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House holiday rentals in Estreito da Calheta

Find and book unique houses on Airbnb

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Popular amenities for Estreito da Calheta house rentals

House rentals with a pool

Guest favourite
Home in Jardim do Mar
4.94 out of 5 average rating, 52 reviews

Paradise by the sea | Jardim. Meu Amor!

FransRating, 5 stars2 weeks ago
A great beautiful house to explore Madeira from. Very complete and stylishly furnished. Super friendly welcome with good explanations and tips. We are spoiled with delicious snacks and a nice bottle of wine. 5 stars on all parts, super deserved!! Highly recommended.
Guest favourite
Home in Santa Cruz
4.93 out of 5 average rating, 248 reviews

House of Christ the King

KellyRating, 5 stars3 days ago
What a wonderful place to stay and for us perfect location to explore beautiful Madeira. 6 of us stayed for 1 week, the accommodation was perfect with various areas to spread out. We spent most of our evenings around the pool side, playing games and soaking up the views. The home has everything a family would need to enjoy your stay. Local shops, cafes and restaurants 10min walk up hill. Fully recommend if you are able to take a 1 day jeep tour of the island as Madeira has some spectacular scenery, valleys, mountains, villages and locations to explore. Contact with the host was effortless and always quick with responding. We loved our stay.
Top Guest favourite
Home in Ribeira Brava
4.98 out of 5 average rating, 127 reviews

Casa Velha D. Fernando (Old House D. Fernando)

NiklasRating, 5 stars1 week ago
I loved the beautiful apartment and the view. the highlight was the garden
Superhost
Home in Funchal
4.84 out of 5 average rating, 134 reviews

Ocean View Villa Madeira

HarpreetRating, 5 stars2 weeks ago
Pedro is the best thing about this place the man is a legend really kind and helpful goes over and beyond. The place is so nice pool is amazing with fantastic views. I can not fault the place. Over three floors we had 12 people in it and didn’t feel cramped. Book this place you will not regret it
Top Guest favourite
Home in Arco da Calheta
5 out of 5 average rating, 17 reviews

Vila Bela

MauroRating, 5 stars1 week ago
Everything was perfect! The host was super friendly. Check-in was smooth and welcoming, the place was clean and exactly as described. When we had a small issue, the host responded quickly and solved it right away. Check-out was just as easy. Would definitely stay again!
Guest favourite
Home in Paul do Mar
4.87 out of 5 average rating, 61 reviews

The Sunset Avenue w/infinity pool(optional heated)

SigridRating, 5 stars2 weeks ago
The accommodation was simply great and exceeded our expectations! The house is really huge, you have a lot of space and privacy, even if you are traveling as a group. The pool was heated at our request and the temperature was very pleasant. It's simply a dream to be able to watch the sunset while lying in the pool. The amenities were also great, everything we needed was there. In addition, a garage, we could park the second car in front of the gate. The location was quiet, only on weekends there is a lot going on in the restaurants at the end of the street, also many motorcyclists who are not exactly quiet. But it was still fine. Overall, the accommodation is highly recommended and the landlord is very friendly.
Guest favourite
Home in Campanário
5 out of 5 average rating, 21 reviews

Villas Calhau da Lapa 10

DanielleRating, 5 stars2 weeks ago
Such an amazing space! Our family highly enjoyed our stay. The home is more beautiful than the pictures. The pool was lovely and the location was great for hiking as well as trips to Funchal. We would love to come back again!
Top Guest favourite
Home in Madeira
4.99 out of 5 average rating, 72 reviews

Panoramic View: Lux 3 bed w/ heated pool

MoustafaRating, 5 stars1 week ago
This place exceeded all expectations. The apartment was spotless, modern, and very comfortable. Everything was exactly as shown in the photos—if not better. The location was great, with easy access to everything I needed, but still peaceful and quiet. The host was welcoming, responsive, and made check-in super easy. I really appreciated the thoughtful touches throughout the space. It felt like a true home away from home. I would absolutely stay here again and highly recommend it to anyone visiting the area!

Weekly house rentals

Guest favourite
Home in Prazeres
5 out of 5 average rating, 14 reviews

Villa Serenity - Private Pool & Sea View

AubreyRating, 5 stars2 weeks ago
This place is beautiful and peaceful. It is about an hour drive from Funchal, but there are lots of little towns all along the way. We had a wonderful stay.
Guest favourite
Home in Jardim do Mar
4.92 out of 5 average rating, 48 reviews

Welcome to Little Hawaii!

BrittaRating, 5 stars3 weeks ago
There were only two of us, which is almost too little for this beautiful house. Everything was great, new, well maintained. Very tasteful and beautifully decorated. It was hard to leave because the house was so beautiful. In the evening, a very nice view of the sunset.
Guest favourite
Home in Paul do Mar
5 out of 5 average rating, 13 reviews

Wave Shadows Beach House

DanielRating, 5 stars3 weeks ago
If you’re looking for a quiet coastal cottage in Madeira this place is perfect. The view is beautiful with restaurants right around the corner. You’re steps away from the beach and beautiful hiking trails. The house is small but well kept and was very comfortable for two guests
Guest favourite
Home in Arco da Calheta
5 out of 5 average rating, 17 reviews

Sea View

Atelier D'Art OgwilowRating, 5 stars2 weeks ago
Fatima welcomed us very well, local products were available in the house, the view of the sea and the mountain is exceptional, everything is very quiet for resting. thanks Fatima
Superhost
Home in Calheta
4.83 out of 5 average rating, 41 reviews

Casa Dos Velhos

AmandineRating, 5 stars1 week ago
Very well decorated accommodation matching the photos. The hosts are extremely responsive and caring. If you have a comment, you can be sure that they will do their best to resolve it. Small downside on the kennel which is certainly on the other side of the valley because the dogs bark. But it remains occasional, about 3-4 times a day for 10 minutes, it is not continuous (at feeding time?). There are also a lot of critters that come every day (centipedes and we had a few cockroaches). The apartment was however very clean when we arrived. I think they get in because there is a gap between the doors and the floor. A seal might help. But it's easy to put outside with a scraper and it's the countryside, so it's understandable. Apart from these minor issues, we loved our accommodation and recommend it, hence the 5 stars!
Guest favourite
Home in Calheta
4.94 out of 5 average rating, 16 reviews

The Star House -Jacuzzi & Aircon

KevinRating, 5 stars2 weeks ago
We had a fantastic stay at this beautiful, modern Airbnb! The apartment is brand new and stylishly furnished, with everything you could possibly need—especially the fully equipped kitchen, which was a dream to cook in. The highlight was definitely the private whirlpool—perfect for relaxing after a long hiking day. We were warmly welcomed by the property manager, Charlene, who allowed us an early check-in and made sure we felt right at home. Both Charlene and the host, Jose, were incredibly responsive and helpful throughout our stay. The place is also extremely baby-friendly, with a lovely play corner and even a few thoughtful gifts for our 7-month-old baby. We truly appreciated the sweet welcome gifts for us as well.
Top Guest favourite
Home in Jardim do Mar
5 out of 5 average rating, 23 reviews

House 7 in Jardim do Mar, Calheta

JamesRating, 5 stars3 weeks ago
We had a fantastic stay at Filipe’s home, which is beautiful and really thoughtfully designed. It’s very well appointed, spotlessly clean and in a very charming little village away from the hustle and bustle of Funchal, but still accessible by car. Communication was excellent and the fruit and biscuits were a lovely touch. Highly recommended.
Top Guest favourite
Home in Calheta
4.98 out of 5 average rating, 80 reviews

Zeza´s Garden

MarleenRating, 5 stars3 weeks ago
This place is very nice! It has a beautiful view, on a quiet street with a lots of privacy. Inside was bigger than we expected and very cosy. It has everything you need and we really felt at home and relaxed. There is a steep but short walk directly to the center, with some good restaurants and a grocery store. Zeza is very responsive, enthusiastic and friendly. If we go back to Madeira, we will come back!

Private house rentals

Guest favourite
Home in Arco da Calheta
4.91 out of 5 average rating, 22 reviews

Magnificent villa with a heated pool

JuliaRating, 5 stars2 weeks ago
Highly recommend! We had a fantastic time at this beautiful Airbnb! The house is a dream – very large, clean and with great amenities. Particularly noteworthy are the fantastic pool, the well-maintained outdoor area and the breathtaking view of the sea, which makes every morning a highlight. A special thank you goes to Tatjana and Ana. She was incredibly friendly, always helpful and made the stay even more pleasant with her excellent service. The check-in and check-out went completely smoothly, and the contact was also uncomplicated and professional at all times. We highly recommend this Airbnb and would come back anytime! Thank you for an unforgettable stay. 😊
Guest favourite
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.
Superhost
Home in Arco da Calheta
4.86 out of 5 average rating, 14 reviews

Casa Requinte - Hot tub

BobbyRating, 5 stars3 weeks ago
absolutely beautiful place, house was immaculate and was very secluded! Rosa was responsive and very helpful!
Guest favourite
Home in Arco da Calheta
4.94 out of 5 average rating, 17 reviews

Tropical Garden 1

DavidRating, 5 stars1 month ago
Beautiful cottage in a very quiet location, ideal for relaxing. Private parking, well equipped kitchen and very comfortable beds. On the terrace, the sun shines until 9 pm with a view of the sea and the mountains.
Guest favourite
Home in Fajã da Ovelha
4.86 out of 5 average rating, 28 reviews

The House of Passion

IrisRating, 5 stars6 days ago
We were very satisfied and felt extremely comfortable. The view from the bedroom and balcony is a dream. The house is really big, the kitchen is very well equipped and you have a lot of privacy. Yamila is friendly and always available. We will be happy to come back!
Top Guest favourite
Home in Estreito da Calheta
5 out of 5 average rating, 83 reviews

Villa Nature and Sun

EmilyRating, 5 stars3 weeks ago
We loved our stay at Noélia’s place- she thoughtfully left food for us and wonderful pasteis de nadas on our arrival!
Top Guest favourite
Home in Fajã da Ovelha
5 out of 5 average rating, 18 reviews

Chalet do Massapez

AstridRating, 5 stars2 weeks ago
We had a lovely stay in Madeira at this property. Lovely facilities throughout the place, with the pizza oven, jacuzzi and the hammock (our favourite) all very nice additions to the property which were thoroughly enjoyed during our stay. We opted not to heat the pool but the temperature was fine to swim in anyway! In terms of location the area is very peaceful and scenic however at the cost of activities often being a slightly further drive. We did not find this to be an issue throughout our stay however! Definitely recommend renting a car if staying here!
Guest favourite
Home in Estreito da Calheta
4.87 out of 5 average rating, 67 reviews

Tia Maria Cottage

ClémentRating, 5 stars1 week ago
We had a very peaceful journey at Juan’s cottage! At the top of a typical village on the island. Juan was very friendly, reactive and with good advice. Obrigado !!

Quick stats about house rentals in Estreito da Calheta

  • Total rentals

    100 properties

  • Nightly prices starting at

    $31 AUD before taxes and fees

  • Total number of reviews

    3.2K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore

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