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Beachfront vacation rentals in Estreito da Calheta

Find and book unique beachfront homes on Airbnb

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Popular amenities for Estreito da Calheta beachfront rentals

Pet-friendly beachfront home rentals

Superhost
The image captures the exterior view of Casa da Janela, showcasing its single-story structure in a tranquil setting. The surrounding area features lush greenery and a distant mountain backdrop, with the sun casting a warm glow on the property. A car is visible parked in front.
Home in Ponta Delgada
4.83 out of 5 average rating, 106 reviews

Casa da Janela - Wood

CoringeRating, 5 stars1 month ago
Great house, even better garden! We had a very pleasant stay.
Guest favorite
A contemporary building with large windows captures views of the ocean and surrounding landscape. The structure is surrounded by well-maintained gardens and cultivated grapevines, while a pathway of stone leads towards the entrance, providing access to the scenic outdoor areas.
Farm stay in Lombo Do Doutor
4.96 out of 5 average rating, 27 reviews

Socalco Nature Calheta - Apothecary's House

MaartenRating, 5 stars9 months ago
Excellent stay. Good location as a base. The restaurant is very tasty and offers an added value to the accommodation. A beautiful location with an eye for detail.
Top guest favorite
Apartment in São Martinho
4.98 out of 5 average rating, 125 reviews

Casa da Betty - luxurious w/aircondition

Isak IziRating, 5 stars1 month ago
It has been sometime since I stayed in a real home-y and cosy house like Betty's. Our whole group (two families with small children ) was very pleasantly surprised by this beautifully decorated home. There were many essentials as well as some offerings by the host readily available. The location(although not very close to the historic center) is fantastic as it is possible to walk to some famous rock pools and a beach, as well as many restaurants, a mall and a supermarket. Would recommend to anyone in a heartbeat.
Guest favorite
A bright bedroom features a spacious bed adorned with a neutral-colored blanket. A laptop sits on the bed, and a sliding glass door opens to a private balcony with two wooden chairs and a table, offering views of the surrounding hills and city.
Apartment in Funchal
4.9 out of 5 average rating, 128 reviews

Patio da Achada View Apartment

JackieRating, 5 stars1 month ago
Raquel’s place was absolutely impeccable. After five nights of hopping between different beds, my friend and I felt so lucky to land here for three restful nights — exactly what we needed. The space had everything we could have asked for and more. The check-in process was super easy, and Raquel had everything clearly laid out with thoughtful instructions. Thank you for sharing your beautiful home with us — it truly felt like a breath of fresh air.
Guest favorite
A scenic pathway leads towards the ocean, lined with vibrant wisteria flowers in shades of purple. Lush greenery complements the vibrant blooms, while the calm sea is visible in the background, enhancing the coastal ambiance of the setting.
Home in Sao Vicente
4.92 out of 5 average rating, 118 reviews

Pebble Beach House- Casa da Fajã

Huey YuinRating, 5 stars4 days ago
Beautiful house. The driveway is easy to miss if you're not paying close attention the first time. Well equipped kitchen. Next to a walking trail by the sea. Well situated to drive to other attractions around the island. Fanal forest, P Moniz, Santana, PR16, were not far away.
Top guest favorite
An aerial view captures a modern infinity pool surrounded by a sun deck, overlooking vibrant rooftops and the ocean beyond. Lush greenery and lounge chairs enhance the space, while the bustling streets of Funchal and distant hills create a picturesque backdrop.
Apartment in Funchal
5 out of 5 average rating, 51 reviews

Terrace, Grill & Infinity Pool @ Savoy Insular

NoahRating, 5 stars1 week ago
This is a beautiful Airbnb and we truly enjoyed our stay — from beginning to end. The accommodation was next-level… beautiful interior and private deck on the second floor, and a shared infinity pool that overlooked the busy street below, but felt like you were in your own little paradise. Definitely recommend and will stay here again on our next trip to Madeira!
Guest favorite
A wooden dining table and folding chairs are arranged on a stone patio, offering views of the Atlantic Ocean. A lone tree leans towards the sea, complementing the natural landscape of rocky shorelines and green hills under a clear blue sky.
Cottage in Casas Próximas
4.88 out of 5 average rating, 248 reviews

Casa da Praia

AnoukRating, 5 stars1 month ago
Amazing location in picturesque village
Guest favorite
The image features a bright yellow house surrounded by palm trees and blooming foliage. A staircase leads to the entrance, which is illuminated by natural light. The upper balcony can be seen with decorative railing, enhancing the overall welcoming appearance of the property.
Home in Jardim do Mar / Calheta / Madeira
4.94 out of 5 average rating, 135 reviews

Sofia's Place

ClaireRating, 5 stars1 week ago
Family home, nice in a very nice quiet village without a car. We fell in love with Jardim do Mar, its small alleys with its typical gardens! Thank you Sofia, we felt at home 😊🙏

Beachfront home rentals with a pool

Guest favorite
An infinity salt-water pool is framed by vibrant green foliage and colorful flowering plants. The clear water reflects the surrounding landscape, providing a calming retreat. The pool area is positioned adjacent to a modern building featuring clean lines and a spacious terrace.
Guest suite in Ponta do Sol
4.94 out of 5 average rating, 102 reviews

A View For You 2

QuentinRating, 5 stars2 weeks ago
Perfect apartment with an amazing view. The location is very well located for discovering the island. Terrace, pool as in the photos, no surprises. Short apartment to book without a second thought
Guest favorite
A serene outdoor pool area is surrounded by lush tropical plants and palm trees. Loungers are positioned beside the pool, with white umbrellas providing shade. The clear blue water reflects the sunlight, inviting relaxation in a tranquil setting.
Home in Arco da Calheta
4.97 out of 5 average rating, 29 reviews

Casa Estrelicia

Tomi-JussiRating, 5 stars1 month ago
The apartment was clean and upscale. The surroundings are peaceful, even if other apartments have residents. The yard and garden are beautiful with details. The retreat-like quiet vibe and views of the atlantic were charming. The owners are friendly and helpful.
Guest favorite
Cottage in Calheta
4.95 out of 5 average rating, 73 reviews

VIEWPOINT HOUSE

JosiahRating, 5 stars1 month ago
This place was amazing! The house took a little bit to get to, some stairs and pathways, but once there, the view was breath taking, the accommodations amazing, and the host excellent. João met us to help us navigate down the first time, and was super accommodating and helpful. Calheta was a great location for us as a base to see the rest of the island and the beach and waterfront was really nice to walk along. I would highly recommend staying here on your trip.
Guest favorite
A modern stone house features large glass windows that provide views of the surroundings. The patio area is designed with natural stone flooring, and the roof extends over columns, offering shaded outdoor space. A tranquil sunset sky adds a touch of warmth to the scene.
Cottage in Madeira
4.96 out of 5 average rating, 47 reviews

Rochão Village by Rent2U - 2 Bedrooms (Élvio)

LeoniRating, 5 stars2 weeks ago
Beautiful accommodation in a fantastic location – ideal for those who like hiking! The apartment was very clean and quiet, check-in was straightforward, and the host responded quickly to messages. Absolutely recommended!
Superhost
A spacious living area features a large window with a view of the outdoor scenery. A comfortable sectional sofa with patterned cushions complements a modern coffee table. A television is positioned on a sleek white cabinet, enhancing the contemporary design of the space.
Apartment in São Martinho
4.95 out of 5 average rating, 19 reviews

Stunning Sea View-Supermarket-AC-Park-3 Pools-Gym

SteveRating, 5 stars1 month ago
wonderful stay. clean and tidy
Guest favorite
A swimming pool is viewed under a bright sky, reflecting shades of blue. Surrounding lounge chairs are positioned on the pool deck, while a table and chairs provide space for outdoor dining. Scenic landscapes are visible in the background.
Home in Corujeira
4.89 out of 5 average rating, 102 reviews

Villa Golden Charm

DavidRating, 5 stars1 month ago
We really enjoyed the accommodation! (family of 6 people) This one is well located, a beautiful view, very peaceful and private place. It is very well equipped, heated pool (for €30/day), barbecue available, very spacious and clean. Which makes it a great value. We recommend it!
Guest favorite
A two-story villa set against a mountain backdrop, showcasing a clear blue pool surrounded by sun loungers. The exterior features a blend of local stone and modern design elements, with large windows offering views of the surrounding landscape and waterway.
Villa in Paul do Mar
4.96 out of 5 average rating, 49 reviews

Villa Sea - Rural Holiday Experience by SeaPearl

PatriciaRating, 5 stars2 months ago
We had a fantastic time on the island. In addition to the nature that makes Madeira so fascinating, we were also able to spend some very relaxing days in our accommodation. Everything was just like in the pictures, so we could start our vacation with a great feeling. The accommodation was modern, clean and very luxurious with a pool and the number of rooms, each with its own bathroom. And who wouldn't want to wake up with a view of the sea? Wonderful. Henrique was also easy to contact if we had any questions and check-in with the key box was very simple. There is a small supermarket in this small town if you need anything. Otherwise, Calheta is not far away with larger shopping facilities. There are a few restaurants within walking distance of the accommodation, although the accommodation with its large kitchen and outdoor grill is of course also perfect for a meal. Thank you for a wonderful time in Madeira, we'd love to come back!
Superhost
A sunlit swimming pool surrounded by palm trees and tropical plants reflects the sky above. Sun loungers are positioned beside the pool, with an umbrella providing shade. The ocean is visible in the background, creating a serene coastal ambiance.
Villa in Arco Da Calheta
4.78 out of 5 average rating, 23 reviews

Secluded Villa In Tropical Garden | Villa Mar I

BeatrijsRating, 5 stars1 month ago
Breathtaking. Wherever you looked, every view was beautiful. We enjoyed every minute in the house and around the house. Inside and outside is luxurious and equipped with every comfort. The garden is beautiful and the pool very large and beautiful. We could not believe our eyes on arrival, while of course we had already seen the photos, we couldn't believe our eyes, it was so paradise. We would love to come back.

Private beachfront home rentals

Guest favorite
An outdoor terrace features comfortable seating with a coffee table, surrounded by greenery. A partial ocean view is visible, along with the distant rooftops. The structure is shaded by a wooden pergola, enhancing the space for relaxation or leisure.
Apartment in Ponta do Sol
4.96 out of 5 average rating, 81 reviews

Sun Balconies - Ponta do Sol

AudreyRating, 5 stars1 month ago
The place was great. The view from the beautiful terrace! Nuno is an extremely kind host. He responds quickly and gave us plenty of recommendations. The departure and arrival at the accommodation was made very simple and pleasant thanks to him. In addition, Ponta do sol is a very convenient place: a supermarket with gas station just down the village, great restaurants and the beach being a beautiful place to see the sunset. I can only recommend this place to stay in Madeira. It's been a real favorite!
Superhost
A hot tub is illuminated in soft blue light, surrounded by lush greenery. The calming water contrasts with the twinkling lights of the coastal town in the distance, all set against a night sky. A few palm-like plants add natural beauty to the scene.
Cottage in Arco Da Calheta
4.94 out of 5 average rating, 88 reviews

Casa do Pico

PhilippeRating, 5 stars2 weeks ago
We had a wonderful stay at Celina’s home. The view from the balcony was stunning, especially at night and we felt right now home. The hot tub and bath tub were a bonus as well. One thing to note is that there was a tourist fee of €16 which we don’t believe was in the description. Would definitely recommend if you’re looking for a quieter place to stay.
Top guest favorite
A lounge chair is situated on a grassy area, with a clear view of the ocean in the background. Glass barriers provide an unobstructed sightline to the sea, framed by clouds and a blue sky. A palm tree adds a touch of greenery to the scene.
Home in Estreito da Calheta
5 out of 5 average rating, 48 reviews

Villa Pinheira II panoramic sea view very private

AlgirdasRating, 5 stars2 weeks ago
good place, good communication, everything is great, I recommend
Guest favorite
A sunlit bedroom featuring a spacious bed dressed in neutral bedding, with natural light streaming through large windows. An inviting seating area is located in the corner, and scenic views of the ocean are visible through the window, framed by soft curtains.
Apartment in Ponta do Sol
4.98 out of 5 average rating, 40 reviews

Freitas Paradise, a Home in Madeira

SandraRating, 5 stars1 month ago
The three of us spent a week here. The view is amazing. You can quickly get to the hiking trails, supermarket and restaurants, but you can also cook and barbecue yourself and enjoy the holiday on the balcony overlooking the sea.
Top guest favorite
An outdoor dining area features a wooden table set for four, complemented by glasses and dinnerware. A panoramic view of the sea and mountains is displayed in the background, with sunny skies and scattered clouds enhancing the scenery.
Home in Campanário
4.95 out of 5 average rating, 37 reviews

BoaVista-2Bed Cosy panoramic Sea & Mountain View’s

BethanyRating, 5 stars2 weeks ago
A very beautiful place! plenty of room for our family of 4. Thank you!
Guest favorite
A well-equipped kitchen features wooden cabinetry and a countertop with a sink overlooking the ocean. Natural light floods the space through a large window, highlighting essentials such as a kettle, coffee maker, and drying rack.
Apartment in Seixal
5 out of 5 average rating, 35 reviews

SUPER Seixal Beach - T0

LinaRating, 5 stars2 weeks ago
Carlo‘s place has been very clean & matched the description perfectly. Seixal has been an amazing location for us - absolutely pictorial, dramatic and local. It was as we expected and better, thank you so much!
Guest favorite
An outdoor terrace is featured with a wooden dining table and comfortable seating. Woven chairs surround the table, which is set with a bowl of fruit, pastries, and drinks. The ocean view is unobstructed, with the sun shining bright overhead.
Home in Câmara de Lobos
4.96 out of 5 average rating, 46 reviews

Casa da Rocha

MilesRating, 5 stars3 months ago
Absolutely loved our stay here for the week! We loved the ability to walk into town and grab food at any time. We found a number of great restaurants! We also loved being within the energy of the town of Camara De Lobos. It was very warm, welcoming, and vibrant. We loved the home and felt it was clean, beautiful, and the perfect opportunity to slow down life and enjoy the sound of the ocean. The breeze was able to keep us cool (mid February visit for us), the sound of the ocean helped us drift off peacefully, and we enjoyed the opportunity to lounge in the sun on the many decks available. Parking was simple and free right around the house. We had very prompt communication and felt very supported. Overall the location was a great spot to adventure to the rest of the island. If we ever return to Madeira this is where we will be staying!
Top guest favorite
A dining table is set for four, overlooking a serene ocean view. Glassware and dinnerware are arranged neatly, while a jacuzzi is visible in the foreground. The sunset creates a warm ambiance, enhancing the overall tranquil setting.
Hut in Tábua
5 out of 5 average rating, 87 reviews

Glamping Maracujá: Oasis Paradise

Fabian EwaldRating, 5 stars1 week ago
We really enjoyed our stay. It is a beautiful place and we can recommend it!

Quick stats about beachfront rentals in Estreito da Calheta

  • Total rentals

    40 properties

  • Nightly prices starting at

    R360 ZAR before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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