
Holiday rentals with a pool in Estreito da Calheta
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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).

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.

Old Town Funchal Seafront villa Pool & garden
Beachfront design home featured in Conde Nast Traveller w private swimming pool & tropical garden in the Old Town of Funchal. Just 200m, 5min walk to the city center, beach & restaurants. Free street parking & fast internet. 2 bedroom villa w 2 bathrooms, living room & kitchen w unlimited sea views. Stylish interiors & lots of outside relaxing, sunbathing & dining space with BBQ. Tropical oasis in the city - feels like the countryside. Perfect base to explore Madeira´s hikes & beaches in style

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)!

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.

Casa Sol e Vista
Villa with a good view and good sunshine throughout the day. The house is located in one of the best places in the parish. It has two bedrooms, living room / kitchen and two bathrooms, with a capacity for 6 people. The house is situated at the top of a hill which makes the house have an extraordinary view. Outside there is a barbecue, a large garden and the swimming pool. Absolute tranquility. Come spend A pleasant vacation in the HOUSE SUN and VIEW. Contact Duarte Paulo

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

Woodlovers Jardim® (Heated Pool Optional) - Unit 1
Settled in a stunning organic green land, contemplating an amazing sea view, spectacular cliffs, surrounded by pieces of cropland, banana plantations and vineyards, we have found what today is WOODLOVERS. Combining this dream place with our engineering, sustainability, renewable energies and permaculture background, we were pioneers in the construction of the first contemporary 100% WoodHouse in Madeira Island respecting the nature and the natural environment.

☀️ Bright & Spacious w/ Pool & Oceanside View :D
Modern studio in the sunny and serene coastal village of Jardim do Mar, south west of Madeira Island. Studio D features an open plan design with kitchenette, lounging area, TV (with Netflix), a cozy queen size bed, a spacious bathroom with washing machine and a private, south facing balcony with ocean and pool view (24° to 26° Celsius). Guests have full access to the garden and heated saltwater pool.

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 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!

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

Casa Velha D. Fernando (Old House D. Fernando)

Casa da Cascata B&B | Levada Houses

Sales House

Casa Cro | Ocean View

Villa Bisa Atlantic View ,heated pool

Kombi Studio(private pool) by STAY Madeira Island

Casa do Lado

Villa Cary
Apartment rentals with a pool

Ocean View Madeira Apartment

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

Ocean view and Infinity pool Apartment

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

Jade Tree Studio at Casa da Vila

Tropical Honeymoon Suite

Cottage Palha, hanging in a tropical garden

Vi Naturae Glamping - Dome 5

Peak A Boo (Private Heated Pool & Private Parking)

Villa Nóbrega

Top View Calheta

Plantation´s Villa - Funchal Seaside Villas
Quick stats about holiday rentals with a pool in Estreito da Calheta

Total holiday rentals
Explore 130 holiday rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 3,940 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
130 of Estreito da Calheta holiday rentals include wifi 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!
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- Cristo Rei
- Madeira Botanical Garden
- Praia do Porto do Seixal
- Casino da Madeira
- Monte Palace Tropical Garden
- Praia da Calheta
- Pico dos Barcelos
- Praia da Madalena do Mar
- Ponta do Sol Beach
- Clube de Golf Santo da Serra
- Complexo Balnear do Lido
- Sé do Funchal
- Zona Velha
- CR7 Museum
- Praia de Garajau
- Santa Catarina Park
- Cascata Dos Anjos
- Ponta de São Lourenço
- Casas Tipicas de Santana
- Praia Machico
- Madeira Whale Museum
- Blandy's Wine Lodge
- Pico Do Areeiroo
- PR 11 - Vereda dos Balcões




