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Family-friendly vacation rentals in Calheta

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Calheta family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in Seixal
4.69 out of 5 average rating, 42 reviews

Gouveia Cottage

SteveRating, 5 stars2 months ago
Stayed for 6 nights in April. The house, it's location and Seixal were all fantastic. The heated pool was a real luxury and brilliant to see it in included in the price.
Guest favorite
Villa in Sao Vicente
4.89 out of 5 average rating, 123 reviews

The Estrelícia-Dourada Garcês House

LisaRating, 5 stars8 months ago
Leonel’s home was beautiful and exactly as pictures. Leonel met us at the property and shared lots about the area and had wonderful recommendations. The house had lots of space for 2 or a family and it is very close to lots of beautiful activities. We had a wonderful stay.
Guest favorite
Home in Ponta do Sol
4.98 out of 5 average rating, 87 reviews

Relax Over The Sea -12391/AL

NiravRating, 5 stars6 days ago
Carlos’s place was fantastic! We really enjoyed our stay – the property was beautiful, comfortable, and exactly as described. The location was perfect, and everything was well taken care of. A special thanks to Carlos for the warm hospitality and helpful communication throughout. Would definitely love to come back someday. Highly recommended!
Guest favorite
Condo in Caniço
4.86 out of 5 average rating, 162 reviews

Family friendly apartment swimming pool ocean view

CathyRating, 5 stars2 weeks ago
The apartment was perfect for our family, a great base to explore the island. Well equipped for a family though we only used for breakfast, eating out in the many local restaurants . The bakery downstairs is fabulous , serving breakfast, lunch and snacks..
Superhost
Apartment in São Martinho
4.82 out of 5 average rating, 38 reviews

Luxury Sea View Apartment

JoannaRating, 5 stars8 months ago
I think this is one of the best scenic app on the island. I have not seen such spectacular sunsets anywhere. The pool is perfect for swimming after tours. There is also a gym, overlooking the ocean that my husband used. The only thing to know is that it's a good idea to bring earplugs because a garbage truck arrives across from the bedroom quite early in the morning. But that shouldn't discourage you from booking. Graca is also a flexible host and allowed us to stay 4 hours longer because we had a late evening flight. Thank you!
Superhost
Apartment in Funchal
4.9 out of 5 average rating, 39 reviews

Apartment Peaceful CC

EmilaRating, 5 stars25 months ago
Leonel is super friendly and helpful. The apartment is clean and in the quiet area. It was hard to leave, especially the SPA and swimming pool :( Big parking space, highly recommended!
Superhost
Home in Madeira
4.82 out of 5 average rating, 49 reviews

Casa Leonor 21119/AL Vistas Deslumbrantes

FranziskaRating, 5 stars4 months ago
We enjoyed the house very much, it has a perfect location, we would book it again anytime.
Superhost
Condo in Funchal
4.89 out of 5 average rating, 181 reviews

Central Garden,heart city,quiet square,marina, P

Brenda & AlanRating, 5 stars2 weeks ago
Great apartment. Everything as described. Tip...bring some shower/bath gel or buy some locally. There was only little bottles of shampoo. This was to start you off when you arrived, but, if you feel like a shower after a long journey it would be nice to have just a couple of small bottles of gel just for the initial shower or bath. It was quite noisy when we stayed with very loud building works with an excavator loading and crashing rocks and boulders into the lorries and travelling right past the apartment loaded with all of those 🥺 This was at the front of the apartment, so although we couldn't use the balcony there: thankfully the bedroom was at the rear of the property, so a lie in was possible when the work started early in the morning. However, this may not be the case for any future guests as they may have finished the works before they arrive. Other than this problem, we had a great time on this beautiful island ( our 8th visit and our first time in self catering)

Family- and pet-friendly home rentals

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.
Superhost
Townhouse in Ponta do Sol
4.83 out of 5 average rating, 204 reviews

Organic Phenomena

AlexandraRating, 5 stars1 week ago
this place was great! it's in a cute area bear ponto do sol, lots of parking, and just a short walk from some hikes. Rodrigo was very helpful and responsive, the place was great, and his cat is so cute and friendly!
Guest favorite
Home in Sao Vicente
4.92 out of 5 average rating, 117 reviews

Pebble Beach House- Casa da Fajã

CathyRating, 5 stars1 month ago
We absolutely loved being right on the ocean! It was within feet of the house!- with the waves crashing and the patio where we ate all our meals, provided an excellent ambiance for our trip. We stayed 6 nights and were so glad we didn’t move around to other places. The promenade next to the house is very scenic and offered a one mile round trip walk along the ocean . Watching the surfers was also a plus.
Guest favorite
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
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 😊🙏
Superhost
Cottage in Madeira
4.9 out of 5 average rating, 152 reviews

Casa dos Anjos 9224/AL

ArjaRating, 5 stars3 weeks ago
The house is perfect. Only minus was the road renovation project, 2 times during our stay. To walk the dog nearby was a small problem, but driving further solved the problem. Veronica answered our questions promptly. Thank you for a good holiday. Small villages nearby are worth visiting, Ponta do Sol as well is very interesting.
Guest favorite
Condo in Câmara de Lobos
4.89 out of 5 average rating, 217 reviews

Village Apartment

BárbaraRating, 5 stars2 weeks ago
The place is in an amazing location. 5-star reception. I'll be back!
Top guest favorite
Apartment in Funchal
4.99 out of 5 average rating, 116 reviews

Encarnacao Funchal, a Home in Madeira

JodyRating, 5 stars1 week ago
We loved the apartment and the location. An easy to walk to the old town . It was clean and Filipe was there to greet us when we arrived. We felt well taken care of. It’s a small thing, but we appreciated having enough paper products for our stay. And thank you for all the delicious fruit you provided!

Family-friendly home rentals with a pool

Superhost
Cottage in Funchal
4.83 out of 5 average rating, 223 reviews

Amazing VILLA, PRIVATE POOL superb

MarkRating, 5 stars1 month ago
We had a great stay at Patricia’s Villa - this was our second visit after staying in 2023. We loved the views and the extra facilities like the pool and games room. The Villa is outside of Funchal but you can be in the town in 10 mins which was great. Patricia is an excellent host who was flexible with check in / check out times to accommodate our flights schedule and was also very helpful with local information. I’m sure we will be back!
Guest favorite
Home in Santa Cruz
4.93 out of 5 average rating, 246 reviews

House of Christ the King

MarcinRating, 5 stars3 weeks ago
The accommodation is great, everything as described and in the photos. It is a bit dated, but we felt very comfortable there. Bruno gave us a very warm welcome and showed us everything we needed to know. When there was a problem with the water pump on the second day, he sorted it out very quickly. We can highly recommend the accommodation.
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
Guest favorite
Villa in Arco da Calheta
4.93 out of 5 average rating, 208 reviews

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

RonRating, 5 stars1 week 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.
Superhost
Home in Ponta do Pargo
4.88 out of 5 average rating, 128 reviews

Casa da Cascata B&B | Levada Houses

AnnaRating, 5 stars6 months ago
This was a delightful place to stay. Very private and so many facilities for a small place. Beautiful views, swimming pool and honesty bar. A total hidden gem.
Top guest favorite
Home in Funchal
4.99 out of 5 average rating, 144 reviews

Casa dos Francelhos, the charming house of Funchal

NinaRating, 5 stars6 days ago
This was by far the best AirBnB we’ve ever stayed in. Antonio was so helpful from the very beginning (he sent lots of info ahead of our arrival), made sure we could check in in the morning after our early flight and welcomed us personally at his lovely house with pool and all amenities one could look for (specifically in the kitchen and bathrooms, where we found all types of equipment, shampoo, tissues etc). The beds were comfortable, the view was stunning. We were a group of 6 and enjoyed cooking together (particularly barbecuing outdoors), but the house offered many peaceful corners for each of us to relax in, too. We also really appreciated Antonio‘s recommendations for hikes and other things to do on the island. Thanks a lot for everything!!
Guest favorite
Home in Ponta do Sol
4.91 out of 5 average rating, 34 reviews

Quinta do Perdigão Peace. Nature. Retreat.

MikkelRating, 5 stars2 weeks ago
We met Hugo, who is super friendly, welcoming, and always ready to help answer questions regarding the home or recommendations for activities and restaurants in Madeira. The home is as described and as shown in the photos - completely clean and beautifully decorated with everything you need for a holiday in a quiet setting. A great stay that I can only recommend others, too.
Guest favorite
Home in Ponta do Sol
4.92 out of 5 average rating, 168 reviews

Casa do Lado

RobinRating, 5 stars1 week ago
We loved our two weeks at this location. Superb views over the ocean and the surroundings. All we needed in the house was present and clean. Very peaceful neighbourhood (although we were a little unlucky to have roadworks ongoing). Amazing private pool (with an extra bathroom)! Carolina was super friendly and always available for questions. Would love to stay here again in the future. Highly recommended!!

Quick stats about vacation rentals that are family-friendly in Calheta

  • Total rentals

    200 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    6.5K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    100 properties have a pool

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Portugal
  3. Madeira
  4. Calheta
  5. Family-friendly rentals