
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 140 vacation rentals in Estreito da Calheta

Nightly prices starting at
Estreito da Calheta vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

Verified guest reviews
Over 4,200 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
140 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).
LocationFamilyAccess
4.94 out of 5 average rating, 116 reviews
Grey Rock Villa
The Grey Rock Villa proposes 2 en-suite bedrooms for up to 4 guests, and great facilities such as its private heated infinity swimming pool, designer fireplace and kitchen islet and other luxurious pieces of equipment. It blends harmoniously in the cliffy landscape and with the neighbouring 1 bedroom Beige Rock Villa while offering large views over the Atlantic ocean. The Rock Villas can also be rented together: a peaceful and stylish getaway on the South West coast of the island of Madeira.
LocationValueAccuracy
4.96 out of 5 average rating, 76 reviews
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.
ValueFamilyPool
4.97 out of 5 average rating, 113 reviews
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
LocationValueHeating
4.97 out of 5 average rating, 472 reviews
CASA SOL E VISTA 2
A Casa Sol e Vista 2 está localizada num dos melhores locais da freguesia, a par da casa nr 1. dispoe de 2 quartos de dormir, sala / cozinha e 3 casas de banho, com lotaçao para 6 pessoas. A casa esta situada no cimo de uma colina o que faz que a casa tenha uma vista extraordinaria. No exterior tem um churrasco, um grande jardim e a piscina. Absoluta tranquilidade. Venha passar uns dias agradaveis na Casa Sol e Vista 2. Contactar Duarte Paulo
LocationValueOutdoor spaces
4.98 out of 5 average rating, 105 reviews
Eco Fajã Villas - Deluxe - 60m above sea level
High above the coastline is a private sanctuary where luxury meets nature. With sweeping panoramic sea views, a larger heated infinity pool, and an expansive garden, this villa is designed for those who seek space, tranquility, and exclusivity. Its sleek open-plan interiors, flooded with natural light, blend seamlessly with the outdoors, creating an effortless flow between modern comfort and Madeira’s breathtaking landscape.
LocationSleep qualityGetting around
5.0 out of 5 average rating, 6 reviews
Vistas incríveis piscina de água salgada e BBQ
Casa elegante e acolhedora, com vistas incríveis e piscina, perfeita para momentos de descanso e exclusividade. Os espaços amplos e luminosos, as camas confortáveis e os detalhes pensados ao pormenor criam um ambiente relaxante para famílias ou grupos. Dispõe de estacionamento privado gratuito, garantindo total comodidade. A piscina e as vistas deslumbrantes tornam esta casa o cenário ideal para férias memoráveis.
LocationFamilyView
4.85 out of 5 average rating, 20 reviews
Meu Pé de Cacau - Studio Papaia 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.
FamilyLocationDecor
4.99 out of 5 average rating, 225 reviews
Typical house above the sea
"Casa Nambebe" is a typical Madeiran house. Situated on the south slope of Madeira island, it is a great place to relax and enjoy a beautiful view of the sea. The house is placed in the middle of a land of banana trees where the contact with nature is immediate and the infinite pool will have you feel like you're in the ocean. Every sunset is unique. Número de licença ou registo 38381/AL
FamilyLocationAir conditioning
4.99 out of 5 average rating, 200 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.
LocationFamilyView
4.95 out of 5 average rating, 144 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 a handful of 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.
ValueLocationHeating
4.93 out of 5 average rating, 220 reviews
Villa Pérola | Pool & Panoramic Ocean View
Experience Madeira at Villa Pérola, an elegant villa in Arco da Calheta with a private pool and panoramic Atlantic views. With 3 bedrooms, modern interiors and spacious outdoor areas, it’s the perfect place to relax, enjoy spectacular sunsets and spend an unforgettable holiday by the sea.
FamilyLocationView
4.95 out of 5 average rating, 43 reviewsPopular amenities for Estreito da Calheta rentals with a pool
House rentals with a pool

STONE HOUSE
LocationValueKitchen
4.94 out of 5 average rating, 116 reviews
Moradia Syso
FamilyLocationIndoor spaces
4.95 out of 5 average rating, 132 reviews
Mango House
FamilyLocationCleanliness
4.93 out of 5 average rating, 118 reviews
Casa Cro | Ocean View
LocationFamilyIndoor spaces
4.94 out of 5 average rating, 202 reviews
Casa do Penique ORGANIC
FamilyValueAmenities
4.85 out of 5 average rating, 170 reviews
Endless Blue House
FamilyLocationComfort
4.97 out of 5 average rating, 115 reviews
Villa Bisa Atlantic View ,heated pool
FamilyValueGrill
4.97 out of 5 average rating, 159 reviews
Seafront Home in Old Town Funchal w Pool & Garden
ValueFamilyBeach
4.94 out of 5 average rating, 117 reviewsCondo rentals with a pool

Vargem Mar Beach
FamilyValueShared spaces
4.92 out of 5 average rating, 132 reviews
Tropical Sunset D
LocationFamilyHiking
4.96 out of 5 average rating, 101 reviews
Spectacular Ocean and Cliff views with Pool
FamilyValueCleanliness
4.85 out of 5 average rating, 126 reviews
New dream luxury appartment in the Madeira Palace.
LocationValueComfort
4.99 out of 5 average rating, 146 reviews
Charming Lido Flat I
LocationValueIndoor spaces
4.93 out of 5 average rating, 147 reviews
Sunset Paradise, Funchal: sounds of the sea
FamilyLocationParking
4.94 out of 5 average rating, 102 reviews
Renala II "With Pool" by PAUSA Holiday Rentals
ValueLocationDecor
4.95 out of 5 average rating, 102 reviews
Monumental Apartment
LocationFamilyWifi
4.86 out of 5 average rating, 173 reviewsOther vacation rentals with a pool

Villa Acacia- Spectacular Ocean view & heated pool
ValueLocationDecor
4.99 out of 5 average rating, 87 reviews
Casa Eco @ Casas Da Vereda
FamilyLocationBeach
4.92 out of 5 average rating, 64 reviews
Sunny Ocean View Villa - Calma
LocationFamilyDecor
4.96 out of 5 average rating, 23 reviews
Casa dos Reis
LocationFamilyIndoor spaces
5.0 out of 5 average rating, 29 reviews
King´s View (Heated Pool and Sea View)
LocationFamilyLaundry
4.93 out of 5 average rating, 54 reviews
Villa mit großem Pool und fantastischem Blick
FamilyLocationParking
5.0 out of 5 average rating, 66 reviews
Villa Althea by YMR
FamilyLocationPool
5.0 out of 5 average rating, 29 reviews
Luxury Ocean View Villa | Pool I Calheta I Madeira
FamilyLocationAir conditioning
4.98 out of 5 average rating, 46 reviewsDestinations to explore
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- Praia do Porto do Seixal
- Zona Velha
- Monte Palace Tropical Garden
- Praia da Calheta
- Ponta do Sol Beach
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- Porto Moniz Natural Swimming Pools
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