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Vacation rentals with a pool in Madeira Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Madeira Island

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)!

Home in Ribeira Brava

4.87 out of 5 average rating, 115 reviews

Unique House - Pool, Terrace & Amazing View

Casa Das Pedras is a unique property located on the cliff side with amazing sea views, a swimming pool cut into the rock side with a waterfall and lights; a bathroom in a cave; a large terrace to relax on; and in those milder evenings, a fireplace to cozy up to. As well as the three double bedrooms, we have an attic games room where mattresses can be organised for kids. Located close to Lavada Do Norte, you can take great walks during the day and chill out on the terrace in the evening.

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 Ponta Do Sol

4.99 out of 5 average rating, 151 reviews

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. With no neighbors close by, you will find here the heaven you are seeking. 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

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.

Cottage in Madeira

4.95 out of 5 average rating, 135 reviews

Cork House By Fernandes’s Cottage - Madeira island

A modern and cosy apartment, close to the mountains and the sea, in the picturesque village of Ponta Delgada in Madeira Island. Perfect for a relaxing holiday or for working peacefully outdoors, ready to accommodate a family of 4 or two couples. Ideal location to explore the North Coast of the island but also at a short drive from the South Coast. On your return, at the end of the day, the property's refreshing swimming pool is waiting to help you recover.

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.

Guest suite in Ponta do Sol

4.9 out of 5 average rating, 152 reviews

A View For You

É um alojamento com uma fantástica vista para o mar da nossa paradisíaca Ilha da Madeira! Muito agradável, com todas as comodidades, localizado numa zona privilegiada da ilha, com clima temperado todo o ano, tudo para ter umas férias maravilhosas e inesquecíveis! Permite o uso de piscina de sal, temperada, que pode ser partilhada com outros hóspedes. Todos os hóspedes são bem vindos! Sejam felizes e divirtam-se nas vossas férias! :-)

Home in Ribeira Brava

4.97 out of 5 average rating, 109 reviews

Casa Velha D. Fernando

Casa Velha D. Fernando is an apartment that offers a magnificent view from the terrace to the Ocean. It is a 15-minute drive from the city of Funchal and 30 minutes from the airport. It has all the facilities such as WiFi, full bathroom, TV, microwave and toaster essential for a fantastic and relaxing holiday. a barbecue, sun loungers and an outdoor dining area. An excellent starting point for the discovery of the island. Free wifi.

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.

Home in Funchal

4.87 out of 5 average rating, 237 reviews

Your home away from home in Madeira.

Bem vindo ao paraíso na Madeira! Relaxe nesta casa deslumbrante e totalmente equipada com 2 quatros acolhedores, uma grande varanda, área de churrasco e piscina. Esperamos por ti! Welcome to paradise in Madeira! Immerse yourself in pure relaxation and breathtaking views in our home. With 2 comfy bedrooms, one big balcony, barbecue area and pool. We cannot wait to see you!

Vacation rentals for every style

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Popular amenities for Madeira Island rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Gaula

4.86 out of 5 average rating, 64 reviews

Fazendinha by Real Vision

Home in Estreito da Calheta

4.86 out of 5 average rating, 122 reviews

Casa do Penique ORGANIC

Home in Arco da Calheta

5 out of 5 average rating, 11 reviews

Tropical Garden 4

Home in Santa Cruz

4.93 out of 5 average rating, 235 reviews

Casa do Cristo Rei

Home in Funchal

4.84 out of 5 average rating, 123 reviews

OceanView Villa 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 Funchal

4.99 out of 5 average rating, 134 reviews

Casa dos Francelhos, the charming house of Funchal

Home in Calheta

4.95 out of 5 average rating, 165 reviews

Casa Cro | Ocean View

Condo rentals with a pool

Condo in Funchal

4.9 out of 5 average rating, 82 reviews

Ocean View Madeira Apartment

Condo in São Gonçalo

4.92 out of 5 average rating, 50 reviews

Sea and Mountain View

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 Funchal

4.87 out of 5 average rating, 159 reviews

My Cozy Spot

Condo in Funchal

4.85 out of 5 average rating, 118 reviews

Varandas do Funchal Apartment

Destinations to explore