
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 $120 NZD per night before taxes and fees

Verified guest reviews
Over 6,520 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
150 of Calheta holiday rentals include Wi-Fi 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.

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 Sol e Vista
Moradia com boa vista e bom sol durante todo o dia. A casa está localizada num dos melhores locais da freguesia. Dispoe de dois quartos de dormir, sala / cozinha e duas casas de banho, com lotaçao para 6 pessoas. A casa esta situada no cimo de uma colina o que faz com que a casa tenha uma vista extraordinaria. No exterior tem um churrasco, um grande jardim e a piscina. Absoluta tranquilidade. Venha passar umas férias agradaveis na CASA SOL E VISTA. Contactar Duarte Paulo

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

Top View Calheta: Villa with Pool and Jacuzzi
Traga toda a família para esta soberba casa com piscina e jacuzzi exterior e com espaços bem generosos, muito espaço para se divertir. A casa fica situada em Estreito Da Calheta, com vista para o mar, muito perto de farmácia, supermercados, mercado, centro de saúde, os principais pontos turísticos, rabaçal, 25 fontes, risco......, varias levadas da Madeira, a praia de areia amarela, o aeroporto fica a 40 minutos de distância

Modern & New Studio w/ Pool & Oceanside View | G 🌟
Modern studio in the sunny and serene, sunny village of Jardim do Mar, south west of Madeira Island. Studio G features an open plan design with kitchenette, lounging area with TV (with Netflix), a cozy king sized bed, a spacious bathroom and a private south facing balcony with ocean and pool view. We provide free Wi-Fi and free parking (the property is a minute walk from the village's centre and the main free parking lot). .

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.

Casa Mariana by Rent2U, Ltd.
Old house, in a quiet area of Arco da Calheta, completely renovated, furnished and equipped with all kinds of appliances and utensils for everyday life. Great for families with kids, or couples who want to spend a few days relaxing, enjoying the sun and the wonderful views that surround the house.

Luxury Villa Pérola
Welcome to our exquisite cliffside villa, with unparalleled ocean views. This opulent sanctuary is a dream at sunrise and sunset. Escape to this haven of natural beauty and luxury for an unforgettable retreat. A unique and tranquil getaway.

In peaceful Prazeres | Qta Inácia Sunflower Studio
Set on the peaceful rolling hills below the village Prazeres, overlooking the sea, Quinta Inácia is a lovely new complex of apartments in Madeira with 3 Studios, the refurbished Old Cottage, and a lovely heated swimming pool.

Casa Cro | Ocean View
Casa totalmente recuperada, onde poderá passar umas fantásticas férias descansado. Possui todo o conforto para que se sinta em casa, podendo usufruir de uma bela piscina com vista privilegiada para o mar!
Popular amenities for Calheta rentals with a pool
House rentals with a pool

Tropical Garden 4

The Sunset Avenue w/infinity pool(optional heated)

Ladeira dos Zimbreiros Villa

Villas Calhau da Lapa 10

Panoramic View: Lux 3 bed w/ heated pool

Villa Bisa Atlantic View ,heated pool

Typical house above the sea

Bella Vista (Heated Pool & Private Parking)
Condo rentals with a pool

Ocean View Apartment in Madeira

Tropical Sunset D

Spectacular Ocean and Cliff views with Pool

Casa Mar Azul 3

Luxury Big Apartment/Ocean view/Free Parking

III - Savoy Monumentalis, By Pausa Holiday Rentals

Monumental Apartment

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

Villa Arco-Iris, a Home in Madeira

Tropical Honeymoon Suite

Paradise by the sea | Jardim. Meu Amor!

Stunning 3BR Villa | Ocean-View, Private Pool

Villa Nicuma by Escape to Madeira

Ocean Dream • Luxury Apt with Large Terrace & Pool

Casa das Vacas – Retreat House

Sunshine Villa & Opt. Heated Pool 150m above Ocean
Destinations to explore
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- Praia do Porto do Seixal
- Monte Palace Tropical Garden
- Madeira Botanical Garden
- Casino da Madeira
- Zona Velha
- Praia da Calheta
- Ponta do Sol Beach
- Porto Moniz Natural Swimming Pools
- Praia Machico
- Complexo Balnear do Lido
- Praia de Garajau
- Cabo Girão
- Pico Do Areeiroo
- PR 11 - Vereda dos Balcões
- Fish Market
- Casas Tipicas de Santana
- Madeira Whale Museum
- Sé do Funchal
- Ponta do Pargo
- Santa Catarina Park
- Funchal Cable Car
- Blandy's Wine Lodge
- Cristo Rei
- CR7 Museum





