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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Guest favourite

Condo in Caniço

4.86 out of 5 average rating, 153 reviews

Family friendly apartment swimming pool ocean view

A perfect family friendly apartment for who wants to spend a holiday with kids or friends in a wonderful island in Madeira which offers confortable climate all year long. Apartment is fully furnished and equipped with all the appliances that you need to spend your holidays. Amazing ocean view, perfect location to watch sunrise and sunset from the balcony. It is suitable for kids and infants, has high chairs from 0 to 5 years old, potty chair and a baby cot for the little ones, also a toy box.

Guest favourite

Home in Funchal

4.94 out of 5 average rating, 154 reviews

Place In The Sun

A beautiful and spacious house to enjoy your holiday in Madeira. From the private pool & BBQ terrace there are breathtaking ocean views over the bay of Funchal. The Botanical Gardens are 10 mins walk away and there is a bus stop 30 seconds away, taking 5mins to the centre. 3 mins walk away there is a restaurant, Sesamo bakery & mini supermarkets. The Aerobus stop is also a few minutes walk away. A fantastic view from the terrace to watch the world famous Madeira New Years Eve firework display.

Guest favourite

Home in Tabua

4.96 out of 5 average rating, 102 reviews

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!

Guest favourite

Home in Madeira

4.98 out of 5 average rating, 56 reviews

Panoramic View: Lux 3 bed w/ heated pool

Stunning modern villa with a private, heated infinity pool, 3 bedrooms and bathrooms, enjoying sea & mountain views. Located in one of the most sought-after areas with the best weather in the South West of Madeira island, the villa is unique in that it has a dedicated entertainment floor. Situated 5 mins away from Calheta Beach with its excellent restaurants on the marina & the same distance from Madalena do Mar beach. The house enjoys sun on the pool area from late morning until sunset.

Superhost

Apartment in Funchal

4.94 out of 5 average rating, 210 reviews

Atlantic Ocean View Apartment INFINITE POOL

The apartment is situated in front of the ocean, in the sunniest part of the city and has a infinity pool, jacuzzi and gym. You have direct access to Formosa beach from the pool area by foot. This is a comfortable full equipped apartment with A/C, coastal decoration with 2 double beds. The complex is close to public transport, Aerobus bus stop just outside the main gate, Parks, Formosa Beach, Natural Pools, Sea Promenade, Restaurants/ Cafes, Shopping Center, Cinema, Supermarket, etc..

Guest favourite

Apartment in Arco da Calheta

4.97 out of 5 average rating, 157 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.

Guest favourite

Cabin in Jardim do Mar

4.95 out of 5 average rating, 108 reviews

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.

Guest favourite

Home in Jardim do Mar, Calheta

4.93 out of 5 average rating, 40 reviews

Paradise by the sea | Jardim. Meu Amor!

A Stay Madeira apresenta o nosso novo projecto pessoal – JARDIM. MEU AMOR! Somos completamente apaixonados pelo Jardim do Mar! A nossa casa remonta o ano de 1937, quisemos dar-lhe uma nova vida, recuperamos e decoramos ao detalhe e com muito amor! A calma, o panorama e o som do oceano fazem deste lugar o sítio ideal para passar umas férias relaxantes na ilha da Madeira! Aguardamos pela sua visita! Até breve, Susana &Pedro

Superhost

Apartment in São Gonçalo

4.9 out of 5 average rating, 113 reviews

Charming View Apart. ✪free parking✪Amazing Sunsets

This apartment is located, on a hillside, in the high areas, east of Funchal. With the most enchanting panoramic view over the Atlantic Ocean, passing over Funchal, up to the mountains. Undoubtedly a privilege to see this wonderful landscape from the balcony of the apartment itself. Here I offer a quiet space providing moments of relaxation and well-being with the most unique sunsets ever seen.

Guest favourite

Villa in Ponta do Sol

4.98 out of 5 average rating, 118 reviews

Villa Miradouro da Baleia (Heated Pool optional)

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!

Superhost

Condo in Funchal

4.73 out of 5 average rating, 45 reviews

quinta falesia apartment

Apartment situated in a high class neighbourhood, fantastic swimmnig pool all year, perfect for a couple, or 4 friends. very quiet , fantastic sea view, even better from swimming pool area, shopping center infront of the building, rent a car services, bus stop at door step, all kind of restaurants, quiet neighbours, car parking.

Guest favourite

Apartment in São Gonçalo

4.94 out of 5 average rating, 17 reviews

Tucha's Apartment

Tuchas Apartement is an idyllic place where you are close to the city of Funchal but at the same time in peace and with the best view in the world!!! We are in a condominium, we are a newly renovated apartment, we have two bedrooms and a sofa bed with a shared pool! Book with us!