
Holiday rentals with a pool in Calheta
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Calheta

Total holiday rentals
Explore 150 holiday rentals in Calheta

Nightly prices starting at
Calheta holiday rentals start at $89 SGD per night before taxes and fees

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Over 6,520 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
150 of Calheta holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Calheta rentals

4.9 Average rating
Calheta stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with a pool in Calheta
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

NEW Quinta da Luz - By Your Madeira Rentals
🌿 Quinta da Luz – A Sustainable Retreat Above the Atlantic 🌊 Welcome to **Quinta da Luz** – a special place for travelers who want to experience Madeira authentically, consciously, and surrounded by nature. Perched above the Atlantic Ocean, Quinta da Luz combines modern architecture, privacy, and comfort with a deep respect for the island's natural beauty and resources. More than just a holiday villa, it is a peaceful retreat designed for guests who value tranquility, breathtaking views, and a slower, more mindful way of living. ☀️ Wake up to panoramic ocean views, enjoy breakfast on the terrace, and spend your days immersed in Madeira's spectacular landscapes. Whether you're hiking the famous levadas, exploring hidden corners of the island, or simply unwinding with a book overlooking the sea, Quinta da Luz offers the perfect setting to reconnect and recharge. 🏡 The Space The villa comfortably accommodates up to four guests and features: ✨ Two bedrooms with king-size beds ✨ Two modern bathrooms with walk-in showers ✨ Spacious living area with floor-to-ceiling views ✨ Fully equipped open-plan kitchen and dining area ✨ High-speed Wi-Fi ✨ Private parking ✨ Baby cot available upon request 🌱 A Sustainable Philosophy At Quinta da Luz, sustainability is not just a feature, it's part of the experience. ☀️ Solar energy helps power the property 🍋 Seasonal fruits and vegetables grow in our garden ♻️ Composting and responsible resource management are part of daily life 🌿 The surrounding landscape has been designed to preserve Madeira's natural character Our goal is simple: to offer a comfortable and memorable stay while respecting the beauty and resources of this extraordinary island. 💙 The Infinity Pool One of the highlights of Quinta da Luz is the infinity pool overlooking the Atlantic Ocean. 🌞 In keeping with our sustainability philosophy, the pool is **not artificially heated**. Instead, it is naturally warmed by Madeira's sunshine, meaning water temperatures vary throughout the year depending on the season and weather conditions. We believe this creates a more authentic connection to the island while helping reduce energy consumption and environmental impact. 🌅 Why Guests Love Quinta da Luz ✔️ Spectacular panoramic ocean views ✔️ Peaceful and private location ✔️ Contemporary architecture and premium comfort ✔️ Sustainable living concept ✔️ Close connection to nature ✔️ Stunning sunsets from the terrace ✔️ Perfect for couples, remote workers, and nature lovers ✨ If you're looking for more than just a holiday home, if you're looking for a place where comfort, sustainability, and Madeira's natural beauty come together, Quinta da Luz is ready to welcome you. We look forward to sharing this special corner of Madeira with you. 💙🌿

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).

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.

Stunning 3BR Villa | Ocean-View, Private Pool
Atlantic View by Costa Living – a peaceful and spacious ocean-view villa in Arco da Calheta. This freshly renovated and newly furnished 3-bedroom home (sleeps 9) features a private pool, panoramic Atlantic and mountain views, balcony, and modern open-plan living. Enjoy fast Wi-Fi, Smart TV, fully equipped kitchen, laundry and private garage. Set among nature and hiking trails, just minutes from Calheta Beach, Madalena do Mar Beach, and cafés. Perfect for families and friends. Car required.

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.

Casa Miradouro Loft - Pool by Stay Madeira Island
Stay Madeira Island presents Casa do Miradouro Loft. The ideal place to rest, relax, forget the routine and stress, all in one space! The accommodation has been prepared to offer you the perfect stay on Madeira Island. It is located on the southern coast of the island, in Ribeira Brava. This serene and spacious space is waiting for you! [Pool heating available upon request; extra cost of €25 per night; minimum stay (requested upon booking or up to one week prior to arrival)].

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

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.

CASA SOL E VISTA 2
Casa Sol e Vista 2 is located in one of the best locations in the parish, next to house no. 1. It has 2 bedrooms, a living room/kitchen and 3 bathrooms, accommodating 6 people. The house is located on top of a hill, which gives the house an extraordinary view. Outside, there is a barbecue, a large garden and a swimming pool. Absolute tranquility. Come spend a few pleasant days at Casa Sol e Vista 2. Contact Duarte Paulo

Meu Pé de Cacau - Mango Studio in Paúl do Mar
Meu Pé de Cacau is a tropical fruit garden and island retreat 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.

☀️ Bright & Spacious w/ Pool & Oceanside View :D
Modern studio in the sunny and serene coastal village of Jardim do Mar, south west of Madeira Island. Studio D features an open plan design with kitchenette, lounging area, TV (with Netflix), a cozy queen size bed, a spacious bathroom with washing machine and a private, south facing balcony with ocean and pool view (24° to 26° Celsius). Guests have full access to the garden and heated saltwater pool.

Villa Miradouro da Baleia by PAUSA Holiday Rentals
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!
Popular amenities for Calheta rentals with a pool
House rentals with a pool

Mango House

Syso House

STONE HOUSE

Relax Over The Sea -12391/AL

Villa Bisa Atlantic View ,heated pool

Villa Vera Garajau - Madeira Island

Casa Cro | Ocean View

Endless Blue House
Apartment rentals with a pool

Vargem Mar Beach

Tropical Sunset D

Charming Lido Flat II

Ocean View Apartment in Madeira

Modern, lux comfort with Pool & Ocean view

New dream luxury appartment in the Madeira Palace.

Monumental Apartment

Whitehouse408 Sw.Pool & Pvt. Parking
Other holiday rentals with a pool

Casa Joaquim by Rent2u, Lda

King´s View (Heated Pool and Sea View)

Premium villa, panoramic sea-view | Calheta Pearl

Villa with large pool and fantastic view

Villa Panorama - Luxury Villa with Jacuzzi-Calheta

Villa Arco-Iris, a Home in Madeira

Pereira's Domus

Eco Fajã Villas - Retreat - 60m above sea level
Destinations to explore
- Funchal Holiday rentals
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- Arco da Calheta Holiday rentals
- Ribeira Brava Holiday rentals
- Madeira Island Holiday rentals
- Porto Santo Holiday rentals
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- Ponta do Sol Holiday rentals
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- Praia do Porto do Seixal
- Monte Palace Tropical Garden
- Zona Velha
- Madeira Botanical Garden
- Praia da Calheta
- Ponta do Sol Beach
- Casino da Madeira
- Porto Moniz Natural Swimming Pools
- Praia Machico
- Complexo Balnear do Lido
- Praia de Garajau
- Cabo Girão
- Pico Do Areeiroo
- PR 11 - Vereda dos Balcões
- Casas Tipicas de Santana
- Fish Market
- Madeira Whale Museum
- Sé do Funchal
- Blandy's Wine Lodge
- Santa Catarina Park
- Ponta do Pargo
- Funchal Cable Car
- Cristo Rei
- CR7 Museum





