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Holiday rentals in Herold's Bay

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Top-rated holiday rentals in Herold's Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern villa is nestled among lush greenery, showcasing large glass windows that provide a view of the surrounding landscape. The spacious outdoor area features a pathway leading up to the entrance, creating a welcoming approach to the residence.
Villa in Wilderness
4.96 out of 5 average rating, 127 reviews

Ocean View Villa Wilderness

Ocean View Villa Wilderness is a Luxury Villa occupying a prime location at the top of the exclusive residential Constantia Drive in Wilderness. This modern and architectural house is well-designed with ample glass, allowing for light filled interiors offering the same panoramic ocean views as outdoors. Backed up by solar panels and lithium batteries thus not effected by load shedding. Part of the Constantia Kloof conservancy, relax to the sound of the birds as well as that of the ocean.

Top guest favourite
An outdoor deck offers stylish wooden loungers facing a heated pool with panoramic views of the ocean and lagoon. The surrounding landscape features lush greenery, and a dining area with a long table is visible, all beneath a shaded wooden structure.
Home in Wilderness
4.97 out of 5 average rating, 225 reviews

Villa with sea & lagoon view, gym and heated pool

Overlooking the ocean and the lagoon, nestled in a bird conservancy against a forested hill and 5 minute drive from pristine beaches and the center of Wilderness, this stylish self-catering house offers spacious living and dining spaces, a deck with a heated pool, 3 bedrooms with en-suite bathrooms and private terraces with views on the sea and the forest. Amenities include a home gym, Pilates equipment, Weber braai, smart TV 75”, full DSTV, Play Station 4, fussball table, and uncapped Wi-Fi.

Top guest favourite
The image presents a two-level cabin set among lush greenery, featuring solar panels on its roof. A private deck is visible below, with a hot tub and outdoor seating arranged for relaxation, while the stunning ocean view is seen in the background.
Tiny home in Wilderness
4.98 out of 5 average rating, 165 reviews

Luxury Coastal Cabin, Wilderness

Cocoon Cabins- this one’s all about the sea views & hot tub! (ADULTS ONLY, NO KIDS) Enjoy this intimate glass-fronted 2-sleeper nano-cabin set between forest & sea. A considered cabin w/queen bed, compact yet functional kitchen & open-plan bathroom (no bathroom door). In addition find multiple outdoor areas 2 relax in complete privacy. From the outdoor shower to the secluded fire pit, you’ll find many magical touches. As for the views from bed & hot tub, you might never want to get out!

Guest favourite
A bright and airy room features a minimalist design with white walls and a high ceiling. A decorative pendant light hangs above a simple daybed, complemented by soft textiles. Natural light filters through two tall windows, and a slender tree adds an organic touch to the space.
Flat in Kleinkrantz
4.94 out of 5 average rating, 253 reviews

Sky Light Apt 3

Nested beneath the beach dunes of the beautiful and secluded Wilderness beach, Sky Light offers a peaceful and stylish boutique experience. With a spacious room featuring a kitchenette, king size bed, bathroom and l-shaped couch, this sky-lit haven designed from the ground up for your enjoyment includes a plunge pool, five minute walk over the dune to the beach, close proximity to the Wilderness restaurants and Sedgfield Market, paragliding, canoeing and everything that Wilderness offers.

Guest favourite
A wooden deck offers a commanding view of Island Lake, with gently rolling hills and the expansive Serpentine River in the background. A pair of binoculars and a birdwatching guide rest on the table, inviting exploration of the surrounding natural landscape.
Guest house in Wilderness
4.96 out of 5 average rating, 128 reviews

Silverlake Cabin: tranquil expansive views.

Contemporary wood styled cabin with unlimited views of Island Lake, Serpentine River and Outeniqua mountains, allowing for absorbing moments, sunrise to sunset. A gem for outdoor enthusiasts, nature lovers, birders, photographers and those seeking peace and quiet, to recharge and to restore. Paragliding, beaches, and the village of Wilderness all within easy drive, as are neighbouring Garden Route towns and adventure spots. Solar and gas ensure constant power, ideal for remote working.

Top guest favourite
A freestanding bathtub is positioned in front of large diamond-shaped windows, allowing natural light to illuminate the space. Light-colored curtains frame the windows, and a wooden vanity adorned with potted plants sits nearby, contributing to a serene and inviting atmosphere.
Tiny home in Wilderness
4.93 out of 5 average rating, 535 reviews

Magic Garden Cabin, Wilderness Heights

Surrounded by the magic Outeniqua mountains and fynbos, we welcome you to our little slice of wilderness bliss! Our dream for the land is to create a sustainable home and restore this stunning piece of African earth, to live simply and respect nature. We are in the process of rehabilitating our land. We wish to share this wonderful place, its STUNNING views & gardens with like-minded people & travellers and encourage you to explore the beauty that surrounds us here in the Garden Route.

Top guest favourite
A spacious bedroom features a large glass wall providing unobstructed ocean views. A modern freestanding bathtub is positioned near the floor-to-ceiling windows, overlooking the sea. The space is designed with natural materials, enhancing the serene atmosphere.
Home in George
4.98 out of 5 average rating, 195 reviews

Luxury in nature. Solar Powered. Endless sea views

Experience the ultimate coastal lifestyle in our luxury cliff-top home with stunning ocean views from every room. Our organic modern design features natural wood and designer soft furnishings. Dip in our semi heated pool, or enjoy our yoga & chill deck or cook a meal in our designer kitchen. Complete with solar power system & set in a private nature reserve. Just 25 mins from George Airport, 15 mins from the Garden Route Mall and Wilderness. Come unwind in comfort & style.

Top guest favourite
An expansive wooden deck extends from the modern house, offering panoramic views of the ocean. Comfortable wooden loungers are positioned for relaxation, while large glass doors connect the indoor living space to the deck, enhancing the seamless blend of ocean and home.
Home in Ballots Heights, George
4.99 out of 5 average rating, 224 reviews

Stunning location! Heated Pool, Nature, Clifftop!

Backup power supply. 4.4m x 2.4m heated pool. The house is set in a dramatic location perched 60m above the ocean, with endless ocean views. Set in a 94 hectare private , safe reserve, walks and hikes from the front door, come and experience nature in luxury. Whales/Dolphins/wildlife/ stars! 24 hour security 15 minutes to George Mall, 20km from George Airport. The house has 180 degree views over the Ocean, with fresh clean air and the sound of the ocean below.

Top guest favourite
A spacious bedroom opens to a large balcony through glass doors, revealing panoramic views of lush greenery and the ocean beyond. Soft curtains frame the entrance, allowing natural light to fill the room and blending indoor comfort with the scenic outdoor landscape.
Cottage in Mossel Bay
4.97 out of 5 average rating, 109 reviews

Beachcomber Cottage @ Springerbay

Beachcomber Cottage, is a bright and welcoming, solar powered holiday home, set in the beautiful Springerbaai Coastal Estate, with panoramic views of the sea, bay and mountains. The estate boasts access to a pristine sandy beach within around 600 meters from the cottage and also offers a bird hide for bird and game viewing. Everything about Beachcomber Cottage is stylish, fresh, comfortable , and quality. Perfect for couples and small family groups.

Guest favourite
The exterior of the villa is showcased against a dramatic sky, featuring wooden structures that blend with the landscape. Lush greenery surrounds the building, leading to an unobstructed view of the ocean, where the water reflects the soft colors of the clouds above.
Cabin in Ballots Bay
4.97 out of 5 average rating, 154 reviews

Cliff Top Houses no 8 - Endless sea & forest views

Cliff Top Houses are situated in a protected nature reserve perched high on the cliffs and surrounded by forest, fynbos and ocean. These secret hideaways are for those seeking peace, tranquility and that special magic. “The Bee’s Knees” is our spectacular newest secret escape sleeping 4 adults. Situated directly on the cliff edge, enjoy magnificent ocean views, waves crashing on the rocks below and whales so close you can touch them.

Top guest favourite
An outdoor deck is seen, featuring a wooden surface and six chairs arranged around a rectangular table. The space offers unobstructed views of the expansive beach and ocean, with soft sand visible in the distance beneath a cloudy sky.
Home in Outeniqua Strand
4.97 out of 5 average rating, 197 reviews

The Beach House (Where the Dolphins play)

Protected against load shedding The Beach House is situated at the edge of a 20 km long beach. It is a timber house with a white washed finish on the inside. Uniquely located 30 meters from the sea and 5 meters from the Beach. Ideal for walking and relaxing. We generally have schools of Dolphins swim by twice a day throughout the year. Whales can be seen from time to time during the winter and early Spring See security below

Top guest favourite
An outdoor living area is shown, featuring neatly arranged potted plants and a lush green lawn. The porch is shaded, providing a relaxing space. A light-colored seating arrangement is visible in the background, creating a welcoming environment for outdoor enjoyment.
Home in Heather Park
4.94 out of 5 average rating, 104 reviews

3 on Pine, Luxury Home (WiFi, DSTV & Parking incl)

A warm and homely house situated in a upmarket suburb of Heather-park. Everything you'll need for an unforgettable trip to George! Centrally located with a nearby Super Spar and Virgin Active as well as the prestige Fancourt Golf Estate. Approximately 3km from George CBD, with George Airport only a short drive away. Explore the area with its beautiful beaches, majestic Outeniqua Mountains and much more.

Popular amenities for Herold's Bay holiday rentals

When is the best time to visit Herold's Bay?

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Avg. price$187 SGD$162 SGD$164 SGD$161 SGD$153 SGD$155 SGD$155 SGD$159 SGD$205 SGD$169 SGD$161 SGD$226 SGD
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Frequently Asked Questions

  • Do house rentals in Herolds Bay have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Herolds Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Herolds Bay have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Herolds Bay. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Herolds Bay?

    Experience the best of Herolds Bay with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Herolds Bay?

    Yes! Work meets play with ease at over 40 vacation rentals in Herolds Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Herolds Bay have a kitchen?

    Absolutely! We offer over 30 apartment rentals with a kitchen in Herolds Bay. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Herolds Bay?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with a kitchen, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Herolds Bay?

    Herolds Bay has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there Herolds Bay vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Herolds Bay, available on Airbnb. Make a splash and soak up the sun in style!

Quick stats about holiday rentals in Herold's Bay

  • Total holiday rentals

    Explore 90 holiday rentals in Herold's Bay

  • Nightly prices starting at

    Herold's Bay holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    80 of Herold's Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Herold's Bay rentals

  • 4.8 Average rating

    Herold's Bay stays are highly rated by guests – averaging 4.8 out of 5!

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