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

Total vacation rentals
Explore 150 vacation rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta vacation rentals start at G$6,263 GYD per night before taxes and fees

Verified guest reviews
Over 4,120 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
150 of Estreito da Calheta vacation rentals include wi-fi 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).

Quinta São Lourenço - Casa Lagar | Sunset & Pool
Tourist tax included > no extra fees at arrival Free cancellation up to 5 days before your stay The « Quinta São Lourenço » is a traditional Madeiran property of 3 000 m² from the 19th century, renovated into independent houses. The Quinta is an ideal holiday destination and is well known for its dominant position on the Atlantic Ocean, its beautiful flower garden and its shared outdoor swimming pool. Let yourself be surprised by the majestic sunsets and take a break with the roar of the Ocean.

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.

Panoramic View: Lux 3 bed w/ heated pool
Stunning modern villa with a private, heated infinity pool, 3 bedrooms and bathrooms, enjoying sea & mountain views. Located in one of the most sought-after areas with the best weather in the South West of Madeira island, the villa is unique in that it has a dedicated entertainment floor. Situated 5 mins away from Calheta Beach with its excellent restaurants on the marina & the same distance from Madalena do Mar beach. The house enjoys sun on the pool area from late morning until sunset.

Sweet Paradise
Um paraíso no coração da Zona Oeste da Madeira orientado a sul e com um pôr do sol fantástico. Zona residencial calma e com bons acessos. A 5min da praia, comércio e restaurantes e com uma ótima localização para explorar a ilha. Uma casa moderna com piscina de água salgada e aquecida (mediante pagamento), boas áreas, churrasqueira, zona de solário, jardim com ervas aromáticas, ginásio e estacionamento. Toda a casa é climatizada e com uma cozinha equipada para celebrar ótimos momentos.

Papaia Yurt ~ EcoGlamping 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 Bar, and stunning views of the sea and waterfall. 💧🌿 More pictures and vibes: @cantodasfontes

King´s Paradise (Heated Pool and Sea View)
King´s Paradise is in a peaceful location, perfect for family-friendly holidays. It is the best choice for those that wish to experience a little of Madeira tradition, tranquillity and privacy, and easy access to the mountains. Ideally located for a lovely holiday surrounded by the beautiful Madeira countryside. Nearby: 5 minutes by car is the Vila da Calheta, with its man-made golden beaches, beautiful marina and a good choice of bars and restaurants.

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.

The Rock Villas
The Rock Villas proposes 3 bedrooms for up to 6 guests, and great facilities such as its private heated swimming pools and other luxurious pieces of equipment. The 2 recent constructions blend harmoniously in the cliffy landscape while offering large views over the Atlantic ocean: a peaceful and stylish getaway on the South West coast of the island of Madeira.

Peak A Boo (Private Heated Pool & Private Parking)
Take it easy at this unique and tranquil getaway with breathtaking views. The interior design with large sliding glass panels offers a real alfresco feeling for those balmy Madeiran days and nights. The exterior terrace with private infinity heated pool is a true balcony over the Atlantic Ocean glamorously charming the bay just under your eyes.
Popular amenities for Estreito da Calheta rentals with a pool
House rentals with a pool

Relax Over The Sea -12391/AL

The Sunset Avenue w/infinity pool(optional heated)

Old Wine Villa

NEW Quinta da Luz - By Your Madeira Rentals

Villa Palheiros - A Magnificent Ocean View

Amazing views, saltwater pool, and BBQ

Typical house above the sea

Casa Sol e Vista
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

Sunny Ocean View Apartment • Pool & Open Horizon

Monumental Apartment

Whitehouse408 Sw.Pool & Pvt. Parking

New dream luxury appartment in the Madeira Palace.
Other vacation rentals with a pool

Quinta Marefe - On the stunning west coast

Tropical Honeymoon Suite

Villa Nicuma by Escape to Madeira

Casa da Lombada

The Paradise - Ocean-Mountains-Jacuzzi-Air Con

Villas Calhau da Lapa 10

Pereira's Domus

Luxury dream villa, outstanding views | Seacrest
Destinations to explore
- Funchal Vacation rentals
- Caniço Vacation rentals
- Arco da Calheta Vacation rentals
- Ribeira Brava Vacation rentals
- Madeira Island Vacation rentals
- Machico Vacation rentals
- La Palma Vacation rentals
- Porto Santo Vacation rentals
- Câmara de Lobos Vacation rentals
- Ponta do Sol Vacation rentals
- San Cristóbal de La Laguna Vacation rentals
- Santa Cruz de La Palma Vacation rentals
- Beachfront rentals Estreito da Calheta
- House rentals Estreito da Calheta
- Rentals with a fire pit Estreito da Calheta
- Rentals with a washer and dryer Estreito da Calheta
- Apartment rentals Estreito da Calheta
- Rentals with a hot tub Estreito da Calheta
- Pet-friendly rentals Estreito da Calheta
- Villa rentals Estreito da Calheta
- Waterfront rentals Estreito da Calheta
- Family-friendly rentals Estreito da Calheta
- Rentals with beach access Estreito da Calheta
- Chalet rentals Estreito da Calheta
- Cottage rentals Estreito da Calheta
- Rentals with a fireplace Estreito da Calheta
- Beach house rentals Estreito da Calheta
- Rentals with outdoor seating Estreito da Calheta
- Rentals with a patio Estreito da Calheta
- Rentals with pools Portugal
- 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
- Pico Do Areeiroo
- PR 11 - Vereda dos Balcões
- Sé do Funchal
- Fish Market
- Ponta do Pargo
- Madeira Whale Museum
- Casas Tipicas de Santana
- Santa Catarina Park
- Cristo Rei
- Blandy's Wine Lodge
- Funchal Cable Car
- CR7 Museum





