Villa vacation rentals in Calheta

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Top-rated villa rentals in Calheta

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Guest favorite

An aerial view showcases a private infinity pool surrounded by a patio area. Lounge chairs and sun umbrellas are arranged on the terrace, bordered by vibrant greenery. The layout emphasizes the connection between outdoor relaxation spaces and the luxurious villa.

Villa in Funchal

5 out of 5 average rating, 5 reviews

Islander - Funchal Seaside Villas

Welcome to Islander, your luxurious retreat in Madeira boasting four bedrooms, each with an ensuite bathroom for utmost privacy and comfort. Step into the spacious living room and feel at home in our brand new thoughtfully designed villa. Islander features a terrace and garden area, inviting you to unwind amidst lush greenery and gentle sea breezes.Immerse yourself in the tranquility of your surroundings, or take a refreshing dip in the infinity pool that seemingly merges with the ocean horizon.

Guest favorite

A cozy outdoor dining area features a small wooden table set with breakfast items. Two checkered chairs offer a view of the large pool and the expansive ocean beyond, where gentle waves reflect the sunlight. The scene conveys a serene atmosphere, perfect for enjoying the surroundings.

Villa in Fajã da Ovelha

4.91 out of 5 average rating, 65 reviews

Secluded Sunset Villa on Cliff & 180° Ocean Views

Naturalis Villas, one of the best platforms for Madeira Villa Holidays Rental presents: Villa Miradouro is a secluded top of the cliff property with no direct neighbours, surrounded by extensive lush green gardens and a large 10 x 5 metre pool facing the ocean offering spectacular panoramic views and sunsets. Maid service is provided up to three days per week (subject to availability) to keep the property clean and spotless. The service includes cleaning, laundry, garden and pool maintenance.

Guest favorite

Villa in Estreito Calheta

4.89 out of 5 average rating, 45 reviews

Eco 1-bedroom 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)!

Superhost

A charming villa is framed by blooming bougainvillea and lush greenery, featuring an inviting infinity pool. Sunbeds are arranged poolside, ready for relaxation. Large windows reflect the sunlight, and the architecture combines traditional elements with modern comforts, offering a serene outdoor space.

Villa in Fajã da Ovelha

4.89 out of 5 average rating, 85 reviews

Blue Sea Villa. Private Heated Pool. Garden. Quiet

This CHARMING Villa commands an enviable location with stunning views over the Ocean. Newly renovated, traditional features combine with contemporary facilities, to offer luxury spacious accommodation. From a Palm Tree shaded entrance to Balconies for each room, the property exudes space to relax, breathe and to enjoy the serenity of this peaceful village. The Infinity Pool is the prime feature of the Villa. Bookings 7 nights, or 14 nights by request. Maximum occupancy 6 ADULTS and 2 Children

Guest favorite

A dining table is set on a covered veranda, surrounded by comfortable, padded chairs. The table is adorned with woven placemats, candles, and decorative items. In the background, views of the sea and lush greenery are visible, contributing to a relaxed outdoor atmosphere.

Villa in Estreito da CalhetaCalheta

4.93 out of 5 average rating, 42 reviews

Beautifully presented Villa in stunning location.

The Villa is in a quiet and peaceful location but has easy access to all local amenities, including supermarkets/shops , bars , restaurants, the Marina and Golden sand beach . A spacious , tastefully decorated villa , ideal for couples and families. Great combination of indoor /outdoor living - verandas and separate balcony with stunning sea views and mountain landscapes. I am new to Airbnb but see Trip Advisor 5 star reviews. Trip Advisor CERTIFICATE OF EXCELLENCE and Tourist Licence.

Guest favorite

Villa in Arco da Calheta

4.93 out of 5 average rating, 202 reviews

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

This stunning home completed in September 2016, features a heated pool & outside shower & BBQ area, plus hot & cold AC. The Villa is located in Arco da Calheta, a village in the south west & is within walking distance to mini-supermarkets, cafes, bars and pharmacy. Approx. 10 minutes drive to Calheta Beach, 30 minutes drive to Funchal and 45 minutes to the airport. Hillside Villa is ideal for couples, solo adventurers, families (with kids (cot & highchair provided), and big groups.

Guest favorite

A sparkling swimming pool features clear blue water, reflecting sunlight. Surrounding the pool, modern black lounge chairs are positioned for relaxation. The villa's glass doors open to the interior, complemented by potted plants and a vibrant hillside in the background.

Villa in Arco Da Calheta

5 out of 5 average rating, 12 reviews

" Blue Villa" swimming pool, Jaccuzi & Sauna

This fantastic 6 bedroom architect designed villa offers 5 star luxury private secluded accommodations for a wonderful holiday in the best residential area of Arco Da Calheta located at the end of a quiet peaceful Cul de Sac.This lovely villa provides garden furniture seating 9 people for alfresco living to relax drinking wine watching the sun as it sets over the sea after a day in the sun or hillwalking in the nearby mountains and levadas on the island.

Superhost

The villa's exterior is showcased at dusk, highlighting its stone facade and charming architecture. Outdoor seating is arranged on the lawn, surrounded by the garden's greenery. Warm light emanates from the windows, creating a welcoming atmosphere as the surrounding landscape is subtly illuminated.

Villa in Calheta

4.87 out of 5 average rating, 89 reviews

Villa Fedra - A hidden paradise

A charming two bedroom villa located on Sunny Calheta. Five minutes away from Madeira's best sandy beach. The villa has a big, beautiful garden ideal for outdoor dining & barbecues. Due to its location, and being a detached property with no immediate neighbours it provides a lot of privacy, peace and quiet. Villa Fedra provides an authentic Madeira living experience. Nature, sea views, and a peaceful living.

Guest favorite

The rooftop terrace features a rectangular swimming pool surrounded by a modern pool deck. Sunbeds and a sun umbrella offer relaxation space, while the gentle slope of the garden is visible in the background, enhancing the private outdoor experience.

Villa in Estreito da Calheta

5 out of 5 average rating, 7 reviews

Beautiful villa with rooftop pool CarmHim

This exquisite premium 2-bedroom villa, refurbished from the local grocery store, blends timeless charm with modern and premium comfort. With a rooftop swimming pool boasting breathtaking views of the sea and rolling countryside, this Cottage retains many of the original features. New to the market, special care has been taken to preserve the traditional architecture of memorHia carmHim villa.

Guest favorite

Villa in Ponta do Sol

4.98 out of 5 average rating, 126 reviews

Villa Miradouro da Baleia (Heated Pool optional)

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!

Guest favorite

Villa in Ponta do Sol

4.95 out of 5 average rating, 122 reviews

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.

Guest favorite

A contemporary villa is showcased from above, featuring expansive outdoor spaces and a private pool. Solar panels are visible on the roof. The surrounding area includes well-manicured greenery and seating arrangements, creating a seamless blend of comfort and modern design.

Villa in Funchal

4.83 out of 5 average rating, 6 reviews

Heated Pool • Gym • BBQ • PS5 • Outdoor Dining

An architectural gem in one of Funchal’s most prestigious areas. Villa Toscana offers sweeping views of the sea, mountains and bay. Contemporary design meets serenity across its 4 bedrooms, private heated pool, gym, cinema room and 360º rooftop. Designed for those who seek comfort, calm and exclusivity — curated by Madeira Dream Stays.