
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$6,266 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).

Villa Palheiros - A Magnificent Ocean View
Perfect home to enjoy the nature and beauty the island of Madeira has to offer. This villa has a stunning ocean view, situated in a very quiet rural area, where you can enjoy a magnificent climate in a swimming pool with endless views. This villa was built and designed to offer the best comfort to its guests. Perfect housing for families, where you can also find all the necessary amenities in a maximum of 5 minutes by car. The air conditioner is a extra service (contact the owner for more info.)

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.

Country House @ Casas Da Vereda
Relax in class at 250 meters high on the sunny South West coast of Madeira, enjoying sunset and ocean views from the heated pool! The Casas Da Vereda are ideally located in a quiet countryside area with nothing but nature between you and the ocean. At 30 minutes drive from Funchal, 5 minutes drive to rock beaches in seaside villages / sand beaches by the marina of Calheta / “levada” walks. Please note that one can rent any combination of Casa Palheiro (T0), Casa Rural (T1), and (Casa Eco T2)!

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.

Mango House
House with superb sun exposure, peaceful and stunning views over the sea and the mountain. Has 2 bedrooms (one with a double bed and the other with two single beds easily convertible into a double bed), a complete bathroom. On the ground floor open space with kitchen / living and dining room and toilet. Furniture and careful decoration. Outside enjoy the garden and the pleasant dining space with incredible views of the sea. The barbecue, mini-pool and shower complete your well-being.

MG House
Um oásis 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

Villa Bisa Atlantic View ,heated pool
A 2 bedroom villa located in Arco da Calheta. the property has 2 modern style bedrooms, 2 and a half luxurious modern bathrooms,outdoor shower ,new modern kitchen, living room, etc... The property has just been renovated,modern decorated with high quality furniture which is extremely comfortable. The villa also includes cable ,Satellite TV and internet. The property on the outside has BBQ ,pool with a panoramic Seaview ,a nice eating area.

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.

Amazing views, saltwater pool, and BBQ
Elegant and cozy house with incredible views and a pool, perfect for moments of rest and exclusivity. The spacious and bright spaces, comfortable beds and thoughtful details create a relaxing atmosphere for families or groups. It has free private parking, ensuring total convenience. The swimming pool and stunning views make this house the ideal setting for a memorable vacation.

Ohana Ocean View by LovelyStay
Welcome to "Ohana Ocean View," a brand-new modern villa in Calheta. This three-bedroom retreat offers a perfect blend of luxury and comfort, designed for the ultimate relaxation. With a private pool and spacious balconies, you can bask in the breathtaking ocean views. The villa is elegantly decorated with contemporary furnishings and equipped with smart TVs for entertainment.
Popular amenities for Estreito da Calheta rentals with a pool
House rentals with a pool

Villa Serenity by Rentallido

Villa Althea by YMR

Villa Vera Garajau - Madeira Island

Casa da Lombada

The Sunset Avenue w/infinity pool(optional heated)

Villa Nóbrega

Panoramic View: Lux 3 bed w/ heated pool

Villa Panorama - Luxury Villa with Jacuzzi-Calheta
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

Sunny Ocean View Apartment • Pool & Open Horizon

Monumental Apartment

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

Farmhouse by Real Vision

Villa Arco-Iris, a Home in Madeira

Vila Aguarelas with pool by Stay Madeira Island

Ocean Dream • Luxury Apt with Large Terrace & Pool

Top View Calheta, villa with pool and jacuzzi

Villas Calhau da Lapa 10

Ocean View Villa | Infinity Pool, Hot Tub, Sauna

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





