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Family-friendly holiday rentals in Herold's Bay

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Herold's Bay

  • Total holiday rentals

    Explore 70 holiday rentals in Herold's Bay

  • Nightly prices starting at

    Herold's Bay holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 830 verified reviews to help you choose

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 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!

Top-rated family-friendly rentals in Herold's Bay

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious deck is viewed from inside, featuring polished wooden floors and a railing that overlooks the coastline. The ocean stretches out with gentle waves, framed by lush greenery, inviting serene views of the beach and distant horizon.
Home in Groot Brakrivier
4.93 out of 5 average rating, 113 reviews

11 Seekant

This house is built on the sand. Closer to the beach you cannot get. It has excellent views of the coastline. Sit on the deck and watch the dolphins swim by. It's located within a security village with controlled access. There are a lot of amenities in the vicinity, but you don't have to venture out to enjoy your vacation. Your children can play in the sand or ride their bicycles in the street in a safe environment. The house offers an indoor braai and stacking doors to open up the living space.

Top guest favourite
A wooden lodge nestled among lush greenery, showcasing a combination of textured wood and natural foliage. Large windows allow natural light to fill the interior, while vibrant flowers add color to the surroundings, creating a serene and tranquil environment.
Cabin in Wilderness Heights
4.98 out of 5 average rating, 174 reviews

Lodge in the heart of the Wilderness Forest

Rustic charm in the heart of the Wilderness 3km from Wilderness. A cozy forest Lodge which sleeps a total of 6, 2-4 adult guests as well as 2 children or adults in the loft. A third en suite bedroom is accessed via stairs below the Lodge should 4+ adult guests book. This beautiful wooden lodge nestled amongst the treetops is peaceful & private. Cozy living spaces with small open plan kitchen and private deck with views of the ocean and forest. Communal rock pool and bbq area on the property.

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, 133 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 inviting deck overlooks the ocean, featuring a heated pool and comfortable loungers. Glass railings provide unobstructed views of the coastline and surrounding landscape. The serene space offers a tranquil setting for relaxation and enjoyment of natural beauty.
Home in Wilderness
4.97 out of 5 average rating, 232 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 Heights
4.98 out of 5 average rating, 188 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!

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 Heights
4.93 out of 5 average rating, 569 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
The sitting area features large windows that frame panoramic views of the lagoon and ocean. Comfortable seating arrangements of a sofa and armchair surround a wooden coffee table, while a reading nook is positioned to take advantage of the natural light.
Cabin in Wilderness
4.92 out of 5 average rating, 133 reviews

Lagoon View - Wilderness Bushcamp

Lagoon View is a cosy wooden cabin with panoramic views over Wilderness village, the ocean and lagoon. The cabin forms part of the Wilderness Bushcamp and is set on a hilltop 700m above Wilderness village. It's a 5-minute walk downhill into the village or a 2 minute drive in the car.... The cabin sleeps 4 people in 2 rooms. Guests can enjoy the magnificent view from the cosy sitting room or light a braai on the private deck... Please note, there is no WiFi in the unit.

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, 217 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.

Guest favourite
A wooden dining table is surrounded by eight woven chairs, with a central planter holding succulents. The backdrop features a serene sea view, enhanced by soft sunlight filtering through the trees, creating a calm and inviting outdoor dining space.
Flat in Wilderness
4.95 out of 5 average rating, 474 reviews

Stunning Ocean Views. Infinity Blue Apart 2

We are loadshedding free! Infinity Blue is a luxury, secure self catering apartment with spectacular sea views from each room. It is situated in a quiet, private conservancy only a few minutes drive from Wilderness Village and the beach. The three bedrooms are light and beautifully decorated with lots of original artwork. The beds are all Queen or King extra length and there is DSTV and Wifi. There is an abundance of wildlife such as bushbuck and knysna loeries.

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
4.98 out of 5 average rating, 243 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.

Guest favourite
A cozy outdoor seating area is nestled under a wooden pergola, surrounded by vibrant flowers. The cushioned benches face the beach, offering a view of the waves and sand. Lush greenery and a stone pathway add to the inviting landscape.
Cottage in Wilderness
4.87 out of 5 average rating, 207 reviews

On the beach Seaside cottage

Seaside cottage is situated on Wilderness main beach. The cottage has no sea views from the bedrooms but only from the balcony upstairs. Beautiful sea views from the comman area on the grass. Walking distance to the Wilderness village. Ideal getaway for all couples and families. ( not ideal for small children, stairs in cottage and open balcony) No safety gate at stairs. The property is fully walled and has secure parking on the premises for one vehicle.

Top guest favourite
A wooden deck features a glass of white wine on a small table beside a striped cushion. Lush greenery extends toward the coastline, with ocean waves gently breaking against the shore in the distance. The sunset casts a warm glow over the landscape.
Home in Ballots Bay
4.94 out of 5 average rating, 105 reviews

Cliff Top Houses no 24 - Spectacular sea views

Cliff Top Houses no 24 - The Cats Whiskers Discover this secret escape in Ballots nature reserve, surrounded by forest, fynbos and ocean with an inviting splash pool on the deck. Designed by award winning architect, Henry Paine, the house blends exquisitely into the surrounding nature in a combination of light, glass, wood with spectacular views from all areas. Sleeps 6 in 3 ensuite bedrooms with private decks opening onto sea and forest. Solar power

Popular amenities for Herold's Bay family-friendly rentals

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

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Avg. price$222 SGD$145 SGD$161 SGD$161 SGD$156 SGD$159 SGD$159 SGD$146 SGD$204 SGD$181 SGD$150 SGD$266 SGD
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