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Villa vacation rentals in Estreito da Calheta

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Popular amenities for Estreito da Calheta villa rentals

Private villa rentals

Guest favorite
The exterior view showcases a modern two-story structure with a contrasting orange-tiled roof. A spacious balcony equipped with outdoor furniture overlooks the surrounding landscape. A well-maintained garden borders the property, adding a touch of greenery to the inviting entrance.
Villa in Arco da Calheta
4.88 out of 5 average rating, 16 reviews

Paradise views - Pereira House

LisaRating, 5 stars3 weeks ago
We had a very nice stay! The place was clean, well appointed and exactly as described. The location is quiet and ideal for relaxing. The contact with the host was friendly and straightforward. A small note: A dishwasher would be a helpful addition, and the drain in the bathroom should possibly be checked, as there were occasional problems there. Otherwise everything was wonderful – we would love to come again!
Guest favorite
A serene outdoor area features modern lounge chairs arranged near a private pool. The expansive view showcases the ocean under a clear blue sky, with lush greenery surrounding the space. The inviting design encourages relaxation and enjoyment of the beautiful tropical surroundings.
Villa in Arco da Calheta
5 out of 5 average rating, 19 reviews

Ohana Ocean View by LovelyStay

JulietteRating, 5 stars1 week ago
We absolutely loved our stay in Madeira! The property was incredibly clean—honestly one of the cleanest places we've ever stayed. Everything was spotless and so well maintained. The welcome gifts were such a thoughtful touch—local produce that gave us a warm introduction to the island. The house had everything we needed, from great coffee to handy extras like Tupperware, which made day trips really convenient. The sunsets from the property were absolutely stunning—something we looked forward to every evening. The location was great for accessing shops and restaurants nearby, but we’d definitely recommend having a car to explore more of the island comfortably. All in all, a fantastic stay. We’d return in a heartbeat!
Superhost
An outdoor area features a swimming pool surrounded by several lounge chairs with umbrellas. Lush hillside scenery and homes are visible in the background, providing a serene backdrop to the relaxing space.
Villa in Arco da Calheta
4.9 out of 5 average rating, 71 reviews

SUNNYSIDE VILLA

CathyRating, 5 stars3 weeks ago
We had a great time at Carmina's Villa. Everything was perfect. The house has all the features necessary for the success of our family vacation. The pool is a real asset. Thanks to Carmina for the breakfast on arrival.
Superhost
An expansive coastal view captures the charming village nestled between lush green hills and the Atlantic Ocean. The coastline is dotted with colorful houses, and the vibrant hues of the sea contrast against the clear blue sky with wispy white clouds.
Villa in Paul do Mar
4.8 out of 5 average rating, 45 reviews

New! OCEAN PARADISE Beach Villa 100M from beach

JulieRating, 5 stars1 month ago
Large house ideal for a family, beautiful kitchen, terrace and sea view. Iva is a welcoming host who takes the time to leave us lots of information to discover this beautiful island. So we were able to discover the dolphins at a preferential and zn price passing through a local agency😊... The accommodation is located in the southwest of the island, in a small quiet fishing village, and where you can easily park your rental car and when you know the parking difficulties on the island, it is not negligible. The rental car is necessary, but the village allows access to the whole island by beautiful roads and we particularly appreciated the calm and sweetness of living when we returned from our sports days, where we met a lot of people. Small supermarket, bakery, restaurants, small typical cafes, so many little extras that made our stay super pleasant. great value for money... we recommend it ++
Guest favorite
A suspended orange and white hammock is positioned on a wooden terrace, offering sweeping views of the sea and surrounding landscape. Clear skies and sunlight enhance the tranquil atmosphere, inviting relaxation in this serene outdoor space.
Villa in Estreito da CalhetaCalheta
4.93 out of 5 average rating, 44 reviews

Beautifully presented Villa in stunning location.

LucyRating, 5 stars1 week ago
Within seconds of arriving I was swinging on Ian's hammock looking at the ocean - it was bliss! The apartment is extremely spacious, it has everything you need for a comfortable stay. The views are spectacular. The kitchen is really well appointed with everything you need if cooking 'at home' is something you like to do. I would stay again! Thank you Ian!
Guest favorite
A private pool is framed by lush green plants, with clear blue water reflecting the sky. The surrounding patio features sunbathing areas, offering views of the Atlantic Ocean in the background under a bright blue sky.
Villa in Madalena do Mar
4.77 out of 5 average rating, 75 reviews

"Miradouro" over the Atlantic with private pool

JoseRating, 5 stars2 weeks ago
We spent four wonderful nights in Madalena do Mar and the experience couldn't have been better. The village is charming, quiet and perfect for disconnecting, with stunning sea views and sunsets that look like they were taken from a postcard. The accommodation exceeded our expectations: clean, comfortable and with all the details well thought out to make you feel at home. We loved waking up every morning to the sound of the sea in the background and enjoying breakfast on the terrace overlooking the banana plantations and the Atlantic. The location is ideal for exploring the island: close to Calheta, Ponta do Sol and other points of interest, but far enough away from the hustle and bustle to enjoy peace and nature. In addition, the locals were incredibly friendly and hospitable. You can feel the warmth of the people of Madeira. All in all, it was a perfect getaway. We would recommend this area (and this accommodation) without hesitation, and we look forward to coming back soon.
Top guest favorite
A serene balcony setting features a glass-top table with two woven chairs, offering a panoramic view of the coastline under a colorful sky at dusk. The horizon showcases subtle hues of orange and purple as the landscape lights begin to twinkle.
Villa in Santa Cruz
4.97 out of 5 average rating, 76 reviews

Sunrise Bay Balcony

ChangwenRating, 5 stars2 days ago
We really enjoyed our stay at Rui's beautiful home! We were in awe of the view the moment we arrived. The house was in pristine condition and looked exactly as in the pictures. Our family of 5 was very comfortable. Rui also left lots of goodies for us, which was appreciated, since we arrived late in the evening. There was also lots of books and toys that our kids played with everyday before and after we went to explore the island. I would not hesitate to come back and would definitely recommend it to anyone thinking of booking!
Top guest favorite
A clear view of the saltwater pool reflects the blue sky and ocean beyond. A wooden table beside the pool is adorned with a fruit basket and two glasses, suggesting a serene space for relaxation. The surrounding landscape features rolling hills and distant homes.
Villa in Campanário
5 out of 5 average rating, 5 reviews

Arbor Villa: Nature Retreat

CharlotteRating, 5 stars2 weeks ago
Well what can I say about abor villa- By far the best air bnb we have ever stayed in. Absolutely exceptional and decorated beautifully, so artistic and clean and akin to a boutique hotel. Emma was a fantastic host, she made the whole stay exceptional for our young family. Personal touches such as a mini chair for our two year old with suitable cutlery, cups etc ready for us, even taking the trouble to remove the legs of the children’s bed so not too high from the ground. She provided a box of toys for our children and ensured staples were ready for us after a late flight so that the children had food and milk- something we whole heartedly appreciated. The position of the villa was ideal- close to the capital, excellent views , close to restaurants and local towns and ideally situated so easy to get to the northern sites of the island which really wasn’t far when renting a car. Emma was easily reachable and offered lots of recommendations. The pool and views exceptional, we will return!

Luxury villa rentals

Superhost
Two independent villas are positioned harmoniously on a landscaped property. Each villa features an inviting porch and is complemented by infinity swimming pools, surrounded by lounge chairs. A flourishing garden with neatly arranged greenery leads to the edge of the property, enhancing the natural setting.
Villa in Prazeres
5 out of 5 average rating, 3 reviews

Villas Fauna & Flora - Nature & Tranquility - Infinity Pool

ThierryRating, 5 stars10 months ago
The property easily lives up to the description and the pictures. The houses are fully equipped, very nicely decorated and comfortable. The swimming pools offer stunning unobstructed views of the ocean during the day and of the sky at night. There are no road noises, the place is truly calm. Grocery stores are a few minutes away by car, as are restaurants. Numerous hikes can be found in the region. The host is very reactive and will provide many recommandations related to restaurants and activities. Renting both houses to two families is a great way to spend time together while also having some privacy. I would go back there without any hesitation.
Guest favorite
A clear view of the infinity pool is framed by lush greenery and vibrant yellow umbrellas. Comfortable seating aligns beside the pool, offering a relaxed atmosphere with stunning views of the ocean.
Villa in Ribeira Brava
4.82 out of 5 average rating, 28 reviews

Luxury villa for 6 to 8 people, full ocean view

KennethRating, 5 stars3 months ago
Karine and her family have been super sweet and helpful. We were a family of 6 spanning several generations, and the house is perfect for this. Highly recommended. Everything was new and worked flawlessly. Best recommendations from Kenneth.
Superhost
The villa features a modern architectural design with large windows and a vibrant red roof. A spacious swimming pool is encompassed by a well-maintained terrace, furnished with lounge chairs and umbrellas. Lush greenery surrounds the property, enhancing the private outdoor space.
Villa in Sao Goncalo
4.79 out of 5 average rating, 77 reviews

Casa Crerital - By Wehost

MiguelRating, 5 stars1 month ago
The house is extremely well located, in a quiet area with a stunning sea view. It is the ideal place to rest and enjoy the scenery. The house is equipped with everything needed for a comfortable and worry-free stay. It was a great experience — I highly recommend it!
Top guest favorite
The villa's contemporary exterior features a smooth concrete structure with large glass panels and multiple windows. The building is situated on a hillside, surrounded by greenery and offering unobstructed views. The sunset casts warm light on the facade, enhancing its modern design.
Villa in Funchal
4.99 out of 5 average rating, 84 reviews

The Bay House.:full ocean and Funchal bay view

DavidRating, 5 stars2 weeks ago
Fantastic views, really quiet but easy to get to places. Great villa, would be happy to stay again when next in beautiful Madeira
Superhost
A serene infinity pool offers a panoramic view of the ocean and coastal landscape. Two individuals are seen enjoying the warm waters, with lush greenery framing the scene and the horizon blending into the azure sky.
Villa in Funchal
4.95 out of 5 average rating, 21 reviews

Amazing villa FUNCHAL, panoramic sea view

HeleneRating, 5 stars35 months ago
Beautiful, clean, open and inviting home! Jeanne and her family were wonderful hosts! Quick and easy trip into Funchal but so nice to have the privacy! Thank you so much!!
Guest favorite
An outdoor deck is featured, overlooking the ocean with clear views of the rocky shoreline. Comfortable lounge chairs are positioned for relaxation, while potted plants add a natural touch to the wooden deck. The surrounding landscape enhances the serene seaside setting.
Villa in Santa Cruz
4.93 out of 5 average rating, 67 reviews

Santa Cruz Ocean Villa - sea access

SophieRating, 5 stars1 month ago
There was a group of 8 of us and we had the most amazing stay! The location is super close to the airport and the main town making it easy to get around. It is very private house so it feels like your own secluded space. The access to the beach is stunning and the large deck with the pool, sauna and BBQ make a perfect space to hang for the day. Would 100% recommend staying here! Thank you 😊
Guest favorite
The villa showcases a spacious outdoor area featuring a private infinity pool and a well-maintained lawn. Views of the ocean extend in the background, while the house presents traditional architecture with a terracotta roof and whitewashed walls, complemented by nearby greenery.
Villa in Faja da Ovelha
4.98 out of 5 average rating, 59 reviews

Blue Sea Tower, Private Heated Pool. Ocean view

AnniePierRating, 5 stars1 month ago
Dream stay. We even extended our stay because it was too hard to leave this view and these heavenly sunsets. The outdoor space is breathtaking. The accommodation has everything you need. (little echo inside, however, given the ceramic and concrete as the main interior coverings) Faja de Ovelha is very quiet so a car is a must if you want to go to the restaurant or grocery store. We did find a cafe up the hill that was perfect and walkable (if you feel like climbing stairs) From the house it is also possible to access 2 hiking trails that we liked a lot. Communication with the host was really easy and fast! We would highly recommend the Blue Sea Tower.
Guest favorite
A private pool area features a clear blue swimming pool surrounded by stone tiles. Two wooden lounge chairs, adorned with blue and white striped cushions, are positioned beside the pool, inviting relaxation under the sun.
Villa in Ponta do Sol
4.95 out of 5 average rating, 20 reviews

Luxury Haven: Heated Pool, AC & Sun

WilliamRating, 5 stars3 weeks ago
One of the best I’ve ever stayed at. The place was so spacious and open, yet felt like at home and cozy. Everything we needed was readily available/ easily accessible. The home is perched up in Ponta do Sol, so the view is of the homes below, and then the drop off to the ocean. Private pool was clean and big enough for our family of 7. Private parking is a gamechanger anywhere in Portugal, and you have a whole driveway which fit our enormous van. Lots of good hikes in every direction so you never feel like you’re driving too much, everything is about 40 minutes from this location, even the other side of the island. Host was so great responsive despite the hour difference from where she is located. Thank you so much for our stay we loved it.

Villa rentals with a pool

Guest favorite
Villa in Prazeres
4.8 out of 5 average rating, 10 reviews

House with sea view and heated saltwater pool

FerencRating, 5 stars1 month ago
We had a perfect week in Didier's wonderful house and had a great time! It was a very well thought out, well-equipped, clean house, from the kitchen to the pool that ran up to 29 degrees! There was also a gym mattress, kettlebell, and petanque! 😉 It was very easy to get in, without a time series, a very detailed, understandable description, easy, free parking, and want for 2 cars. With large spaces, it's perfect for larger families! Didier was always quick to respond, helpful, friendly!
Top guest favorite
Villa in Paul do Mar
5 out of 5 average rating, 16 reviews

Quinta Marefe - On the stunning west coast

FabianRating, 5 stars1 week ago
This is how AirBNB should be. The house is stacked with everything. How often are you in an Airbnb and they only have 6 plates? Here they have 20+, they have Great knives, tons of kitchenware, enough toilet paper, plenty of dishwasher tabs and also cleaner for the washing machine. Things you normally expect but somehow got lost in the making money machine Airbnb is now. Not here!! A absolute crazy welcome basket (have not had such a big one ever), friendly crew and absolute amazing place - can only recommend
Villa in Estreito da Calheta
5 out of 5 average rating, 3 reviews

Lake House

JulienRating, 5 stars1 month ago
The hosts of this fantastic place welcomed us very nicely. After a tour of the lovely house and garden, they left the accommodation to us to enjoy. They have thought of everything and there is so much in the house to have a carefree vacation. There were local delicacies ready for the whole family. We couldn't think of anything that could be better and loved our stay. The area is very easy to explore from this place and in the afternoon/evening it is then nice to come home to this house. Thank you both!
Villa in Estreito da Calheta
4.83 out of 5 average rating, 24 reviews

Villa de la Ponte by Atlantic Holidays

BenoitRating, 5 stars2 months ago
Beautiful villa with a beautiful view from almost all the rooms. Living room + kitchen space very pleasant. Bed and bathrooms nice. Kitchen well equipped. Very easy to contact the owner and to exchange with him.
Guest favorite
Villa in Madeira
4.97 out of 5 average rating, 37 reviews

Design-Villa by the sea/The Banana House

BenRating, 5 stars3 weeks ago
Great location, very peaceful. Fantastic getaway! Hopefully we’ll be back again!
The image features a modern villa with large glass doors that provide a view of the interior dining area. A sparkling pool is situated in the foreground, reflecting the sky above. Lush greenery is visible in the background, enhancing the tranquil atmosphere.
Villa in Prazeres
5 out of 5 average rating, 4 reviews

Villa Noelia Ocean View

ShaquilleRating, 5 stars2 weeks ago
Amazing property! Loved every moment of the stay. Airbnb fully equipped with everything you need. Marco the host was wonderful and really helped us and made us feel welcomed and offered local spots and helped with everything we needed. Defo recommend and will come back again. Thank you very much for having us
Guest favorite
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 in Arco da Calheta
4.93 out of 5 average rating, 208 reviews

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

RonRating, 5 stars2 weeks ago
I had a very pleasant and good stay at the Hillside Villa. At arrival I got very well received by Elvio at the villa. He explained everything good and gave some tips and advice for my stay. The communication is very good with Mandy an Elvio. Friendly and respons was fast. They give you the feeling your stay is important to them. The Hillside Villa was very clean and very well equipped. The pool is heated and nice also to use on a bit colder day. The garage is big enough for a medium to big size car. The street to the garage is a bit small but doable. So a bit of a challenge with a big size. Further the outside door space was clean and very useable with different place to seat during the day with sun. The neighbors are very nice people. Thank you for everything Elvio and Mandy.
Guest favorite
Villa in Ponta do Sol
4.89 out of 5 average rating, 18 reviews

Heaven's Nest by LovelyStay

MariaRating, 5 stars8 months ago
wonderful place, beautiful views! The house is very modern with great amenities and has everything you need.

Quick stats about villa rentals in Estreito da Calheta

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Rentals with a pool

    40 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Portugal
  3. Madeira
  4. Estreito da Calheta
  5. Villa rentals