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Holiday rentals with a pool in Santana

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Santana

  • Total holiday rentals

    Explore 30 holiday rentals in Santana

  • Nightly prices starting at

    Santana holiday rentals start at £75 per night before taxes and fees

  • Verified guest reviews

    Over 420 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Santana holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Santana rentals

  • 4.5 Average rating

    Santana stays receive an average rating of 4.5 out of 5 from guests

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 unique swimming pool is partially embedded within rock formations, featuring crystal-clear water that reflects the bright blue sky above. Natural light filters through, creating a serene atmosphere in this inviting space.
Home in Campanario

Villas Calhau da Lapa 10

Welcome to Villa Calhau da Lapa 10, located in Campanário, 600 meters from the beach, where the splendor of the sea and mountains come together to create a truly captivating setting. This 19th century property was rebuilt over three years (2021 to 2024) by artists and craftsmen, giving it a unique identity, and was designed to provide maximum comfort and an exclusive lifestyle, offering an unparalleled residential experience. Located in an easily accessible location, this villa offers panoramic views of the sea and mountains. With a private, heated swimming pool, 12 meters long, 6 meters of which are excavated in the rock, giving it a unique identity and romanticism. The Villa offers 2 comfortable bedrooms, with flat-screen cable TV, air conditioning, fully equipped kitchen with stove, refrigerator, microwave, Nespresso coffee maker, washing machine and dryer, two bathrooms, outdoor barbecue free Wi-Fi and free parking. With space entirely dedicated to your well-being: swimming in the pool, relaxing in the garden or enjoying a barbecue are some of the privileged moments that Villa Calhau da Lapa 10 offers its guests.

4.98 out of 5 average rating, 55 reviews
Top guest favourite
A balcony offers a sweeping view of the sea and Paul do Mar, with a wrought iron railing framing the scene. The sunlight casts a warm glow over the landscape, creating a serene atmosphere. Lush greenery surrounds the area, enhancing the natural beauty.
Villa in Fajã da Ovelha

Quinta São Lourenço- Casa Palheiro | Sunset & Pool

Tourist tax included > no extra fees at arrival Free cancellation up to 5 days before your stay The « Quinta São Lourenço » is a traditional Madeiran property of 3 000 m² from the 19th century, renovated into independent houses. The Quinta is an ideal holiday destination and is well known for its dominant position on the Atlantic Ocean, its beautiful flower garden and its shared outdoor swimming pool. Let yourself be surprised by the majestic sunsets and take a break with the roar of the Ocean.

4.98 out of 5 average rating, 221 reviews
Guest favourite
Flat in Funchal

Madeira Oceanfront Retreat - Direct Beach Access

A new, exclusive,and sensory experience escape, suspended above the Atlantic, where ocean, cliffs and sunset come together in a premium oceanfront condominium with direct access to Praia Formosa. It offers breathtaking panoramic views and an atmosphere designed for pure well-being and disconnection. The sound of the waves fills the space, natural light flows all day and the sunset transforms the landscape every evening into a living postcard over the ocean and the dramatic cliffs of Cabo Girão.

5.0 out of 5 average rating, 7 reviews
Guest favourite
A private infinity pool is set against a backdrop of the ocean, surrounded by lush tropical plants. Comfortable seating, featuring blue cushions, faces the pool and ocean views, creating a relaxing outdoor space. The bright sky enhances the tranquil atmosphere.
Home in Funchal

Seafront Home in Old Town Funchal w Pool & Garden

Beachfront design home featured in Conde Nast Traveller w private pool & tropical garden in Old Town of Funchal. A stunning oasis just 5min walk to city center, beach & restaurants. Free street parking, fast internet & strong AC. 2 bedroom historic villa with 2 WC´s, living room & kitchen w sea views. Stylish interiors & lots of outside relaxing, sunbathing & dining area with BBQ. Tropical villa that feels like the countryside w amazing climate. Perfect base to explore Madeira´s hikes & beaches

4.94 out of 5 average rating, 117 reviews
Top guest favourite
Home in Fajã da Ovelha

Casa do Terrāço - Quinta Falcões Do Sol

Casa Terrãço is a restored stone house that combines the unique charm of a centuries-old structure with modern comfort. The house features an open floor plan on the first level with a fully equipped kitchen and living space that offers ocean views through a big glass door. The top floor contains a spacious bedroom that opens to a large private terrace, providing breathtaking views of the ocean. Outside you will have a private area with a fire pit and access to the shared heated saltwater pool.

4.94 out of 5 average rating, 69 reviews
Guest favourite
An outdoor dining area features a wooden table set with dishes and plants, surrounded by a few chairs. The rustic orange exterior of the adjacent building complements the lush greenery. The sea view can be seen in the background under an overcast sky.
Home in Arco da Calheta

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.

4.93 out of 5 average rating, 118 reviews
Top guest favourite
The image captures a scenic view of a coastal landscape featuring terracotta-roofed houses set against a backdrop of rugged mountains and a calm sea. Lush green trees frame the scene, enhancing the natural beauty of the environment.
Home in Porto da Cruz

Mateus House, "Duplex", Town Center, Beach.

The perfect combination between mountains proximity to the sea within a Relaxed atmosphere. A Private solarium area, sun loungers among other facilities. Two bathrooms, Wi-Fi, several board games, cot, 2 electric scooters. You can be Extra sure of a Genuine Hospitality. Exclusive and personalized service of this property, guaranteeing a close attention to Every Detail. A small Private Garden available is waiting for you. Walking Sticks, several Bodyboards and Surf boards.

4.88 out of 5 average rating, 81 reviews
Guest favourite
A yurt is positioned amidst vibrant yellow flowers, set against a backdrop of lush greenery. The coastline and a winding road are visible in the distance, with the ocean meeting a partly cloudy sky, creating a serene and natural landscape.
Yurt in Ponta do Sol

Mango Yurt ~Eco-Glamping 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 Ba,r and stunning views of the sea and waterfall. 💧🌿 More pictures and vibes: @cantodasfontes

4.97 out of 5 average rating, 472 reviews
Guest favourite
An indoor swimming pool is featured, surrounded by large windows that offer natural light and views of the garden. The pool is filled with clear blue water, and a staircase leads into it. A dining area with tables is positioned nearby.
Home in Porto da Cruz

House pc / piscina interior privada

O House Pc encontra-se na tranquila Vila do Porto da Cruz, Nordeste da Ilha da Madeira, localização privilegiada sobre o oceano Atlântico, banhada pela Corrente do Golfo, que garante verões amenos e invernos suaves. Envolvida pelas montanhas e mar, com a simpatia da sua população, torna se um local ideal para repousar, sintonizar com natureza, saborear a gastronomia local ou aventurar se em desportos náuticos e radicais.

4.86 out of 5 average rating, 140 reviews
Guest favourite
A vibrant pink house stands beside a private swimming pool, surrounded by paved flooring and sun loungers. Lush greenery and mountains create a scenic backdrop, highlighting the tranquil rural setting. Clear blue skies add brightness to the inviting outdoor space.
Home in Santana

A Casa do Lagar - Country Villa

Private pool Situated in a tranquil area with year-round pleasant weather, offering spectacular views of the sea and mountains. The beach and mountains are just a 5-minute drive away, or guests can opt for scenic walks along nearby trails. Only 25 minutes from the airport and 35 minutes from Funchal. The accommodation accommodates 8 guests with 2 additional persons in extra beds, please contact us.

4.86 out of 5 average rating, 108 reviews
Top guest favourite
An infinity pool stretches over a wooden deck, with views of the expansive Atlantic Ocean and dramatic cliffs. Sunlight reflects off the water's surface, enhancing the serene atmosphere. Surrounding greenery complements the natural setting, inviting relaxation and contemplation.
Flat in Paul do Mar

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.

4.99 out of 5 average rating, 225 reviews
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.
Guest house in Machico

Private Pool House• 2 Suites• Near Airport & Beach

Enjoy a relaxing stay in this elegant and private Pool House, featuring two en-suite bedrooms, a kitchenette, a swimming pool, a sunny terrace and a small lawned garden. Reserved exclusively for one booking at a time, it offers complete privacy. Just 500 m from Machico’s centre, sandy beach, restaurants and shops, 5 minutes from Madeira Airport and 10 minutes from Santo da Serra Golf Course.

4.99 out of 5 average rating, 112 reviews

Popular amenities for Santana rentals with a pool