Estreito da Calheta vacation rentals

4.86 out of 5 average rating, 159 reviews

An outdoor dining area features white tables and chairs under straw umbrellas, set against a backdrop of a rocky cliff. The space is well-lit and invites guests to enjoy meals in a relaxed atmosphere, with plants and decor adding to the inviting setting.

Condo in Caniço

Family friendly apartment swimming pool ocean view

A perfect family friendly apartment for who wants to spend a holiday with kids or friends in a wonderful island in Madeira which offers confortable climate all year long. Apartment is fully furnished and equipped with all the appliances that you need to spend your holidays. Amazing ocean view, perfect location to watch sunrise and sunset from the balcony. It is suitable for kids and infants, has high chairs from 0 to 5 years old, potty chair and a baby cot for the little ones, also a toy box.

4.92 out of 5 average rating, 64 reviews

Home in Arco da Calheta

Recanto das Florenças (1) - Great Views & Sunsets

This beautiful stone property, fully restored in 2019, sits in a peaceful rural location called Florenças, a small parish within Calheta, on the southwest region of the island, and has the most amazing panoramic ocean and mountains views. If you’re a nature lover and wish to get away from the noisy and stressful city life, Recanto das Florenças holiday houses offers you a great opportunity to relax and have a romantic or family holiday break, next to the mountains and the beach at the same time!

4.8 out of 5 average rating, 40 reviews

Home in Arco da Calheta

Cheerful 4 Bedroom Home

This spacious villa is the ideal location for an amazing holiday Here you can forget all your troubles in this serene place and the best sunsets Madeira can offer Free Wifi and parking is available This is not a shared house so the whole house is yours Seaviews from patio and balconies on every floor A short drive take you to the sandy beach of Calheta Levada walks are closeby or stay at home and enjoy a barbeque and entertainment the house offers which include pooltable, darts and table tennis.

4.87 out of 5 average rating, 104 reviews

A serene bedroom features a spacious bed adorned with decorative pillows, offering direct access to a balcony with expansive ocean views through open double doors. A lamp stands beside the bed, illuminating the cozy space.

Home in Paul do Mar

Hear the Ocean at Casa Beira Mar on the rocks

Forget your worries with the soundtrack of the sea at this comfy oceanfront home. From the front door experience the feel of a traditional old village, stepping onto a pedestrian alley which leads you to restaurants, bars & small harbour still used by fisherman from the village. From the back door find yourself directly at the seafront, with the sound of the waves hitting the rocks. Enjoy sweeping ocean views from two of the three serene bedrooms & relax with a drink on the sun soaked patio.

4.98 out of 5 average rating, 50 reviews

Home in Câmara de Lobos

Villa Belafonte

Feel at home in our breathtaking beachfront villa, offering stunning 360 views of this charming fisherman's village. Explore this traditional seaside village with its colourful fishing boats, cobbled streets, seaside promenade, swimming beach and much more. Located in the centre of the bay, where you can enjoy a lovely stroll on the promenade along the shoreline, go for a dip in the ocean or enjoy a sundowner at one of the nearby cafes whilst watching the traditional fisher boats in the bay.

A balcony view captures the expansive ocean and the skyline, framed by swaying palm trees and the rolling hills in the background. The glass railing provides an unobstructed perspective of the vibrant coastal landscape.

4.81 out of 5 average rating, 69 reviews

Levada dos Piornais, a Home in Madeira.

The apartment Levada dos Piornais is airy, bright and is ideal for two people. The apartment is 69 m2 and comprises one bedroom, a living room with dining table, kitchen, bathroom, a balcony with ocean view and a private parking. It is equipped with refrigerator, washer, hob, oven, microwave and other utensils, as well as bed linen, towels, Wi-Fi, Tv with international and children’s channels, and other amenities to provide a pleasant and relaxed stay. Location

Apartment in Madalena do Mar

A concrete pier extends into the blue sea, bordered by a rocky cliff on one side. Sunlight reflects off the water, and a few individuals can be seen socializing on the pier's edge. The landscape is characterized by vibrant earthy tones embedded in the cliff face.

4.88 out of 5 average rating, 8 reviews

Luz no Mar - New Roof

Escape to these charming beach houses, just steps from the ocean. Enjoy stunning sea views from the living room and a private deck perfect for morning coffee or evening sunsets. With a fully equipped kitchen, Wi-Fi, and easy access to local attractions, it's the perfect getaway for relaxation and adventure. As with most villas in Madeira, car hire is recommended. There is a public car park a few metres from the house where you can leave your car safely and free of charge.

4.89 out of 5 average rating, 44 reviews

An outdoor terrace showcases a smooth wooden deck with a dining set and chairs, framed by lush greenery and rocky landscaping. The view opens up to a distant landscape under a clear blue sky, enhancing the serene atmosphere of the location.

Home in Tabua

Mar a Vista by Your Madeira Rentals

Discover a remarkable rental retreat perched on a cliff, granting unparalleled sea and valley views. Ideal for two, this cozy haven offers a bedroom with high quality foam mattress, living room, and a fully equipped kitchen with a dining area. The bathroom invites relaxation, while the outdoor space captivates with an open-air shower, garden, and hammock. Embrace nature's allure in this tranquil and unique location, where every moment promises to be extraordinary.

An infinity pool reflects the sky and ocean, bordered by a white fence. Lush greenery and vibrant blooms are visible beyond the pool, while a palm tree stands to the right, enhancing the coastal scenery.

4.92 out of 5 average rating, 77 reviews

Superior Rentals - Beachfront penthouse (Lido)

Enjoy the perfect blend of oceanfront luxury, comfort, and prime location at this elegant two-bedroom penthouse in the heart of Funchal’s prestigious Lido Quarter — widely known as "The Hotel Zone". Surrounded by acclaimed beaches, fine restaurants, and vibrant nightlife, this exceptional location promises both relaxation and excitement. FREE PARKING INSIDE THE CONDO. We look forward to welcoming you to an exceptional stay on the beautiful island of Madeira!

4.96 out of 5 average rating, 113 reviews

The modern villa is set atop gently sloping terrain, with expansive windows and wooden accents. Surrounding greenery enhances the landscape, and a private turquoise pool can be seen below. A terrace with seating options is also visible, inviting relaxation amid the natural surroundings.

Cabin in Jardim do Mar

Woodlovers Jardim® (Heated Pool Optional) - Unit 1

Settled in a stunning organic green land, contemplating an amazing sea view, spectacular cliffs, surrounded by pieces of cropland, banana plantations and vineyards, we have found what today is WOODLOVERS. Combining this dream place with our engineering, sustainability, renewable energies and permaculture background, we were pioneers in the construction of the first contemporary 100% WoodHouse in Madeira Island respecting the nature and the natural environment.

Top guest favorite

A small balcony offers a view of the sea, framed by greenery and a decorative nature-inspired wall piece. A comfortable blue sofa is situated nearby, inviting relaxation while enjoying the surroundings.

4.98 out of 5 average rating, 135 reviews

SUPER Central - Deep Blue

Excelente localização / Great location Excelente vista / Great view PT: Elegante e confortável apartamento no coração do Funchal (Praça da Autonomia). Vista panorâmica para o mar e para a encosta do Funchal. Muito próximo de todas as comodidades e pontos de interesse. EN: Elegant and comfortable apartment in Funchal’s heart (Praça da Autonomia). Panoramic view of the sea and Funchal's hillside. Very close to all amenities and points of interest.

4.92 out of 5 average rating, 50 reviews

A spacious terrace is shown, featuring a swimming pool surrounded by tropical plants and lounge chairs. In the background, coastal hills meet the ocean under a clear blue sky, with traditional tiled rooftops visible.

Home in Lombo Do Doutor

Casa Nici magnificant sea views

Modern villa for rent in Calheta , in a quiet location, only 8 minutes walk to the beach of Calheta and shops, 30 minutes from Funchal and 40 minutes from the airport. It is ideally located for touring the island , with easy access to the North and its fabulous landscapes via Ribeira Brava. Porto Moniz and its natural swimming pools in the East are only 35 minutes away. Big game fishing and dolphin watching from the Calheta Marina.

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What guests are saying

Cardais Paradise View

5 out of 5 average rating, 11 reviews3 months ago

We had an amazing stay! House is brand new and located at the overlook of the Sao Vicente with the phenomenal views. Maria was very responsive and helpful. House is squeaky clean and contains everything you would possibly need. Absolutely the best stay- thank you so much for opening up your lovely home to us! We will be back!

Home in Sao Vicente

What guests are saying

Villa Pargo Sunsets

4.81 out of 5 average rating, 16 reviews2 months ago

Beautiful home with all the amenities that you need for a nice relaxing stay. The house is in an area where there are not a lot of shops nearby so be prepared with a car. The home is comfortable and well decorated. The views are amazing! Madeira is a beautiful treasure!

Home in Estreito da Calheta

What guests are saying

Sally's

4.94 out of 5 average rating, 16 reviews2 months ago

We just returned from a 10 day stay in this cozy townhouse up on the mountainside above Ponta do Sol, waking up to the beautiful sunrises in the morning. The house comfortably accommodated our group of 6 with plenty of space to gather together or find quiet corners for reading. Everything was comfortable, and the upstairs terrace became our favorite spot for morning coffee watching the sunrise. Fair warning: you absolutely need a car, and the steep, winding mountain roads require confidence behind the wheel. The location offered perfect isolation while being just 15 minutes from charming Ponta do Sol for restaurants and groceries. If you're seeking an authentic Madeiran experience with unparalleled views in a comfortable, stylish home, Sally's is the right place for you.

Home in Ponta do Sol

What guests are saying

Tropical Garden 1

4.94 out of 5 average rating, 16 reviews3 months ago

Fantastic place in a beautiful valley, with incredible view of the ocean, banana plantations and a beach nearby. Anibal is an amazing host, and the place is a gem. The garden with greens is only helping make this place even better. Thoroughly enjoyed the stay, the place, the host and the views! Thank you!

Home in Arco da Calheta

What guests are saying

Blue Dream Apartment

4.91 out of 5 average rating, 46 reviews1 week ago

We had a wonderful week in Madeira. Christian's apartment is spacious and clean. There is everything you need. It was pleasant to sleep. The only noise you can hear is the sound of the ocean. There is a small supermarket nearby and a good fish restaurant in the neighboring house. We were happy with our vacation. Thanks Christian!

Apartment in Paul do Mar

What guests are saying

Cantinho dos Ilhéus by ALMA Holiday Rentals

4.71 out of 5 average rating, 7 reviews6 months ago

Great stay. Place is awesome. Has everything you need and more. Lots of restaurants around but keep in mind, place is on top of the hill so it’s a bit of a climb every time you go to town/restaurants. Touristy city center is about 20 min walk but there is plenty restaurants/shops much closer.

Townhouse in Funchal

What guests are saying

Irlanda´s Villa - Funchal Seaside Villas

4.97 out of 5 average rating, 67 reviews5 days ago

Patrícia is a wonderful, caring, pro-active and supportive host. She is absolutely reliable and very passionate about her Villas. She made us feel welcoming and home. I highly recommend this place and would definitely go there again. Thank you, dear Patrícia – We loved it!!!

Villa in Funchal

What guests are saying

Villa, Dream View Ocean & Gardens, Cozy apartment

4.89 out of 5 average rating, 56 reviews2 weeks ago

The apartment was spotless and had good basic equipment. It is remote from shops and restaurants, but right next to the excellent bus route 29 that links the apartment to Funchal town centre, plus interesting places such as the Jardim Botanico, the cable car to Monte and two levada walks. Our only criticism was the local dogs barking a lot - but that wasn't Lino's fault! Lino was a great communicator (and his English is fluent) and he was most helpful on our arrival. He drove us from the airport and back, and also drove us into town on our first evening to stock up the fridge with food.

Guesthouse in Funchal

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Popular amenities for Estreito da Calheta vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Estreito da Calheta's top sights

Calheta Beach117 locals recommend

Mudas Museu Arte Contemporanea90 locals recommend

Joe's Bar37 locals recommend

Pukiki34 locals recommend

Sociedade dos Engenhos da Calheta31 locals recommend

Portinho27 locals recommend

Other great vacation rentals in Estreito da Calheta

4.89 out of 5 average rating, 18 reviews

A swimming pool reflects the vibrant hues of a sunset, creating a serene scene. The pool is surrounded by tiled flooring and a fence, offering panoramic views of the ocean and sky. The villa is partially visible in the corner, enhancing the tranquil atmosphere.

Home in Arco da Calheta

Magnificent villa with a heated pool

4.93 out of 5 average rating, 29 reviews

A round, multi-faceted mirror features a sunburst design, reflecting light and surroundings. It is positioned on a textured wall, adding depth to the space. Soft lighting can be seen in the background, contributing to a modern decor aesthetic.

Condo in Caniço

Rubeus

Apartment in Ponta do Sol

A bright sleeping area features a spacious bed covered with a blue throw. Flanking the bed are two nightstands, each with a modern lamp. A serene elephant artwork adorns the wall above the bed, complementing the room's light color palette.

5 out of 5 average rating, 6 reviews

Sunhouse B

An outdoor seating area features two yellow chairs and a glass table, set against a backdrop of a tranquil ocean view at sunset. The sky is painted with soft hues, and palm trees can be seen in the foreground, enhancing the serene atmosphere.

4.9 out of 5 average rating, 20 reviews

Suite BM |3 Pools-Gym-Park-Supermarket-Sea View-AC

4.88 out of 5 average rating, 17 reviews

A sunset view is captured over the lush hills of Madeira, with colorful skies blending orange and pink hues. Wooden outdoor seating is arranged on a stone patio, overlooking the vibrant landscape and terraced housing in the distance.

Apartment in Madeira

Private apartment with patio | Mountain & Sea View

4.92 out of 5 average rating, 71 reviews

A spacious terrace offers sweeping views of the surrounding mountains, bathed in soft sunlight. Two lounge chairs are positioned on the clean, bright floor, inviting relaxation while enjoying the serene natural landscape.

Home in Sao Vicente

Casa Verde Vale