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Vacation rentals in Calheta

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Top-rated vacation rentals in Calheta

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Guest favorite
The charming stone property features a welcoming entrance with a terracotta roof and vibrant green doors. A small outdoor seating area with a table and chairs is set amidst lush plants and blooming flowers along the pathway, creating an inviting atmosphere.
Home in Arco da Calheta
4.91 out of 5 average rating, 171 reviews

Recanto das Florenças (2) - Great Views & Sunsets

This beautiful stone property, fully restored in 2019, sits in a peaceful rural location called Florenças, a small parish within Calheta, on the southwest region of the island, and has the most amazing panoramic ocean and mountains views. If you’re a nature lover and wish to get away from the noisy and stressful city life, Recanto das Florenças holiday houses offers you a great opportunity to relax and have a romantic or family holiday break, next to the mountains and the beach at the same time!

Guest favorite
The image captures a wooden-roofed structure situated beside a calm sea, with expansive views of the coastline and towering rocky cliffs under a clear blue sky. The serene waters glisten in the sunlight, providing a striking contrast to the natural landscape.
Place to stay in Jardim do Mar
4.95 out of 5 average rating, 278 reviews

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.

Superhost
The image features a charming stone structure with an orange, sloped roof, reflected in the tranquil waters of a heated pool. Colorful stained glass elements adorn the entrance, complemented by planters and a palm tree nearby, all set against a serene blue sky.
Villa in Estreito da Calheta
4.95 out of 5 average rating, 220 reviews

Casa Palheiro @ Casas Da Vereda [Thatched-Roof House]

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)!

Top guest favorite
An aerial view reveals a tropical house surrounded by lush banana plantations, with the ocean and pebbled beach visible in the distance. Nearby houses are set against the backdrop of rugged cliffs, showcasing a blend of natural beauty and coastal charm.
Home in Madalena do Mar
4.97 out of 5 average rating, 197 reviews

Tropical house :) 2 min to the sea, views, nature

Tropical house :) - renovada recentemente, tudo é novo e fresco - ar condicionado na sala - 2 minutos para a praia (50 metros) e estacionamento fácil - vista mar e sunsets deslumbrantes - varanda e pátio privados para refeições no exterior - cozinha totalmente equipada - (forno, máquina de lavar a loiça, microondas, máquina de lavar a roupa, etc) - Internet rápida, smart TV e coluna bluetooth - excelente localização (acesso fácil a toda a ilha, caminhadas e praias) - Check in autónomo

Guest favorite
A modern kitchen is presented, featuring sleek black countertops and white cabinetry. Stainless steel appliances, including a refrigerator and microwave, are visible. A bowl of fresh fruit is placed on the counter, and large glass doors lead to a balcony with scenic views.
Home in Calheta
4.99 out of 5 average rating, 253 reviews

Top View House

Top View House é uma casa nova (remodelada em novembro de 2017) com dois quartos de dormir, uma sala, uma cozinha, duas casas de banho e duas varandas. Situada num bairro calmo em plena natureza com vistas exuberantes. Próxima da Levada Nova e de percursos pedonais (Rabaçal, 25 fontes, Lagoas da Dona Beja e do Vento), também a 10 minutos (de carro) de uma praia de areia amarela, Museu de arte contemporânea da Madeira – Mudas, supermercado, restaurantes, padarias, urgências, farmácia.

Top guest favorite
An outdoor dining area features a wooden table set with dishes and plants, surrounded by a few chairs. The rustic orange exterior of the adjacent building complements the lush greenery. The sea view can be seen in the background under an overcast sky.
Home in Arco Da Calheta
4.93 out of 5 average rating, 108 reviews

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.

Guest favorite
A yurt is positioned amidst vibrant yellow flowers, set against a backdrop of lush greenery. The coastline and a winding road are visible in the distance, with the ocean meeting a partly cloudy sky, creating a serene and natural landscape.
Yurt in Ponta do Sol
4.97 out of 5 average rating, 425 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

Guest favorite
A dining area is highlighted by a large wooden table, illuminated by simple pendant lights. A panoramic window reveals a stunning sunset view over the ocean, while a stone barbecue and stacked wood are visible in the adjacent kitchen space.
Home in Arco Da Calheta
4.92 out of 5 average rating, 278 reviews

Hikers Refuge

Located in Calheta this refuge is ideal for lovers of hiking, with an excellent view of the ocean, you can go 5 minutes walk to the starting point of the levada where you have two options east and west. You can go in 12 minutes by car the levadas of 25 Fontes one of the most beautiful and lovely levadas sought by the walkers. It is also 10 minutes from the beach of Calheta where you can find all that orecisa for your stay, supermarkets, bars, restaurants, etc ...

Guest favorite
Farm stay in Arco da Calheta
4.93 out of 5 average rating, 118 reviews

C Torre Bella Gardens

Welcome to Torre Bela Gardens – Your Perfect Holiday Escape! 🌴🌺 Nestled on a captivating historic estate, your cottage was once the country retreat of British Counts from the island’s earliest days. Surrounded by an exotic fruit farm, a beautifully restored manor house, tranquil gardens, and a charming chapel, there's so much to discover right here. Prepare to be enchanted by incredible viewpoints and a serene atmosphere that invites relaxation. 🌴🍹

Top guest favorite
An infinity-edge pool is illuminated at night, reflecting the starry sky and ocean beyond. Surrounding tropical plants provide a lush backdrop, while a wooden deck extends around the pool, enhancing the tranquil ambiance and offering comfortable seating areas nearby.
Apartment in Paul do Mar
4.99 out of 5 average rating, 212 reviews

Meu Pé de Cacau - Mango Studio in Paúl do Mar

Meu Pé de Cacau is a tropical fruit garden and island retreat 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.

Top guest favorite
The image shows a spacious infinity pool extending towards the ocean, with lounge chairs positioned on the deck. The serene blue water reflects the sky, creating a seamless visual. A seating area is visible in the background, enhancing the outdoor space.
Apartment in Calheta
4.95 out of 5 average rating, 124 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.

Guest favorite
A wooden table is set with a decorative bowl of fruit, a teapot, and a cup. The scene overlooks the vast Atlantic Ocean, framed by lush greenery and steep sea cliffs on the horizon. Bright blue skies contrast beautifully with the vibrant colors below.
Loft in Jardim do Mar
4.88 out of 5 average rating, 342 reviews

Loft in Paradise by SliceofHeavenMadeira

Loft in Paradise is a piece of paradise hidden away from all the noise and chaos. A luxurious open space apartment with one of the most extraordinary views you will ever see. From your king size bed you float above the ocean amidst the sea cliffs that rise towards the heavens. The Atlantic Ocean shines its splendor beneath you displaying all its grandeur and mystic.

Popular amenities for Calheta vacation rentals

Frequently Asked Questions

  • What are the best places to stay in Calheta?

    Travelers often choose the beachside area for easy access to swimming and dining, or hillside neighborhoods for panoramic ocean views and quieter settings. The marina zone has contemporary apartments and quick access to restaurants or boat tours.

  • What are the best things to do in Calheta with kids?

    Families can enjoy the soft sand beach, explore interactive art spaces, or join a guided levada walk with gentle terrain. The marina area often has boat rides suited to children interested in sea life and local views.

  • What are some of the best things to do in Calheta?

    Explore the golden sand beach, visit an art museum featuring contemporary works, or hike along scenic levadas through green hillsides. Guests also enjoy boat tours, sugar cane history sites, and local dining along the waterfront.

  • How is the weather in Calheta?

    Calheta generally has mild, sunny weather with temperatures often ranging from around 65–75°F (18–24°C), though it can be cooler in the hills. Breezes are common near the sea, while higher areas feel fresher after rainfall.

  • When is the best time to visit Calheta?

    Late spring and early fall are often recommended for milder weather and quieter sights around Calheta. Many guests also enjoy the town during seasonal festivals tied to local harvests and traditional parades.

  • What are the best places to visit in Calheta?

    Calheta Beach is popular for its golden sand and swimming, while the contemporary art museum showcases rotating exhibitions. The sugar cane mill offers insights into local history and traditional production methods.

  • What are some hiking trails in Calheta?

    Calheta has several levada trails, including Levada do Rabaçal, known for lush greenery and waterfalls, and Levada Nova, which winds through rural landscapes. These paths often feature scenic ocean and valley views.

  • What are some family activities we can do in Calheta?

    Families frequently enjoy beach outings, easy levada walks, and dolphin-spotting boat trips starting at the marina. Interactive workshops at art centers and visits to agricultural sites are also popular for those traveling with children.

  • What are some of the best day trip ideas from Calheta?

    From Calheta, explore lush nature walks in the Laurisilva Forest, unwind in local agricultural villages, or discover dramatic viewpoints and waterfalls around the western coast. Some guests also explore sea caves or art spaces near the marina.

  • Are there any pet friendly accommodations available in Calheta?

    Calheta has a range of pet-friendly stays, with many hosts welcoming dogs or cats in private homes and apartments. Parks and coastal areas around the town make it convenient for walks or outdoor time with pets.

  • What are some local tips for visiting Calheta?

    Bring comfortable shoes for levada walks, and pack layers to adjust to changing weather in the hills. Visiting local markets in the morning is frequently suggested for fresh produce and regional treats.

  • What is Calheta known for?

    Calheta is known for its golden sand beach, sugar cane traditions, and as a gateway to scenic levada hikes on Madeira's southwestern coast. Its marina, art spaces, and agricultural heritage are frequently highlighted.

  • What are the best hidden gems to explore in Calheta?

    Discover tucked-away viewpoints in rural hamlets, visit small local chapels with historic art, or explore gardens with unique subtropical plants. Creative workshops and artisan studios around the village often surprise guests with hands-on experiences.

  • What are the best foods to try in Calheta?

    Calheta has fresh fish dishes, grilled limpets, and bolo do caco, a local bread made with sweet potato. Locals often enjoy honey cake paired with Madeira wine, and sugarcane rum highlights the area’s agricultural traditions.

  • What should I bring for a trip to Calheta?

    Pack lightweight clothing, a sun hat, and comfortable shoes for walking in town or on levada trails. A light jacket is useful for cooler evenings, and sunscreen is recommended for days by the sea.

  • What is the nightlife in Calheta like?

    Calheta's nightlife centers around relaxed bars, cafes, and waterfront restaurants with occasional live music. Evenings are often enjoyed with local wine, seaside views, and conversation rather than late-night clubs.

  • What are the most popular events or festivals in Calheta?

    Calheta is known for agricultural festivals celebrating local crops, music events near the marina, and seasonal religious celebrations in the main village and surrounding areas. Harvest festivals and traditional parades are frequently suggested for those interested in local culture.

  • Are there family friendly vacation rentals in Calheta?

    Many vacation rentals in Calheta are family friendly, featuring spacious living spaces, private pools, and kitchens for easy meal preparation. Homes around the beach and hillside areas often include amenities suited for travelers with children.

Quick stats about vacation rentals in Calheta

  • Total vacation rentals

    Explore 400 vacation rentals in Calheta

  • Nightly prices starting at

    Calheta vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 15,620 verified reviews to help you choose

  • Family-friendly vacation rentals

    230 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    150 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    400 of Calheta vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Calheta rentals

  • 4.8 Average rating

    Calheta stays are highly rated by guests—averaging 4.8 out of 5!

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