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Family-friendly vacation rentals in Estreito da Calheta

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Estreito da Calheta family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A heated swimming pool is surrounded by a stone wall, featuring lounge chairs positioned for relaxation. The clear blue sky and sunlight enhance the inviting atmosphere of the pool area, while a green umbrella provides shade nearby.
Home in Seixal
4.69 out of 5 average rating, 42 reviews

Gouveia Cottage

SteveRating, 5 stars1 month 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
The image captures a clear swimming pool reflecting the blue sky, surrounded by a well-maintained lawn and mountains in the background. Lounge chairs are positioned near the pool, offering a relaxed setting. A jacuzzi is visible, integrated within the pool area for leisurely enjoyment.
Villa in Sao Vicente
4.89 out of 5 average rating, 123 reviews

The Estrelícia-Dourada Garcês House

LisaRating, 5 stars7 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
A spacious infinity pool overlooks the coastline and ocean, surrounded by sun loungers and palm trees. The house features large glass doors that provide stunning views of the surrounding landscape. The tranquil setting highlights the connection between the property and its natural surroundings.
Home in Ponta do Sol
4.98 out of 5 average rating, 85 reviews

Relax Over The Sea -12391/AL

CarolineRating, 5 stars1 month ago
Three generations from Granny at 67 to 4 year old grandson had a wonderful stay in this lovely house. So spacious with smaller seating areas for a little quiet time, fantastic pool and views of the ocean and sunsets. Shady spots in the garden or full sunshine and beautiful outside dining area. The kitchen was big enough for us all and the open cooking fire a bonus to our barbeque fan. It was well equipped with plenty of cutlery, glasses, etc. Lovely welcome fruit bowl - the bananas were the best ever - milk, cake, wine, beer, teabags, condiments and dishwasher tablets all there ready for us. The back kitchen with washing machines and drier and a brilliant sink for scrubbing muddy shoes after one of our lavada walks. Perfect Granny and Grandad suite on ground floor with huge shower, multiple bathrooms on the other floors and Maria stayed to help us reconfigure the beds to fit our family groups. A car is essential to get the most out of this beautiful island. We loved it - thank you!
Guest favorite
A balcony scene features a table set with two plates of breakfast alongside a scenic view of the ocean. Two chairs are positioned around the table, and the horizon is visible under a clear blue sky, reflecting the sunlight.
Condo in Caniço
4.86 out of 5 average rating, 161 reviews

Family friendly apartment swimming pool ocean view

PeterRating, 5 stars3 weeks ago
Well located accommodation. Small supermarket and bakery very close. As well as restaurants where you could eat. Everything available for a carefree holiday. Airport and Funchal are less than a 15-minute drive away.
Superhost
The outdoor area features a large swimming pool with a clear blue water, surrounded by a sunny deck and palm trees. The ocean is visible in the background, along with rocky cliffs and a clear blue sky, enhancing the scenic coastline.
Apartment in Funchal
4.82 out of 5 average rating, 38 reviews

Luxury Sea View Apartment

JoannaRating, 5 stars7 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
A spacious living area features a large, comfortable sofa in soft grey, accompanied by a modern entertainment unit and a flat-screen TV. Natural light filters through sheer curtains, illuminating a glass dining table adorned with decorative plants and artwork in the background.
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
A modern Jacuzzi is situated under a wooden pergola, surrounded by landscaped greenery. Views of the ocean are visible in the distance, providing a serene backdrop. The outdoor area features smooth decking and natural stone walls, enhancing the relaxing environment.
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.
Guest favorite
The villa's exterior is showcased, featuring a modern design with large windows. A spacious wooden deck surrounds the property, offering various lounge chairs and the swimming pool, while unobstructed views of the Atlantic Ocean create a serene backdrop.
Villa in Caniço
4.89 out of 5 average rating, 62 reviews

Fonte do Mar 1

HannaRating, 5 stars4 weeks ago
Great house for large groups

Family- and pet-friendly 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 stars2 weeks ago
Great house, even better garden! We had a very pleasant stay.
Superhost
A central view of the neighborhood illustrates a vibrant street scene with nearby restaurants and shops. An included map highlights local attractions, including the Farmers Market. Images of the interior showcase various living areas, emphasizing functionality and comfort with a focus on spaciousness.
Condo in Funchal
4.85 out of 5 average rating, 109 reviews

Anadia, Old Town, Funchal, Best Value on Island

MahindraRating, 5 stars1 month ago
We had a fantastic stay in this cozy apartment right in the center of Funchal. The location couldn’t be better — just a few minutes' walk to the centre, restaurants, shops, and the beautiful waterfront. It made exploring the city super easy and convenient. The apartment was well-equipped and comfortable, with everything we needed for a relaxing stay. The host was friendly and responsive. Despite being in the heart of the city, it was surprisingly quiet at night, and the balcony was a lovely bonus for morning coffee or evening wine. Would recommend this place to anyone looking to explore Funchal on foot and experience the local vibe!
Superhost
A panoramic view of a lush hillside is presented, showcasing a collection of colorful homes with terracotta roofs nestled among verdant banana trees. The sky features a mix of clouds and sunlight, enhancing the vibrant landscape of Ponta do Sol.
Townhouse in Ponta do Sol
4.83 out of 5 average rating, 202 reviews

Organic Phenomena

ÉmilieRating, 5 stars2 weeks ago
Rodrigo's place is perfect if you are looking for a calm and peaceful environment. Everything is as described; a fully equipped kitchen, comfortable beds, and a nice view! Rodrigo answered quickly to my questions, and as been kind enough to come pick me up at Café Xavier because I couldn't find the place. One tip: put "Organic Phenomena" in your Google Map to make sure you get the right direction from the airport. Once you know where the place is, it's easy to get there. If you don't have a car and travel with the local bus, expect a long and steep walk from the bottom of Ponta do Sol to the apartment. In a nutshell, our time there as been PER-FECT and I would 100% recommend this place. It's clean and cozy, you got everything you need, plus, Bichana the cat is so lovely!!! She definitely was a part of "our family" while staying there!
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, 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
An outdoor dining area is visible with wooden tables and chairs positioned against a stone wall. The ocean stretches out in the background with gentle waves, and a coastal rock formation creates a picturesque horizon under a clear blue sky among swaying trees.
Cottage in Casas Próximas
4.89 out of 5 average rating, 246 reviews

Casa da Praia

AnoukRating, 5 stars3 weeks ago
Amazing location in picturesque village
Superhost
A wooden table with two cups and a plate of pastries sits on a balcony overlooking the ocean. A pair of binoculars rests nearby, and the bright sky reflects the serenity of the seaside location.
Home in Faja Da Ovelha
4.8 out of 5 average rating, 138 reviews

Casa da Ovelha, your bright and quiet house

SarahRating, 5 stars8 months ago
We had a great stay and the location is sensational. There was everything you needed and we were also set up the travel cot before arrival.
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, 133 reviews

Sofia's Place

GlennRating, 5 stars1 month ago
Hi Sofia! Thank you for the use of such a beautiful home and so lovely to meet you and hear about your life. We will miss Sofias place but will always have the many wonderful memories close to our hearts. 🥰
Superhost
A bright terrace features two lounging chairs positioned for relaxation under the sun. A small wooden table is nearby, surrounded by lush banana plants that provide a tropical backdrop and a sense of privacy.
Cottage in Madeira
4.9 out of 5 average rating, 152 reviews

Casa dos Anjos 9224/AL

ArjaRating, 5 stars1 week 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.

Family-friendly home rentals with a pool

Superhost
A spacious veranda features a terracotta roof offering shade, with views of the blue sea and Funchal harbor in the background. Potted plants and local flowers enhance the outdoor area, which is elegantly paved with stone.
Cottage in Funchal
4.83 out of 5 average rating, 223 reviews

Amazing VILLA, PRIVATE POOL superb

MarkRating, 5 stars3 weeks 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!
Top guest favorite
Villa in Funchal
4.93 out of 5 average rating, 75 reviews

Luxury Villa in City Center Private Pool & Rooftop

DavidRating, 5 stars2 weeks ago
Really lovely accommodation with great views. The host was very responsive and was super helpful when we had a bit of an emergency. Highly recommended.
Guest favorite
A refreshing swimming pool is visible, with its clear blue water reflecting sunlight. Two modern black seating chairs are positioned nearby, offering a view of the vast ocean. The surrounding area features a sleek railing, enhancing the open atmosphere.
Home in Santa Cruz
4.93 out of 5 average rating, 246 reviews

House of Christ the King

MarcinRating, 5 stars1 week 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
An infinity pool surrounded by lush green landscaping reflects the sky at sunset. The pool features a unique stone design with sections that blend into the natural scenery. Water lilies and small plants are visible in a lower section, enhancing the tranquil outdoor setting.
Home in Ponta do Pargo
4.88 out of 5 average rating, 128 reviews

Casa da Cascata B&B | Levada Houses

AnnaRating, 5 stars5 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
A private outdoor space features a swimming pool surrounded by sun loungers under palm trees. The house's vibrant exterior, with red accents, is complemented by blooming flowers and greenery, creating a relaxing atmosphere for guests to enjoy.
Home in Funchal
4.99 out of 5 average rating, 143 reviews

Casa dos Francelhos, the charming house of Funchal

RoseRating, 5 stars2 weeks ago
We had a wonderful stay at Casa dos Francelhos! The house is beautiful and spacious. António was very hospitable and welcoming throughout, providing us with recommendations, fruit, wine, and local delicacies on arrival! We had such a lovely trip to Madeira and that was in no small part due to our stay at Casa dos Francelhos.
Guest favorite
Home in Calheta
4.94 out of 5 average rating, 176 reviews

Casa Cro | Ocean View

AnaRating, 5 stars1 month ago
The house was great and the outdoor area with the swimming pool and the barbeque was amazing. Most of our meals were there and we loved it! You definitely need a car to reach the house and to move around, but if you are ok with it, I totally recommend this place. Many great walks/levadas, the sandy beach of Calheta and the beautiful Paul do Mar are within easy reach with a car too.
Guest favorite
A rooftop swimming pool features a clear blue water surface, reflecting the surrounding sky. A railing surrounds the pool, providing safety and unobstructed views. The pool area allows for relaxation and enjoyment of the outdoor setting.
Condo in Funchal
4.91 out of 5 average rating, 128 reviews

Charming Lido Flat I

VickyRating, 5 stars4 days ago
Thank you Ana the apartment was absolutely perfect for our family of 4! brilliantly spacious, beautiful sea and restaurant views from the balcony, private sunbathing balcony and an almost private pool on the rooftop. the location is perfect to walk down to the seafront or to funchal centre. with brilliant buses just across the road. A really well stocked supermarket is a few minutes walk away and a well equipped kitchen made it super easy to cook at the apartment. I really reccomend Anas apartment we would certainly come back to wlexplore more of the beautiful island. Ana was a perfect host with a wonderful welcome pack when we arrived. Thank you again!
Superhost
Guest suite in Funchal
4.74 out of 5 average rating, 31 reviews

Live inside a traditional Quinta

RachelRating, 5 stars38 months ago
I stayed at the Quinta for one week on a solo holiday. The room was well equipped so I could cook meals for myself, the grounds of the house are lovely and peaceful and the walk to town and back is quite short and straightforward (yes it’s steep but everywhere is). Free plentiful parking was a huge bonus as I did a lot of driving around the island, it is also quite easy to find coming off the motorway. Helena and Roberto were very welcoming and accommodating as hosts. If you are looking for a place to relax and enjoy Madeira & Funchal this is a great place to stay. Local bakery has the best pasteis de nata that I tried on the island (a lot!).

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

  • Total rentals

    190 properties

  • Nightly prices starting at

    $20 before taxes and fees

  • Total number of reviews

    5K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    100 properties have a pool

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

Destinations to explore