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

Total holiday rentals
Explore 140 holiday rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta holiday rentals start at $97 AUD per night before taxes and fees

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Over 4,200 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
140 of Estreito da Calheta holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Estreito da Calheta rentals

4.8 Average rating
Estreito da Calheta stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Estreito da 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).

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.

Villa Rada, by Pausa Holiday Rentals
This stylish two-level villa features three bedrooms, each with its own private bathroom, plus an additional guest WC. The open-plan interior offers a bright, welcoming atmosphere with air conditioning and contemporary design. Outside, enjoy a private pool, barbecue area, comfortable sun loungers, and an outdoor dining area, all set against stunning sea and mountain views. Located in a peaceful area of the island, it’s the perfect place to relax and experience Madeira in comfort and style.

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.

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

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 - 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.

Marina View Apartment - Pool, Aircon & Ocean View
Welcome to Marina View Apartment! A fantastic 2 bedroom apartment set in a peaceful location of Calheta, the South Coast of the island where not only the sun shines almost every day but a fantastic location to explore the island. What truly makes this place special is the generous private outside space and infinity pool with spectacular views of the Atlantic ocean and Calheta Marina.

Syso House
House of modern architecture designed to offer a sense of freedom and connection with nature. You can relax in the pool designed to offer a sensational view of the ocean. This villa is located in a rural area, where you will have access to pharmacy, grocery stores with local products, post office and health center a few meters.

Relax Over The Sea -12391/AL
Beautiful spacious villa perched on the cliff top, stunning views of the Atlantic Ocean, its swimming pool with infinite plane over the ocean provides fantastic and relaxing moments for larger families in the sunniest located part of the island

Villa Papaya
An Outstanding Location, with a Fabulous View. Splash Pool and a Table to do meals outside. Unforgetable Sunset, with the sea and the Marina View! Villa Papaya Address: Rua Serra D’Água - Vereda do Morgadinho N. º 24 9370-076 Arco da Calheta
Popular amenities for Estreito da Calheta rentals with a pool
House rentals with a pool

STONE HOUSE

Panoramic View: Lux 3 bed w/ heated pool

Casa Cro | Ocean View

Typical house above the sea

Casa do Penique ORGANIC

Villa Bisa Atlantic View ,heated pool

Endless Blue House

A&M House II
Condo rentals with a pool

Vargem Mar Beach

Tropical Sunset D

Renala II "With Pool" by PAUSA Holiday Rentals

New dream luxury appartment in the Madeira Palace.

Ocean View Apartment in Madeira

Sunset Paradise, Funchal: sounds of the sea

Spectacular Ocean and Cliff views with Pool

Charming Lido Flat I
Other holiday rentals with a pool

Casa dos Reis

Villa with large pool and fantastic view

Casa Joaquim by Rent2u, Lda

King´s View (Heated Pool and Sea View)

Eco House @ Casas Da Vereda

Quinta Aurora - Heated, Private Pool & Ocean View

Grey Rock Villa

Sunny Ocean View Villa - Calma
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- Praia do Porto do Seixal
- Monte Palace Tropical Garden
- Zona Velha
- Praia da Calheta
- Madeira Botanical Garden
- Ponta do Sol Beach
- Casino da Madeira
- Porto Moniz Natural Swimming Pools
- Praia Machico
- Complexo Balnear do Lido
- Cabo Girão
- Praia de Garajau
- PR 11 - Vereda dos Balcões
- Casas Tipicas de Santana
- Fish Market
- Madeira Whale Museum
- Blandy's Wine Lodge
- Ponta do Pargo
- Cristo Rei
- Santa Catarina Park
- Cascata Dos Anjos
- CR7 Museum
- Sé do Funchal
- Clube de Golf Santo da Serra





