
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 $118 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).
FamilyLocationHospitality
4.95 out of 5 average rating, 114 reviews
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
LocationValueAccess
4.98 out of 5 average rating, 103 reviews
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.
LocationValuePool
4.99 out of 5 average rating, 225 reviews
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!
LocationFamilyParking
4.97 out of 5 average rating, 161 reviews
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.
ValueLocationIndoor spaces
4.95 out of 5 average rating, 144 reviews
A&M House II
A&M House II, the perfect place to enjoy your best vacation on Madeira Island. Located in a quiet area with a mild climate, it offers guests all the comfort they need to feel at home. Its stunning views make every evening unforgettable with its stunning sunsets. Come discover Madeira and enjoy the comfort that A&M House II has to offer.
FamilyValueBiking
5.0 out of 5 average rating, 51 reviews
Stylish 3BR Villa with Heated Pool & Views
Modern 3-bedroom villa in sunny Arco da Calheta with sea & mountain views. Enjoy a private heated pool, BBQ terrace, fast Wi-Fi, and secure garage. Walk to restaurants and cafés, 10 minutes by car to Calheta Beach and 30 minutes to Funchal. Ideal for couples, families, or groups — the perfect base to explore Madeira.
LocationFamilySolo travel
4.93 out of 5 average rating, 220 reviews
STONE HOUSE
This house is the symbiosis between the traditional past of the people and the island and the current and versatile reconstruction. It sleeps 4 people. Situated on the beach and village, it enjoys tranquility and good access to "Levadas", "veredas" and the Laurissilva Forest.
LocationValueHospitality
4.94 out of 5 average rating, 116 reviews
Casa do Penique ORGANIC
Casa do Penique Organic can be found on a dead end road, in a quiet Madeiran village, only 400 minutes from Funchal. It has been carefully restorated and now offers a spacious and relaxing space where you can enjoy an ocean view while sitting by the pond.
FamilyValueNearby
4.85 out of 5 average rating, 168 reviews
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.
FamilyLocationWi-Fi
4.95 out of 5 average rating, 43 reviews
Casa Diana Pool and Sea views
Casa Diana - a spacious modern cottage in the peaceful village of Loreto. A large sun terrace with swimming pool and amazing views over the Atlantic ocean offers a great place to relax and enjoy the sun.
LocationFamilyCleanliness
4.89 out of 5 average rating, 181 reviews
Casa Cro | Ocean View
Fully renovated house, where you can spend a fantastic, restful vacation. It has all the comfort to make you feel at home, and you can enjoy a beautiful swimming pool with a privileged view of the sea!
FamilyValueBathroom
4.94 out of 5 average rating, 201 reviewsPopular amenities for Calheta rentals with a pool
House rentals with a pool

Mango House
FamilyLocationCondition
4.93 out of 5 average rating, 118 reviews
Syso House
ValueLocationCondition
4.95 out of 5 average rating, 132 reviews
Relax Over The Sea -12391/AL
LocationFamilyIndoor spaces
4.98 out of 5 average rating, 103 reviews
Typical house above the sea
FamilyValueHospitality
4.99 out of 5 average rating, 199 reviews
Endless Blue House
FamilyLocationOutdoor spaces
4.97 out of 5 average rating, 115 reviews
Panoramic View: Lux 3 bed w/ heated pool
ValueLocationBarbecue
4.97 out of 5 average rating, 112 reviews
Villa Bisa Atlantic View ,heated pool
LocationFamilyComfort
4.97 out of 5 average rating, 158 reviews
Villa Rada, by Pausa Holiday Rentals
FamilyLocationKitchen
5.0 out of 5 average rating, 11 reviewsCondo rentals with a pool

Tropical Sunset D
LocationFamilyComfort
4.96 out of 5 average rating, 101 reviews
Renala II "With Pool" by PAUSA Holiday Rentals
ValueLocationKitchen
4.95 out of 5 average rating, 100 reviews
New dream luxury appartment in the Madeira Palace.
LocationFamilyBeach
4.99 out of 5 average rating, 145 reviews
Ocean View Apartment in Madeira
ValueFamilyAccess
4.89 out of 5 average rating, 132 reviews
Sunset Paradise, Funchal: sounds of the sea
ValueLocationComfort
4.94 out of 5 average rating, 100 reviews
Modern, lux comfort with Pool & Ocean view
LocationValueAccuracy
4.92 out of 5 average rating, 138 reviews
Charming Lido Flat I
FamilyValueCondition
4.92 out of 5 average rating, 146 reviews
Monumental Apartment
FamilyLocationOutdoor spaces
4.86 out of 5 average rating, 173 reviewsOther holiday rentals with a pool

Casa dos Reis
ValueLocationWalkability
5.0 out of 5 average rating, 29 reviews
Sunny Ocean View Villa - Calma
LocationFamilyPool
4.96 out of 5 average rating, 23 reviews
King´s View (Heated Pool and Sea View)
ValueFamilyBathroom
4.92 out of 5 average rating, 53 reviews
Casa Mar Azul 3
LocationFamilyPool
5.0 out of 5 average rating, 71 reviews
Villa Nicuma by Escape to Madeira
LocationDecorComfort
4.94 out of 5 average rating, 33 reviews
Casa Joaquim by Rent2u, Lda
LocationFamilyHot tub
5.0 out of 5 average rating, 13 reviews
Eco Fajã Villas - Deluxe - 60m above sea level
LocationNearbyDecor
5.0 out of 5 average rating, 4 reviews
Villa Panorama - Luxury Villa with Jacuzzi-Calheta
FamilyValueCheckout
4.96 out of 5 average rating, 94 reviewsDestinations to explore
- Funchal Holiday rentals
- Santa Cruz de Tenerife Holiday rentals
- Caniço Holiday rentals
- Arco da Calheta Holiday rentals
- Ribeira Brava Holiday rentals
- Madeira Island Holiday rentals
- Porto Santo Holiday rentals
- Machico Holiday rentals
- La Palma Holiday rentals
- Câmara de Lobos Holiday rentals
- Ponta do Sol Holiday rentals
- San Cristóbal de La Laguna Holiday rentals
- 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
- Blandy's Wine Lodge
- Madeira Whale Museum
- Cristo Rei
- Ponta do Pargo
- Santa Catarina Park
- Cascata Dos Anjos
- CR7 Museum
- Sé do Funchal
- Clube de Golf Santo da Serra





