
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 $101 AUD 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.

Ocean Dream • Luxury Apt with Large Terrace & Pool
Ocean Dream is a spacious, south-facing luxury apartment at Casa Shambhala, a brand-new residence (2026) in sunny Arco da Calheta, Madeira. Surrounded by banana fields and overlooking the Atlantic, it features stunning ocean views, a large private terrace, shared pool (only 3 apartments), private parking and a fully equipped kitchen - just a 5 minute drive to Calheta Beach and Marina, within easy reach of levadas, waterfalls, paragliding spots and Madeira’s most beautiful coastal villages.

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
Villa with a good view and plenty of sunshine throughout the day. The house is located in one of the best spots in the parish. Dispoe with two bedrooms, living room / kitchen and two bathrooms, with lot for 6 people. The house is located on top of a hill, which gives it an extraordinary view. Outside there is a barbecue, a large garden and a swimming pool. Absolute tranquillity. Come and spend a pleasant holiday at CASA SOL E VISTA. Contact Duarte Paulo

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). .

Villa Nicuma by Escape to Madeira
Relax comfortably with incredible views of the Atlantic Ocean. This luxury villa is just a short walk from restaurants, bars, and the center of Villa da Calheta and its marina. The beach is nearby, and the house offers a rooftop pool overlooking the sea and marina, where you can enjoy water activities. Come enjoy an unforgettable vacation where the sea, sun, and comfort come together to offer you a unique experience.

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.

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.

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.

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.
Popular amenities for Calheta rentals with a pool
House rentals with a pool

Casa do Penique ORGANIC

Stunning 3BR Villa | Ocean-View, Private Pool

MG House

Casa Cro | Ocean View

Pereira's Domus

Panoramic View: Lux 3 bed w/ 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

Luxury Big Apartment/Ocean view/Free Parking

Monumental Apartment

Whitehouse408 Sw.Pool & Pvt. Parking

New dream luxury appartment in the Madeira Palace.

Villa Elizabeth - The View 4
Other holiday rentals with a pool

Peak A Boo (Private Heated Pool & Private Parking)

Top View Calheta, villa with pool and jacuzzi

Villas Calhau da Lapa 10

Villa Acacia- Spectacular Ocean view & heated pool

Villa Panorama - Luxury Villa with Jacuzzi-Calheta

Unique Tropical Style Penthouse with a Dreamy View

Sunshine Villa & Opt. Heated Pool 150m above Ocean

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





