
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 $90 SGD 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 & 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
140 of Estreito da Calheta holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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.

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).

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.

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.

Vila Aguarelas with pool by Stay Madeira Island
A unique stay in an elegant and refined accommodation, modern and comfortable, thoughtfully designed just for you! Vila Aguarelas offers 3 suites, each featuring a double bed and private bathroom. In an open-plan layout, there’s a living room with a dining table and a fully equipped kitchen. You can also enjoy the incredible pool (optional heating upon request; additional cost of €35 per night, minimum stay required—please notify at the time of booking or at least one week prior to arrival).

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.

Infinite Ocean View Villa 20m above Ocean & Beach
Naturalis Villas, one of the best platforms for Madeira Villa Holidays Rental presents: Villa Infinity ထ is a true paradise villa positioned on a small cliff 20m above a wild beach, surrounded by banana plantations and a large 10 x 5 metre optionally heated infinity pool offering 180 degree ocean views and sunsets all year round. Completely renovated in a contemporary style with rustic features, it has central air conditioning system as well as fiber optics Wi-Fi internet connection.

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

Eco Fajã Villas - Deluxe - 60m above sea level
High above the coastline is a private sanctuary where luxury meets nature. With sweeping panoramic sea views, a larger heated infinity pool, and an expansive garden, this villa is designed for those who seek space, tranquility, and exclusivity. Its sleek open-plan interiors, flooded with natural light, blend seamlessly with the outdoors, creating an effortless flow between modern comfort and Madeira’s breathtaking landscape.

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.

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

Villa Arco-Iris, a Home in Madeira
Villa Arco-iris is a spacious, modern house with a wide sea view, ideal for families and groups of up to four people. It is located in a sunny and quiet area in Calheta, in the southwestern part of Madeira, which has the most favourable climate on the island.<br>This villa stands out for its modern architecture, air conditioning and various amenities and details for comfort and leisure.
Popular amenities for Estreito da Calheta rentals with a pool
House rentals with a pool

Syso House

Mango House

Panoramic View: Lux 3 bed w/ heated pool

Casa da Cascata B&B | Levada Houses

Seafront Home in Old Town Funchal w Pool & Garden

Relax Over The Sea -12391/AL

Old Wine Villa

Villa Vera Garajau - Madeira Island
Apartment rentals with a pool

Vargem Mar Beach

Tropical Sunset D

Charming Lido Flat II

New dream luxury appartment in the Madeira Palace.

Ocean View Apartment in Madeira

Modern, lux comfort with Pool & Ocean view

Whitehouse408 Sw.Pool & Pvt. Parking

Luxury Big Apartment/Ocean view/Free Parking
Other holiday rentals with a pool

Villa Nicuma by Escape to Madeira

Villa Panorama - Luxury Villa with Jacuzzi-Calheta

A&M House II

Villa with large pool and fantastic view

Grey Rock Villa

Sweet Paradise

Casa Joaquim by Rent2u, Lda

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





