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Holiday rentals with a pool in Santana

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Santana

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

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Guest favourite
A large heated saltwater pool is set against a backdrop of ocean and mountain views, framed by modern glass doors. Sunlight reflects off the water, enhancing the tranquil atmosphere. Spacious terraces surrounding the pool provide ample space for relaxation.
Villa in Arco da Calheta
4.96 out of 5 average rating, 103 reviews

Villa Lara, sea views, heated Pool A/C

Villa Lara is a fabulous modern single story three bedroom villa in the sought after area of Arco da Calheta. Lovely ocean and mountains views, sun terraces with a large private heated salt water pool and space for outside dining. There is an open plan fully fitted kitchen with a dining table for formal dining, leading to a comfortable sitting area with television with sliding doors leading outside. Facilities include aircon, heating, WIFI and parking. Approx. 10 minutes to Calheta beach. Fabulous spacious, light and modern 3 bedroom villa thoughtfully designed to maximize sun exposure and privacy. Fully fitted kitchen with all the required equipment to make you feel like you're at home. Large master bedroom with luxurious en-suite bathroom. Hot and cold air conditioning throughout, large heated swimming pool with ample sun terraces and garden area for relaxing or for children to run around. Alojamento Local License Number: 114112/AL We are at your disposal to help or answer your questions. We're contactable at any time via our mobile or by email. We will do our very best so you have a wonderful stay! Villa Lara is located centrally in Arco da Calheta with access to local amenities including various supermarkets, cafes, bars, restaurants and a pharmacy. Approx 10 minutes drive from the Villa and you'll be at Calheta Beach where you can enjoy the golden sand, several restaurants and book whale and dolphin watching tours. Villa Lara is ideal for couples, solo adventurers, families (with kids (cot & highchair can be provided)), and big groups. Villa Lara is set in a peaceful location ideal for walking the levadas (unmissable walks in Calheta include Paul da Serra, Rabacal (to Risco Waterall & 25 Fontes), Levada Nova and the Prazeres to Paul do Mar walk) and is close to a bus route. The property is approximately 30 minutes drive to Funchal and 45 minutes from the airport. A car is recommended so you can explore the island at your convenience. If you wish to book a private transfer with our local partners, please contact us in advance (which will be cheaper than taking a taxi direct from the airport).

Guest favourite
The image captures a wooden-roofed structure situated beside a calm sea, with expansive views of the coastline and towering rocky cliffs under a clear blue sky. The serene waters glisten in the sunlight, providing a striking contrast to the natural landscape.
Place to stay in Jardim do Mar
4.95 out of 5 average rating, 278 reviews

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.

Guest favourite
A private terrace is seen adorned with a round dining table and two wooden chairs, overlooking the scenic Funchal harbor. Lush greenery frames the viewpoint, while the soft glow of sunset fills the sky, enhancing the relaxed atmosphere.
Apartment in Funchal
4.93 out of 5 average rating, 128 reviews

Painters Cottage Pool & Ocean View balcony Funchal

Walk to the beach & Funchal city center. Fantastic seaview 1 bedroom apartment in an authentic part of old Funchal with swimming pool, garden, BBQ & private terrace. Fast Internet & street parking. Enjoy the large balcony all year with warm climate & views of the harbour. Charming fully equipped flat set in a heritage property with beautiful interior design & a full kitchen. Perfect countryside feel base to live like a local surrounded by nature & explore Madeiras hikes, food & ocean in style

Top Guest favourite
A private pool area features a serene turquoise pool surrounded by wooden decking. Lounge chairs are positioned for relaxation, and vibrant greenery enhances the outdoor space. The backdrop includes modern glass doors, allowing for a seamless connection to the interior. Sunlight brightens the scene under a clear blue sky.
Guesthouse in Machico
4.99 out of 5 average rating, 100 reviews

Pool House, Like a Private Boutique Hotel

Composto por 2 suites e 1 kitchenette à beira da piscina com um agradável solário e um pequeno jardim com relva. O espaço é privado e disponibilizado apenas para um cliente de cada vez. Decoração elegante com pequenos detalhes para umas férias de sonho para disfrutar ao máximo do espaço exterior. Localizado a 500 metros do centro de Machico (praia de areia, restaurantes, supermercados e transportes públicos), a 5 minutos (3,2 km) do aeroporto e 10 minutos (7 km) do Golfe do Santo da Serra.

Superhost
Home in Ribeira Brava
5 out of 5 average rating, 4 reviews

Elegance By The Sea

Boasting 550 square meters, this stunning seaside house is the perfect location from which to enjoy everything Madeira has to offer. Located less than 5 minutes to multiple beaches, restaurants and shops and less than 15 minutes to some of the highest rated hikes on the island, Elegance is the perfect Madeira basecamp. The home's heated salt water pool, multiple terraces, custom sauna, ping pong, foosball tables and 85" QLED Samsung/Sonos combo make staying put a wonderful option.

Top Guest favourite
A secluded orange tent is positioned against a stunning sunset over the ocean. Vibrant colors fill the sky, with clouds gently illuminated. Lush greenery surrounds the tent, providing a sense of intimacy with nature in a tranquil, elevated setting.
Yurt in Ponta do Sol
4.97 out of 5 average rating, 659 reviews

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

Top Guest favourite
Home in Ribeira Brava
4.96 out of 5 average rating, 185 reviews

Casa Avó Augusta Cayenne

Casa Avó Augusta Hera is part of a 2-bedroom house, in stone, about 100 years old and with a stunning view of the sea. It is located 1.5 km from Ribeira Brava, in a rural area where it is possible to hear the sound of animals and sometimes that of agricultural work. The location is recommended for guests who have a car or who have no problem with local bus schedules. An excellent starting point for discovering the island. It is ideal for a relaxing couple's trip

Superhost
An outdoor dining area features a round table set with plates and a vibrant arrangement of fresh fruits. In the background, the infinity pool reflects the expansive sea views, with a serene landscape of greenery and clouds under a sunny sky.
Villa in Estreito da Calheta
4.9 out of 5 average rating, 10 reviews

Cliff-top villa, panoramic sea-views | Cliffscape

With outstanding panoramic sea-views and offering privacy and seclusion, surrounded by tranquil countryside, Cliffscape is a superb quality air-conditioned villa with heated pool that fully lives up to its name, with the great advantage that it is located in the sunniest area of Madeira and only 300m from the nearest facilities. Located at the end of its own driveway and perched on the cliff top, this contemporary villa is designed to embrace the superb views.

Guest favourite
A well-lit bedroom features a spacious bed adorned with decorative pillows. Large windows provide natural light and a view of palm trees and distant water, while a wooden ladder leans against the wall. Two rolled towels are neatly arranged on the bed.
Cottage in Ponta Delgada
4.94 out of 5 average rating, 190 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.

Top Guest favourite
An outdoor patio area features a wooden dining table accompanied by a comfortable hammock. Lush greenery frames the space, with ocean views visible in the background beneath a clear blue sky. The structural cover offers shade while maintaining a breezy atmosphere.
Apartment in Paul do Mar
5 out of 5 average rating, 228 reviews

Meu Pé de Cacau - Acerola Studio 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 handcrafted in basalt stone.

Top Guest favourite
The image captures a view of Casa Nambebe, with a terracotta roof and surrounded by lush banana trees. An inviting infinity pool reflects the blue ocean, while the rugged coastline and greenery enhance the tranquil setting. The house is positioned on a hillside overlooking the sea.
Home in Canhas
4.99 out of 5 average rating, 186 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. 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

Guest favourite
A quaint two-story house is nestled among lush greenery, featuring a warm white facade and wooden window shutters. A sloping tiled roof and a shaded porch are visible, surrounded by vibrant plants and trees that enhance its secluded charm.
Home in São Gonçalo
4.82 out of 5 average rating, 175 reviews

Lovely house with spectacular views over Funchal

The Stone House is set at the top of our estate with its own garden and pool. It sleeps six and has a spacious kitchen and living room with log-burner. Secluded but 15 mins' drive from Funchal - a perfect base from which to explore the island. Together with the other houses on this unique estate it can cater for a group of friends or family.

Popular amenities for Santana rentals with a pool

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