
Holiday rentals with a pool in Ponta do Sol
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Top-rated rentals with a pool in Ponta do Sol
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Uni WATER Studio
Wake up to absolute mind blowing scenery in this mezzanine featuring floor to ceiling high windows facing the island's stunning coastline, often requiring a second look to truly appreciate the beauty that this magnificent island has to offer. The mezzanine accommodates two people, has an ensuite bathroom, a fully equipped kitchen and also has access to its own private garden. Needless to say, our infinity pool is also there for you to enjoy and relax. Free parking is available in Jardim do Mar.

Casa Palheiro @ Casas Da Vereda [Thatched-Roof House]
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)!

Old Wine Villa
Welcome to Paradise! Come stay at our cozy Villa with a splendid Atlantic ocean view by the infinity pool! This house was first built in 1932 and since then it has been know as "Casa do Vinho Velho", "The Old Wine House". My great-grand mother used to tell stories about the old man "Vinho Velho" and his passion for his wine and agriculture. The house has been updated but we have kept old features, like an old brick oven in the kitchen and 3 stone rocks for vine hanging in the living room!

Casa Miradouro Loft - Pool by Stay Madeira Island
Stay Madeira Island presents Casa do Miradouro Loft. The ideal place to rest, relax, forget the routine and stress, all in one space! The accommodation has been prepared to offer you the perfect stay on Madeira Island. It is located on the southern coast of the island, in Ribeira Brava. This serene and spacious space is waiting for you! [Pool heating available upon request; extra cost of €25 per night; minimum stay (requested upon booking or up to one week prior to arrival)].

Mango House
House with superb sun exposure, peaceful and stunning views over the sea and the mountain. Has 2 bedrooms (one with a double bed and the other with two single beds easily convertible into a double bed), a complete bathroom. On the ground floor open space with kitchen / living and dining room and toilet. Furniture and careful decoration. Outside enjoy the garden and the pleasant dining space with incredible views of the sea. The barbecue, mini-pool and shower complete your well-being.

☀️ Bright & Spacious w/ Pool & Oceanside View :D
Modern studio in the sunny and serene coastal village of Jardim do Mar, south west of Madeira Island. Studio D features an open plan design with kitchenette, lounging area, TV (with Netflix), a cozy queen size bed, a spacious bathroom with washing machine and a private balcony with ocean and pool view (24° to 26° Celsius). Guests have full access to the garden and heated saltwater pool. New Tourism Tax already included in the price, so we'll take care of that for you.

Papaia Yurt ~ EcoGlamping in a Hidden Paradise
Wake up in total privacy, surrounded by a lush permaculture garden where you can see, taste and smell nature’s abundance. At Canto das Fontes, in the sunny Sítio dos Anjos, it feels like eternal spring all year — even when other parts of Madeira are cooler. An award-winning regenerative eco-glamping where sustainability meets comfort and luxury, with a natural pool, Honesty Bar and stunning views of the sea and waterfall. 💧🌿 More pictures and vibes: @cantodasfontes

Woodlovers Jardim® (Heated Pool Optional) - Unit 1
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.

Anjos Paradise Nest
Anjos Paradise Nest is a Mezzanine Studio, decorated with a special touch, designed to be the cozy place to return to after a day exploring our beautiful island. It features a fully equipped kitchen , a living room area, and on site parking, within walking distance of the amazing waterfall Cascata dos Anjos. Enjoy a swim in the pool and a meal in the garden at sunset, overlooking the horizon, in perfect communion with the Nature surrounding you.

Meu Pé de Cacau - Studio Papaya 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.

Villa Miradouro da Baleia by PAUSA Holiday Rentals
This magnificent, modern, private villa Miradouro da Baleia (Whale Watchtower) has some of the best ocean and mountains views on the island, with a infinity pool and located in a premium spot surrounded by spectacular cliffs, cropland, banana plantations and vineyards, it was carefully & tastefully restored/built in 2018 offering a unique experience of a Portuguese summer style accommodation!

Typical house above the sea
"Casa Nambebe" is a typical Madeiran house. Situated on the south slope of Madeira island, it is a great place to relax and enjoy a beautiful view of the sea. The house is placed in the middle of a land of banana trees where the contact with nature is immediate and the infinite pool will have you feel like you're in the ocean. Every sunset is unique. Número de licença ou registo 38381/AL
Popular amenities for Ponta do Sol rentals with a pool
House rentals with a pool

Rochinha house with pool and fabulous view

House of Christ the King

Place In The Sun

Peak A Boo (Private Heated Pool & Private Parking)

Casa Cro | Ocean View

Luxury Villa Pérola

Villa Bisa Atlantic View ,heated pool

Villa Panorama - Luxury Villa with Jacuzzi-Calheta
Apartment rentals with a pool

Ocean View Madeira Apartment

Spectacular Ocean and Cliff views with Pool

COSY STUDIO AT LIDO WITH POOL

Casa Mar Azul 3

Luxury Big Apartment/Ocean view/Free Parking

Family friendly apartment swimming pool ocean view

Monumental Apartment

Whitehouse408 Sw.Pool & Pvt. Parking
Other holiday rentals with a pool

Vila Inanda - Apartment 3

Cottage Tenda, studio suspended over the ocean

Wander Sunshine Deluxe C

The Tree of Life House

Tabua Lodge

Villas Calhau da Lapa 10

Casa da Arvore in the Eucalyptus Forest, no neighbors

Beige Rock Villa
Quick stats about holiday rentals with a pool in Ponta do Sol

Total holiday rentals
Explore 80 holiday rentals in Ponta do Sol

Nightly prices starting at
Ponta do Sol holiday rentals start at $92 SGD per night before taxes and fees

Verified guest reviews
Over 3,800 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
80 of Ponta do Sol holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ponta do Sol rentals

4.8 Average rating
Ponta do Sol stays are highly rated by guests – averaging 4.8 out of 5!
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- Porto Santo Beach
- Madeira Botanical Garden
- Praia do Porto do Seixal
- Casino da Madeira
- Monte Palace Tropical Garden
- Praia da Calheta
- Beach of Madalena do Mar
- Ponta do Sol Beach
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