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Vacation rentals with a pool in Estreito da Calheta

Find and book unique homes with a pool on Airbnb

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Popular amenities for Estreito da Calheta rentals with a pool

House rentals with a pool

Guest favorite
A spacious living area features large windows that provide natural light and views of the ocean. Comfortable sofas are arranged around a coffee table, with a flat-screen TV mounted on the wall. Dining seating can be seen through the glass doors, overlooking the pool.
Home in Prazeres
5 out of 5 average rating, 16 reviews

Villa Serenity by Rentallido

ShamisRating, 5 stars2 weeks ago
Absolutely 💯 Amazing host & property
Superhost
Home in Estreito da Calheta
4.85 out of 5 average rating, 137 reviews

Casa do Penique ORGANIC

JulieRating, 5 stars1 month ago
We felt very relaxed and comfortable at Antonio’s lovely house and the garden and views were impressive. We appreciated the interesting features in the garden with its nature feel and enjoyed the pool and sauna which we thought was a real asset for the place. The house is interesting and cared about and Antionio was an excellent and helpful host. We were glad of the car we hired to access shops, restaurants, beach and walking areas as without one would be difficult but it suited us really well as 4 adults who wanted a base from which to explore Madeira.
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, 248 reviews

House of Christ the King

KellyRating, 5 stars1 week 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 favorite
The image showcases a charming stone house with a terracotta roof, surrounded by a wooden fence. A green umbrella sits on a small patio table, providing shade. Lush greenery and distant ocean views are visible in the background, creating a calming outdoor environment.
Home in Ribeira Brava
4.98 out of 5 average rating, 127 reviews

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

NiklasRating, 5 stars2 weeks ago
I loved the beautiful apartment and the view. the highlight was the garden
Guest favorite
An infinity salt-water pool is visible, with a seamless connection to the ocean beyond. Palm trees frame the pool area, while clear blue skies and tranquil waters enhance the serene setting. A boat can be seen in the distance on the horizon.
Home in Paul do Mar
4.87 out of 5 average rating, 62 reviews

The Sunset Avenue w/infinity pool(optional heated)

SigridRating, 5 stars3 weeks ago
The place was just great and exceeded our expectations! The house is really huge, you have plenty of space and privacy, even if you travel as a group. The pool was heated at our request and the temperature was very pleasant. Simply a dream when you can watch the sunset while lying in the pool. The amenities were also great, everything we needed was there. In addition, a garage, we were able to 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 motorcycle drivers who are not exactly quiet. But it was still fine. Overall, the accommodation is highly recommended and the landlord is very friendly.
Guest favorite
Home in Calheta
4.94 out of 5 average rating, 178 reviews

Casa Cro | Ocean View

JesseRating, 5 stars2 weeks 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!
Top guest favorite
A modern villa is showcased with clean architectural lines and large glass windows, surrounded by a manicured lawn featuring palm trees. An outdoor dining table and chairs are arranged on a patio adjacent to the heated infinity pool, overlooking scenic views of the landscape.
Home in Madeira
4.99 out of 5 average rating, 73 reviews

Panoramic View: Lux 3 bed w/ heated pool

DavidRating, 5 stars1 week ago
A great property, spotlessly clean with wonderful views & very helpful hosts. My family & I thoroughly enjoyed our stay.
Top guest favorite
A stone house with traditional architecture is framed by lush banana trees. In the foreground, a spacious pool reflects the sky, accompanied by two sun loungers under a shaded umbrella. The surrounding terrace is paved, creating an inviting outdoor space for relaxation.
Home in Ponta do Sol
4.99 out of 5 average rating, 165 reviews

Typical house above the sea

KarenRating, 5 stars2 days ago
The outdoor area is done very nicely and is just beautiful. Inside is traditional and lots of space. Simple things that u take for granted like water pressure and having good hot and cold water was very good so could have a nice shower. Also most important for me is having a quiet place to sleep which it was and shutters on windows meant u could get it nice and dark. Glad I picked this area as Funchal was clouded over quite a lot over our stay but being south coast meant we got the sun. Enjoyed the 20 min walk in ponta da Sol which is quaint and lovely.

Condo rentals with a pool

Superhost
A serene swimming pool is illuminated at night, reflecting blue light across its surface. Lounge chairs are positioned around the pool, while distant lights from nearby buildings create a cozy backdrop against the dark sky.
Condo in Funchal
4.83 out of 5 average rating, 166 reviews

Bright Ocean Front Apartment

OleksandrRating, 5 stars2 weeks ago
Annikka is a very friendly host. Always answered quickly to our questions. The apartment corresponded to its description. Stunning view of the ocean from the balcony. Nearby are beach resorts, a promenade along the sea, a large shopping center. Convenient access to the city center.
Superhost
An elevated view reveals a lively coastal area featuring a blend of residential buildings and commercial spaces. The ocean shimmers in the background, while a roundabout with palm trees and traffic flows is visible in the foreground, creating a vibrant atmosphere.
Condo in Funchal
4.84 out of 5 average rating, 117 reviews

COSY STUDIO AT LIDO WITH POOL

CharlotteRating, 5 stars1 month ago
We had a lovely stay. The accommodation is very well located, clean and functional. It's very easy to match with Ana. Thanks to her for her warm welcome. Recommended. Charlotte and Romain
Top guest favorite
A salt-water swimming pool is situated in a tranquil outdoor space, overlooking the sea. Lounge chairs and an umbrella provide comfortable seating. Lush greenery surrounds the area, and a smooth patio surface enhances the relaxing atmosphere.
Condo in Arco da Calheta
5 out of 5 average rating, 44 reviews

Casa Mar Azul 3

JaydeRating, 5 stars3 weeks ago
Our experience here was paradise on earth. Breathtaking view from the property and lovely space overall. Sergio is an amazing host, very hospitable and friendly. We hope to be back at some point
Guest favorite
Condo in Funchal
4.94 out of 5 average rating, 119 reviews

Luxury Big Apartment/Ocean view/Free Parking

RobertRating, 5 stars6 days ago
This was the best air BnB I've stayed in, the apartment and view from the balcony were beautiful, and the location was perfect with it being only a ten minute drive from city center. Would definitely recommend!
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
4.87 out of 5 average rating, 164 reviews

Family friendly apartment swimming pool ocean view

Rakhesh AnandRating, 5 stars3 weeks ago
Lovely host and a very well maintained apartment . Very safe private parking lot with variety of restaurants in the neighbourhood
Guest favorite
A vibrant pool area is surrounded by sun loungers arranged neatly along the tiled deck. A modern building stands in the background, providing a welcoming residential atmosphere. Lush greenery and additional structures can be seen nearby, contributing to a relaxed outdoor environment.
Condo in Funchal
4.89 out of 5 average rating, 160 reviews

Whitehouse408 Sw.Pool & Pvt. Parking

StelaRating, 5 stars3 days ago
The host was incredibly helpful and friendly, sent us many local restaurant recommendations, very responsive. Totally recommend booking this place on your next trip!
Guest favorite
A serene pool area is depicted, featuring a clear blue swimming pool surrounded by sun loungers. The loungers are arranged neatly on a wooden deck, with palm trees and lush greenery visible in the background, enhancing the inviting atmosphere.
Condo in Funchal
4.99 out of 5 average rating, 101 reviews

New dream luxury appartment in the Madeira Palace.

OliviaRating, 5 stars3 days ago
Can’t recommend enough. Clean, fantastic space, great location. Marina really helpful and always responsive. Well equipped kitchen with everything for meals in but equally a 10 minute drive into Funchal. The view from the apartment is beautiful and the location means everything is easily accessible. Supermarket across the road. We didn’t hire a car because the location was so great.
Superhost
A large swimming pool is surrounded by lush greenery, offering a serene atmosphere. The clear water reflects the blue sky and clouds above. Sun loungers are positioned nearby for relaxation, enhancing the overall tranquil environment.
Condo in Funchal
4.85 out of 5 average rating, 169 reviews

My Cozy Spot

GiuliaRating, 5 stars1 month ago
Daniel is a very friendly and attentive host. She followed us from the first to the last minute, giving tips about the area. The apartment is really space and spacious, with two nice balconies perfect for an outdoor breakfast!

Quick stats about vacation rentals with a pool in Estreito da Calheta

  • Total rentals

    130 properties

  • Nightly prices starting at

    G$4,184 GYD before taxes and fees

  • Total number of reviews

    3.5K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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