iris, a Home in Madeira

Luxury villa with infinity pool

The Bay House.:full ocean and Funchal bay view

Amazing villa FUNCHAL, panoramic sea view

Luxury Haven: Heated Pool, AC & Sun

Heated Pool • Gym • BBQ • Luxury • Outdoor Dining

Villa Amêndoa by LovelyStay
Villa rentals with a pool

Vila das Quebradas by An Island Apart

Luxury Villa Bianca by Holiday Rental Madeira

Lake House

* Villa with heated pool *

Valley View-Villa with heated pool and sauna

Villa Estrelícia by LovelyStay

Villa Canavial

Raposeira 22 - Villa with pool
Quick stats about villa rentals in Estreito da Calheta

Total holiday rentals
Explore 60 holiday rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta holiday rentals start at $106 AUD per night before taxes and fees

Verified guest reviews
Over 2,060 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Estreito da Calheta holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Estreito da Calheta rentals

4.9 Average rating
Estreito da Calheta stays are highly rated by guests—averaging 4.9 out of 5!
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