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Vacation rentals with a pool in Calheta

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Calheta

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Villa in Estreito da Calheta

4.96 out of 5 average rating, 203 reviews

Casa Palheiro @ Casas Da Vereda

Relax in class at 250 meters high on the sunny South West coast of Madeira, enjoying sunset and ocean views from the heated pool! The Casas Da Vereda are ideally located in a quiet countryside area with nothing but nature between you and the ocean. At 30 minutes drive from Funchal, 5 minutes drive to rock beaches in seaside villages / sand beaches by the marina of Calheta / “levada” walks. Please note that one can rent any combination of Casa Palheiro (T0), Casa Rural (T1), and (Casa Eco T2)!

Rental unit in Arco da Calheta

4.97 out of 5 average rating, 155 reviews

Villa do Pombal 1 , Swimming pool,great sea views

The stunning apartment is located in one of the most sunny parts of Madeira .Villa to Pombal is a two floor building ,that contain two separate apartments. Each apartment have private entrance. It has breathtaking views , allows you to leave all stress behind and enjoy the natural beauty of Madeira. Excellent place to rest with easy access to many tourists attractions. Apartment is located 5 min. drive to sandy Calheta beach. 25 fountain walk begin is about 10min. drive from apartment.

Home in Arco da Calheta

4.98 out of 5 average rating, 175 reviews

Casa Sol e Vista

Villa with a good view and good sunshine throughout the day. The house is located in one of the best places in the parish. It has two bedrooms, living room / kitchen and two bathrooms, with a capacity for 6 people. The house is situated at the top of a hill which makes the house have an extraordinary view. Outside there is a barbecue, a large garden and the swimming pool. Absolute tranquility. Come spend A pleasant vacation in the HOUSE SUN and VIEW. Contact Duarte Paulo

Home in Calheta

4.92 out of 5 average rating, 212 reviews

Spectacular Villa ECO-Fontes

Magical, our dream villa , year of construction: April 2017 and only 1,5km away from the sandy beach of Calheta, supermarket and restaurants. Beautiful and typical maderian cottage house totally reconstructed mainly using the natural vulcanic stone, recycled wood, roof tiles and other materials with 2 bedrooms, 2 bathrooms, private pool, bbq area, pond with koi fish, garden including herb garden, fire pit area and swimming pool. Breathtaking views of sea and nature.

Cottage in Jardim Do Mar

4.98 out of 5 average rating, 163 reviews

Stonelovers® (Heated Pool Optional) - Unit3

Settled in a stunning organic green land, contemplating an amazing sea view, spectacular cliffs, surrounded by pieces of cropland, banana plantations and vineyards, we have found what today is WOODLOVERS. Combining this dream place with our engineering, sustainability, renewable energies and permaculture background, we were pioneers in the construction of the first contemporary 100% WoodHouse in Madeira Island respecting the nature and the natural environment.

Rental unit in Jardim do Mar

4.95 out of 5 average rating, 273 reviews

Uni AIR Studio

Uni AIR is our top floor studio with a balcony that directly overlooks the horizon and the island's shore. Decorated with a bohemian feel, with a bamboo arch holding a dreamcatcher above the bed, this studio has a double bed,a fully equipped kitchen and an ensuite bathroom ensuring all the privacy and tranquility one is seeking. Feel like being on top of it all? Follow the steps up to Uni AIR's private terrace and let yourself enjoy the surroundings.

Home in Arco Da Calheta

4.99 out of 5 average rating, 112 reviews

Villa Bisa Atlantic View ,heated pool

A 2 bedroom villa located in Arco da Calheta. the property has 2 modern style bedrooms, 2 and a half luxurious modern bathrooms,outdoor shower ,new modern kitchen, living room, etc... The property has just been renovated,modern decorated with high quality furniture which is extremely comfortable. The villa also includes cable ,Satellite TV and internet. The property on the outside has BBQ ,pool with a panoramic Seaview ,a nice eating area.

Rental unit in Paúl do Mar

4.98 out of 5 average rating, 151 reviews

Meu Pé de Cacau - Studio Papaia in Paúl do Mar

Meu Pé de Cacau is a tropical fruit garden surrounded by dramatic cliffs to the north-east and the vast Atlantic Ocean to the south-west. Four beautifully designed and sustainably built studios share the property with an infinity pool, social areas and luxurious plantations hosting hundreds of different tropical fruits, planted on traditional agricultural terraces hand crafted in basalt stone.

Cottage in Calheta

4.97 out of 5 average rating, 134 reviews

In peaceful Prazeres | Quinta Inácia Old Cottage

Set on the peaceful rolling hills below the village Prazeres, overlooking the sea, Quinta Inácia is a lovely new complex of apartments in Madeira with 3 Studios, the refurbished Old Cottage, and a lovely heated swimming pool, competently and personally run by the two owners, Daniel and Silvério.

Yurt in Ponta do Sol

4.97 out of 5 average rating, 351 reviews

Mango Yurt ~ EcoGlamping in a Hidden Paradise

Wake up surrounded by tropical banana trees, listening to the waves by the beach and the spring water falling down the waterfall. This new Glamping site in Madeira Island is the perfect spot to relax, camping in comfort & luxury surrounded by nature. More pictures at @cantodasfontes (insta)

Vacation rentals for every style

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Popular amenities for Calheta rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Ponta do sol

5 out of 5 average rating, 13 reviews

Oak tree / Ocean view

Home in Estreito da Calheta

4.86 out of 5 average rating, 122 reviews

Casa do Penique ORGANIC

Home in Santa Cruz

4.93 out of 5 average rating, 235 reviews

Casa do Cristo Rei

Home in Ribeira Brava

4.97 out of 5 average rating, 109 reviews

Casa Velha D. Fernando

Home in Arco da Calheta

5 out of 5 average rating, 14 reviews

Vila Indigo by Escape to Madeira

Home in Ponta do Pargo

4.88 out of 5 average rating, 124 reviews

Casa da Cascata B&B | Casas da Levada

Home in Calheta

5 out of 5 average rating, 6 reviews

Lucky Lemons - Boutique Houses Madeira

Home in Ribeira Brava

4.94 out of 5 average rating, 137 reviews

Sweet Brava Home - Pool & Sea view

Condo rentals with a pool

Condo in Arco da Calheta

5 out of 5 average rating, 31 reviews

Casa Mar Azul 3

Condo in Caniço

4.86 out of 5 average rating, 149 reviews

Family friendly apartment swimming pool ocean view

Condo in Funchal

4.86 out of 5 average rating, 162 reviews

Monumental Apartment

Condo in Funchal

4.88 out of 5 average rating, 139 reviews

Whitehouse408 Sw.Pool & Pvt. Parking

Condo in Estreito da Calheta

4.9 out of 5 average rating, 48 reviews

Alegria Apartment with Pool

Condo in Funchal

4.87 out of 5 average rating, 159 reviews

My Cozy Spot

Condo in Estreito da Calheta

4.6 out of 5 average rating, 10 reviews

Charming Calheta Plaza Penthouse

Condo in Funchal

4.85 out of 5 average rating, 118 reviews

Varandas do Funchal Apartment

Quick stats about vacation rentals with a pool in Calheta

Total rentals
130 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
4.6K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

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