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House holiday rentals in Estreito da Calheta

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Popular amenities for Estreito da Calheta house rentals

House rentals with a pool

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 Calheta
5 out of 5 average rating, 6 reviews

Villa Althea by YMR

CurtisRating, 5 stars2 weeks ago
We had a great week! Location is incredible looking out over the ocean. We loved the outdoor space and the big kitchen/living room area. Communication with Kevin was easy. We'd definitely come back!
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 stars4 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
Guest favourite
Home in Paul do Mar
4.87 out of 5 average rating, 62 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 Calheta
4.94 out of 5 average rating, 178 reviews

Casa Cro | Ocean View

JesseRating, 5 stars1 week ago
This place is awesome! Elvio is the best host. Clear instructions and directions (it’s a tricky place to find) but his instructions were perfect. The pool is private and a good home base after lots of hiking. We recommend hiking as early as possible and going back to enjoy the pool later. The restaurant up the mountain from the house is amazing (Calheta Green). And a recommendation from the host. Love this place!
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!

Weekly house rentals

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.
Top Guest favourite
Home in Paul do Mar
4.97 out of 5 average rating, 88 reviews

CASA DA Lev NOVA - Paul do Mar

SergiyRating, 5 stars3 weeks ago
We really had a great week in this house and are just happy with our choice. You come in and feel right at home, almost like a second home, only on holiday. Everything is super clean and the decor is not only cozy, but also practical. The kitchen is well equipped – we enjoyed cooking. Thank you Nelia for the nice welcome and fresh fruit! A real insider tip – we'd love to come back.
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
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 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!
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.
Guest favourite
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 favourite
Home in Sao Vicente
4.94 out of 5 average rating, 31 reviews

Blue Horizon Luxury Villa

ConnieRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay in this lovely home. The view and atmosphere are incredible. We were very comfortable here, and the welcome basket was a very pleasant surprise, perfect for an evening meal. We highly recommend this home if privacy and relaxation is what you are looking for after a long day of hiking and exploring!

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 stars3 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. 😊
Top Guest favourite
Home in Madeira
5 out of 5 average rating, 20 reviews

Casa Avô da Pedra, By OP

KristianRating, 5 stars6 months ago
Absolutely stunning stay! The views were like something out of a postcard—so picturesque, we almost didn’t want to leave. The house was spotless, and every detail was thought of: towels, blankets, shampoo, even spare wood for the outdoor barbecue. There’s AC in every room (though we didn’t need it), plus a washer, dryer, and plenty of supplies like soap and dishwasher pods. The host was incredibly responsive and attentive at all hours. The garage was a bonus, especially in the rainy weather, giving us extra comfort. The area itself is very peaceful and quiet, yet only a short 7-8 minute drive to cafes, restaurants, and shops. If I ever return to Madeira, this is where I’ll stay—no question.
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.
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 stars1 week 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 stars2 weeks 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