
Vacation rentals in Caledon
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Top-rated vacation rentals in Caledon
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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

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.

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

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. .

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

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.

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.

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

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.

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.

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

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
Other great vacation rentals in Caledon

Skuilkrans Hideaway Cabin with Hot-tub!

Eden Annex, off-grid, wi-fi, pool, views

Upper Mountain Cottage

Kliprivier Cottage

Serenity cabin on the dam

Rivergate | Stable Cottage

Romantic lakeside cottage

Watermill Studios Ocean & Mountainview Cottage
When is the best time to visit Caledon?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
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Avg. price | R976 ZAR | R941 ZAR | R941 ZAR | R976 ZAR | R1,028 ZAR | R959 ZAR | R802 ZAR | R819 ZAR | R784 ZAR | R941 ZAR | R924 ZAR | R941 ZAR |
Avg. temp | 22°C | 22°C | 21°C | 18°C | 15°C | 13°C | 13°C | 13°C | 15°C | 17°C | 19°C | 21°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
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