
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 $128 SGD 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.

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
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
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
Villa Nóbrega
Discover the perfect getaway on Madeira Island! A luxury villa, designed to offer comfort and an unforgettable experience. With a prime location and incredible views of the city and the sea, it is ideal for sunrise lovers. The villa has a suite and two large bedrooms, all with air conditioning and a private balcony. It has an integrated living room and kitchen, infinity pool, garden, barbecue area and private garage. A perfect place to relax and create unique memories.
5.0 out of 5 average rating, 57 reviews
Ocean View Villa Madeira
Located in an exclusive and privileged location you can enjoy simultaneously the advantages of privacy along with the proximity to the the capital's city centre. Merely 10 minutes away from the historical centre and the gorgeous marina and promenade that you can see while relaxing in the pool. A breathtaking ocean view and mountainous surroundings make this a very special and unique place to stay. You will find out why we are called the "Pearl Of The Atlantic".
4.85 out of 5 average rating, 162 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.
4.93 out of 5 average rating, 221 reviews
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, 107 reviews
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.
4.99 out of 5 average rating, 225 reviews
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
House pc / private indoor pool
House Pc is located in the quiet Vila do Porto da Cruz, northeast of Madeira Island, a privileged location on the Atlantic Ocean, bathed by the Gulf Stream, which guarantees mild summers and mild winters. Surrounded by mountains and the sea, with the friendliness of its people, it is an ideal place to rest, tune in to nature, taste the local cuisine or venture into water and extreme sports.
4.86 out of 5 average rating, 140 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
4.99 out of 5 average rating, 200 reviews
Gilda's Studio
This stylish accommodation is perfect for couples traveling. In an area where you can contemplate the sea and the mountains and enjoy a magnificent sunrise. It is located 30 km from downtown Funchal, 13 km from Madeira airport and 1 km from the village of Porto da Cruz.
5.0 out of 5 average rating, 25 reviewsPopular amenities for Santana rentals with a pool
House rentals with a pool

Lovely house with spectacular views over Funchal
4.81 out of 5 average rating, 188 reviews
Villa Cary
4.98 out of 5 average rating, 109 reviews
Rochinha house with pool and fabulous view
4.84 out of 5 average rating, 162 reviews
Old Wine Villa
4.95 out of 5 average rating, 150 reviews
Casa Velha D. Fernando (Old House D. Fernando)
4.98 out of 5 average rating, 166 reviews
Syso House
4.95 out of 5 average rating, 132 reviews
Panoramic View: Lux 3 bed w/ heated pool
4.97 out of 5 average rating, 113 reviews
Villa Pérola | Pool & Panoramic Ocean View
4.95 out of 5 average rating, 43 reviewsApartment rentals with a pool

Spectacular Ocean and Cliff views with Pool
4.85 out of 5 average rating, 126 reviews
Tropical Sunset D
4.96 out of 5 average rating, 101 reviews
Renala II "With Pool" by PAUSA Holiday Rentals
4.95 out of 5 average rating, 102 reviews
New dream luxury appartment in the Madeira Palace.
4.99 out of 5 average rating, 146 reviews
Charming Lido Flat I
4.93 out of 5 average rating, 147 reviews
Monumental Apartment
4.86 out of 5 average rating, 173 reviews
Sunset Paradise, Funchal: sounds of the sea
4.94 out of 5 average rating, 102 reviews
Vargem Mar Beach
4.92 out of 5 average rating, 132 reviewsOther holiday rentals with a pool

Oceanfront | Direct Beach Elevator | Infinity Pool
4.98 out of 5 average rating, 44 reviews
Villa Ricardo - A Charming Villa
4.7 out of 5 average rating, 33 reviews
Incredible views, saltwater pool, and BBQ
4.85 out of 5 average rating, 20 reviews
Quinta das Colmeias - The Cottage
4.75 out of 5 average rating, 142 reviews
The Dock House
4.78 out of 5 average rating, 208 reviews
Quinta Marefe - On the stunning west coast
5.0 out of 5 average rating, 39 reviews
Penha D Águia Villa
4.81 out of 5 average rating, 16 reviews
The Blue Sanctuary Relax Pad
4.8 out of 5 average rating, 40 reviewsDestinations to explore
- Funchal Holiday rentals
- Caniço Holiday rentals
- Arco da Calheta Holiday rentals
- Ribeira Brava Holiday rentals
- Madeira Island Holiday rentals
- Porto Santo Holiday rentals
- Machico Holiday rentals
- La Palma Holiday rentals
- Câmara de Lobos Holiday rentals
- Ponta do Sol Holiday rentals
- São Vicente Holiday rentals
- Santa Cruz de La Palma Holiday rentals
- Porto Santo Island
- Praia do Porto do Seixal
- Zona Velha
- Monte Palace Tropical Garden
- Praia da Calheta
- Madeira Botanical Garden
- Ponta do Sol Beach
- Casino da Madeira
- Porto Moniz Natural Swimming Pools
- Praia Machico
- Cabo Girão
- Praia de Garajau
- Complexo Balnear do Lido
- PR 11 - Vereda dos Balcões
- Casas Tipicas de Santana
- Fish Market
- Cristo Rei
- Blandy's Wine Lodge
- Madeira Whale Museum
- Ponta do Pargo
- Santa Catarina Park
- Cascata Dos Anjos
- CR7 Museum
- Sé do Funchal





