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Vacation rentals in Caledon

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Top-rated vacation rentals in Caledon

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Top guest favorite
A small balcony features a round table with a yellow mug and a jar. Two wooden chairs are nearby, and a blanket is draped over one. The scene includes a view of the sea through a wide opening, enhancing the relaxing atmosphere.
Apartment in Hermanus
4.95 out of 5 average rating, 505 reviews

Westcliff Balcony Room

Welcome to this serene and spacious upstairs apartment - with a pool on the one side and a balcony with amazing sea view on the other side. The room itself is warm, cosy and arty. There is plenty of storage, places to sit and relax, access to the pool and safe off street parking. What I love about the room is the feeling you get when you're there... it seems to say 'you're on holiday.. relaaaaxx'. Other 2 apts on the property: /h/westcliff-pool-room-hermanus /h/westcliff-garden-room-hermanus

Top guest favorite
A private boma area features a fire pit surrounded by colorful rock formations and shrubs. Two lounge chairs with striped cushions face a small table set with wine glasses, offering a scenic view of the distant mountains under a softly lit sky.
Guest suite in Sir Lowry's Pass
5 out of 5 average rating, 255 reviews

Intaba Studio Tranquil Getaway w/style & character

An ideal escape, our Studio is a private, self-catering garden unit located on the mountainside on a 300 Ha farm , with a pool (shared), & beaches closeby (15 min). Off the Grid - own power supply & fresh spring water extracted high in the mountains. Panoramic views over sea and mountain landscapes , surrounded by fynbos and wild birdlife , close to Capetown (55 km), airport, (40km) shopping amenities (7km) . Unwind after a busy day and relax at your private boma or around the pool.

Top guest favorite
Double doors with glass panels open to a cozy lounge area visible through the entrance. A wooden deck features a dining table with chairs, surrounded by lush greenery that provides a sense of privacy.
Apartment in Onrus River,
4.99 out of 5 average rating, 189 reviews

Oak & Owl Self-catering Cottage

Come see the whales and taste the wine! Romantic, self-catering cottage with quality finishes in secure estate, Onrus – 25 min walk to beach. Nestled among trees, safe, private, own entrance. Sleeps 2 adults in en-suite bedroom + 2 adults/children on bunk beds in lounge (no children under 2 years plse). Free sherry & firewood! Wi-fi, DSTV, Netflix, free parking. Sun deck with gas BBQ. Quality linen. Aircon. Markets, wine routes & nature walks. Note: There are stairs. GENERATOR FOR LOADSHEDDING

Guest favorite
A heated Jacuzzi with jets is positioned on a private deck, offering expansive views of the sea and surrounding landscape. The wooden structure is complemented by a small side table, with the horizon stretching into the distance under a clear sky.
Guest suite in Vermont
4.84 out of 5 average rating, 290 reviews

Kersbos penthouse situated in Vermont Hermanus

This private unit is situated in Vermont Hermanus, the top floor of a 3 storey house, where you have seaviews on the one side and mountain views on the other. We are 900 m from the well known walkways and about 1.2 km from Davies Pools. 10 km from city centre. There are wine farms, golf courses, fishing, whale watching, hiking trails, art galleries, good restaurants amongs other thing to visit . Wake up to the sound of breaking waves. Sunrise and sunsets are something to enjoy from the stoep. .

Top guest favorite
A wooden deck features a hanging swing chair overlooking expansive views of the landscape and mountains beyond. A wood-fired hottub is visible, with steam rising gently into the air, and modern outdoor furniture is arranged for relaxation.
Cabin in Riviersonderend
5 out of 5 average rating, 103 reviews

Ribbok

Ribbok is situated on a working farm in the Overberg Area. Surrounded by beautiful Renosterbos veld overlooking the Riviersonderend Mountains. Modern self-catering unit that includes the following: Single Bedroom with king size bed Bathroom with shower, toilet, basin Fully equipped kitchen fitted with a gas stove, fridge, microwave, airfryer, toaster, cutlery,crockery Coffee, tea, sugar are provided Free wifi Airconditioning Large deck Wood-fired hottub Braai facilities Fire Wood is provided

Guest favorite
A log cabin is set among green foliage, featuring a spacious wooden deck with a large picnic table and benches. The front porch has comfortable seating and large windows, allowing natural light to flow in. Warm, earthy tones are prominent in the cabin's exterior.
Vacation home in Mereenbosch
4.86 out of 5 average rating, 125 reviews

BushBaby Cabin

BushBaby Cabin is perfect for a romantic get-away. A log cabin beautifully nestled in the milkwood forest, just 20mins from Hermanus - secluded from the busyness of life. Situated by the Botriver lagoon, with a private path for access, this hidden gem brings you to nature's doorstep. Look out for the roaming wild horses and a variety of bird-life. BushBaby is in Meerenbosch with communal pool, tennis courts and table tennis access. Ideal to catch summer sun or a warm, cozy fire in winter.

Guest favorite
A wood-fired hot tub is positioned on a wooden deck, overlooking expansive views of the rolling hills and valleys below. The cloudy sky adds depth to the landscape, while greenery borders the foreground, creating a serene environment.
Home in Overberg District Municipality
4.94 out of 5 average rating, 169 reviews

The Buchu Box

Welcome to The Buchu Box, a contemporary self-catering unit nestled within an essential oils farm, offering breathtaking vistas of the picturesque Overberg in Western Cape. This eco-friendly pod promises a luxurious retreat suitable for couples, solo travelers, and families seeking an escape. Indulge in the epitome of relaxation with our wood-fired hot tub, providing a serene oasis with panoramic views that will leave you spellbound. We have a carbon copy of this unit, The Peppermint Box.

Top guest favorite
A scenic view showcases a tranquil landscape featuring the ocean meeting the shore. Nearby structures include modern homes set against a backdrop of mountains and a clear blue sky. The path leading to the ocean is bordered by lush greenery and rocky elements.
Guesthouse in Pringle Bay
5 out of 5 average rating, 145 reviews

Spectacular ocean views @ 38 on Penguin Studio

Unwind whilst taking in the spectacular 270 degree ocean and mountain views from the comfort of this luxury Pringle Bay studio. Just 100m from the rocky shoreline you will not only be awed by the views but will hear and feel the waves crashing onto the rocks. * Uncapped WiFi (works during load shedding) * King Size Bed * Flat screen TV with Netflix, AppleTV+ and YouTube * Fully equipped kitchen * Fireplace * Heated towel rail * Handheld bidet * Great coffee * Lockable Safe * Hair Dryer

Top guest favorite
A rustic exterior view of a cottage features large wooden sliding doors surrounded by vibrant greenery. A stone path leads to the entrance, with well-maintained flower beds flanking the sides, complemented by a modern roof and solar panels overhead.
Cottage in Cape Winelands District Municipality
4.99 out of 5 average rating, 110 reviews

Heidi's Barn, Franschhoek

Situated on a small holding 5km outside Franschhoek, opposite the exquisite La Motte Wine Estate, Heidi’s Barn offers the perfect self-catering base from which to explore the Winelands. A fire pit, outdoor dining area and a large swimming pool (shared with one other cottage) are perfect for summertime relaxation while an indoor wood-burning fireplace and wooden floors throughout make for a cosy winter escape. The barn runs on mains power with solar back up for load shedding.

Top guest favorite
A small bird with bright yellow-green plumage is perched above its nest, surrounded by vibrant green foliage. Two chicks with open beaks can be seen in the nest, nestled within soft twigs and leaves, awaiting nourishment from their parent.
Guest suite in Stanford
4.96 out of 5 average rating, 369 reviews

Studio suite, kingsize bed, private garden

Escape to a wonderland of rural tranquility. The Bird House is perfect for a weekend getaway, Garden Route stopover or longer stay for touring the Overberg-Hermanus area. Nestled in its own private garden, the stylish suite offers a well-equipped kitchenette, cosy seating & table for eating/work. Relax in the private bird-filled garden, enjoy a braai & experience starlight quiet. Convenient proximity to wedding venues, wine & cheese farms & places for fine food.

Top guest favorite
An outdoor area features a hexagonal hot tub surrounded by grassy space. A picnic table with benches is positioned beneath a large umbrella, while a braai area with a grill stands nearby, offering a scenic view of the surrounding landscape.
Cottage in Caledon
4.95 out of 5 average rating, 136 reviews

Treyntjes River Cottages

Treyntjes Rivier Cottages are about 9 km from Caledon and 25 km from Hermanus. The cottage offer accommodation for up to 4 guests. The cottage consist of 2 bedrooms each with their own en-suite bathroom. The main bedroom with a king size bed, the second bedroom with 2 single beds. The kitchen is fully equipped and the living area offers couches, TV and WIFI Braai facilities are available in the garden. Please note: no day visitors are allowed

Top guest favorite
A spacious lawn extends from a modern garden annex, bordered by neatly trimmed hedges. Large windows reflect the sky, while a wooden bench under a leafy tree offers a serene spot to relax. The backdrop features rolling hills and distant mountains.
Farm stay in Elgin
4.99 out of 5 average rating, 103 reviews

Best Elgin views in serene setting with pool

The Annex at Tree Tops, is a spacious and well-appointed garden annex with incredible views, adjoining the main homestead. This is the perfect couples’ retreat in which to recharge your batteries while overlooking the magnificent Elgin valley. Offering a wood-burning fireplace (free wood provided) for winter and a plunge pool for summer.

Popular amenities for Caledon vacation rentals

When is the best time to visit Caledon?

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Avg. priceR976 ZARR941 ZARR941 ZARR976 ZARR1,028 ZARR959 ZARR802 ZARR819 ZARR784 ZARR941 ZARR924 ZARR941 ZAR
Avg. temp22°C22°C21°C18°C15°C13°C13°C13°C15°C17°C19°C21°C

Frequently Asked Questions

  • How much does it cost to stay in guesthouse rentals in Caledon?

    Experience the best of Caledon with our guesthouse rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Caledon?

    Caledon has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do bed and breakfast rentals in Caledon have free parking?

    Absolutely! We offer over 10 bed and breakfast rentals with free parking in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Caledon have wifi?

    Absolutely! We offer over 10 guesthouse rentals with wifi in Caledon. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Caledon?

    Yes! Work meets play with ease at over 30 vacation rentals in Caledon featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for Bed And Breakfast Rentals in Caledon?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there Caledon vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Caledon, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Caledon?

    Make yourself at home in Caledon by choosing from our most frequently booked neighborhoods. We have over 80 vacation rentals in Caledon, over 70 vacation rentals in Middleton, and over 80 vacation rentals in Bergsig.

Quick stats about vacation rentals in Caledon

  • Total vacation rentals

    Explore 70 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at R174 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 870 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Caledon vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Caledon rentals

  • 4.5 Average rating

    Caledon stays receive an average rating of 4.5 out of 5 from guests