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Family-friendly vacation rentals in Herold's Bay

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

  • Total vacation rentals

    Explore 80 vacation rentals in Herold's Bay

  • Nightly prices starting at

    Herold's Bay vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

  • Verified guest reviews

    Over 850 verified reviews to help you choose

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Herold's Bay vacation rentals include wi-fi 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 favorite
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 Great Brak River

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.

4.93 out of 5 average rating, 113 reviews
Top guest favorite
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

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.

4.97 out of 5 average rating, 238 reviews
Top guest favorite
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

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.

4.96 out of 5 average rating, 133 reviews
Top guest favorite
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

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.

4.98 out of 5 average rating, 180 reviews
Guest favorite
A modern living area is depicted, featuring a comfortable sofa and coffee table positioned on a dark rug. The kitchenette is visible in the background, with sleek cabinetry and modern appliances. Natural light enters through large sliding doors, which enhance the welcoming ambiance.
Apartment in Mossel Bay

Tip Top Guesthouse

Welcome! Your Home Away from Home! Located in central Mossel Bay, our spacious new upgraded apartment boasts stunning sea and mountain views, perfect for families of four (2 adults, 2 children). Enjoy a large bedroom ( queen size bed) cozy living area with comfortable double sofa bed, and fully equipped kitchen. Relax by the pool and enjoy in/outdoor braai. Unlimited WiFi, Netflix, and DSTV, all you need for a perfect stay. Just 2.5 km from the beach and shopping, it’s the ideal getaway!

4.9 out of 5 average rating, 263 reviews
Top guest favorite
Home in Oubaai Golf Estate

1248 Oubaai, Picturesque Sea-view, Herolds Bay

Stunning unobstructed, sea-view property. Custom designed and located on the exclusive Oubaai Golf Estate in Herolds Bay, with a signature Ernie Els golf course. This house is an entertainer's dream, with all the cooking amenities you can wish for. Enough space to socialize and enjoy the views & sunsets, designed to accommodate 12 ppl, with 5 private en-suite bedrooms, and a separate guest bathroom, everybody will enjoy the comfort and privacy that comes with this luxury property.

4.97 out of 5 average rating, 101 reviews
Top guest favorite
Home in George

Clifftop Ocean View in Nature | Heated Pool

Wake to ocean, fynbos and wildlife from your private clifftop home, 60 metres above the Indian Ocean. Ocean Spirit sits in the secure 94-hectare Ballots Bay Nature Reserve on South Africa’s Garden Route. With panoramic sea views, a private, generously family sized heated pool , backup power and hiking from the front door. Enjoy exceptional privacy, wildlife, seasonal whale and dolphin sightings, star-filled skies and the sound of the ocean. Sleeps 6. Just 20km from George Airport.

4.98 out of 5 average rating, 262 reviews
Top guest favorite
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

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.

4.98 out of 5 average rating, 232 reviews
Guest favorite
Apartment in Wilderness

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.

4.95 out of 5 average rating, 482 reviews
Top guest favorite
A sunset view is captured through the cabin's door, framing two individuals seated at a wooden table. The mountains outline the horizon, creating a peaceful backdrop, while soft lighting from candles adds a serene ambiance to the outdoor dining experience.
Tiny home in Wilderness Heights

Rise and Shine Mountain Cabin, Wilderness Heights

Surrounded by fynbos bush and the sound of birds, you will have a unique nature experience and wake up to the INCREDIBLE views of the majestic Outeniqua mountain range shining in front of you! We are a simple, off the grid set up so do not expect luxury but rather the simple pleasures and nature in all its glory. Our property is a work in progress. We dream of creating a sustainable space by restoring our land and respecting nature in the process.

4.94 out of 5 average rating, 652 reviews
Guest favorite
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

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.

4.96 out of 5 average rating, 176 reviews
Top guest favorite
An open-plan living area features wooden walls and a spacious dining table. Large glass doors provide a view of the ocean, allowing natural light to fill the space. A kitchen area is visible in the background, and outdoor seating is arranged on the deck.
Home in Groot Brakrivier

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

4.98 out of 5 average rating, 208 reviews

Popular amenities for Herold's Bay family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A Kol Kol jacuzzi is situated on a wooden deck, providing a serene view of the horizon at sunset. Soft pastel hues fill the sky, while a grill stands nearby, contributing to a relaxed outdoor atmosphere.
Home in Garden Route District Municipality

Immerson | Luxury Villa | Hot tub | Sun deck

4.96 out of 5 average rating, 106 reviews
Top guest favorite
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

Luxury Coastal Cabin, Wilderness

4.98 out of 5 average rating, 199 reviews
Top guest favorite
A white freestanding bathtub is situated on a wooden deck, surrounded by greenery and elevated views of the mountains. The setting is sheltered by a textured thatched roof, and natural light filters through, enhancing the serene outdoor space.
Shipping container in Hoekwil

Mountain Magic 2 “Sweet Retreat”

4.92 out of 5 average rating, 267 reviews
Guest favorite
Home in Sedgefield

Myoli’s View Pet Friendly Beach House

4.91 out of 5 average rating, 252 reviews
Guest favorite
A cozy bedroom is highlighted by a double bed dressed in crisp white linens. Large glass doors open to a spectacular sea view, allowing natural light to fill the space. A modern bathtub and potted plant are visible in the background.
Apartment in Mossel Bay

Tranquillo Seaview Self Catering Apartment

4.89 out of 5 average rating, 198 reviews
Guest favorite
Home in Mossel Bay

Nolte Ocean Villa Mossel Bay

4.94 out of 5 average rating, 303 reviews
Superhost
A unique structure with a thatched roof and open design is surrounded by palm trees and lush green grass. A spacious patio leads to the entrance, which is flanked by a wood-fired hot tub. Scenic views of the dam and mountains are visible in the background.
Farm stay in George

Buff and Fellow Eco Coconut 6 (2-4 sleeper)

4.87 out of 5 average rating, 143 reviews
Guest favorite
Tent in Wilderness

AfriCamps at Oakhurst on the Garden Route

4.91 out of 5 average rating, 127 reviews

Family- and pet-friendly home rentals

Guest favorite
A charming chalet is set against a forest backdrop, illuminated by warm lighting. Stone steps lead up to the entrance, bordered by lush greenery. A braai area is visible to the side, with a fire pit, inviting a cozy outdoor gathering.
Cabin in Wilderness Heights

Unique cottage in forested setting

4.88 out of 5 average rating, 152 reviews
Guest favorite
An open-plan living area features large glass doors providing unobstructed views of the bay and mountains. Comfortable seating includes a sofa adorned with patterned cushions and a round coffee table. Light streams through the doors, illuminating the modern decor and inviting atmosphere.
Home in Mossel Bay

Cape St. Blaize

4.93 out of 5 average rating, 104 reviews
Guest favorite
A panoramic view captures Santos Beach and the coastline, with the ocean sparkling under sunlight. Lush greenery surrounds a modern infinity pool and outdoor seating area, while various buildings and palm trees populate the landscape, creating a harmonious blend of nature and urban life.
Guesthouse in Mossel Bay

Beach views

4.88 out of 5 average rating, 352 reviews
Guest favorite
A glamping tent is situated on a wooden platform, surrounded by open grassland. Its canvas exterior is complemented by a deck with seating, providing scenic views of the rolling hills and cloudy sky in the background.
Tent in Groot Brakrivier

Favour farm glamping tent 1

4.81 out of 5 average rating, 129 reviews
Guest favorite
Home in Wilderness

Eve's Eden Cottage

4.82 out of 5 average rating, 223 reviews
Guest favorite
A double-story blue home stands against a clear sky, featuring a fenced swimming pool at the foreground. A barbecue area is visible next to the pool, surrounded by a well-maintained garden. Outdoor seating is arranged near the house, emphasizing a relaxed outdoor atmosphere.
Home in Sedgefield

Sedgefield Holiday Accommodation

4.86 out of 5 average rating, 121 reviews
Guest favorite
The lounge area features warm wooden walls and oak flooring. A large flat-screen TV is positioned on a white entertainment unit, accompanied by green potted plants. A fireplace adds warmth, while textured wall sconces provide ambient lighting.
Chalet in Mossel Bay

Summer Villa | Tranquil Mountain Chalet | Retreat

4.88 out of 5 average rating, 124 reviews
Guest favorite
A cozy bedroom features a spacious queen bed adorned with a floral blanket. Two additional single beds are arranged nearby. Towels are neatly placed on the beds, and soft lighting creates a warm ambiance. Wall art depicting feathers adds a subtle decorative touch.
Guesthouse in George

The Frangipani Self-catering Accommodation George

4.88 out of 5 average rating, 111 reviews

Family-friendly home rentals with a pool

Guest favorite
A spacious bedroom features large windows framing the ocean view. The bed is adorned with a soft, dark throw and neatly placed decorative pillows. A television is positioned on a wooden cabinet, while bedside lamps offer gentle lighting. The room is brightly lit by natural light.
Apartment in Wilderness

Shanalulu Sands (full inverter)

4.83 out of 5 average rating, 259 reviews
Top guest favorite
A clear swimming pool is framed by a brick patio, surrounded by lush greenery and flowering plants. Comfortable seating areas are visible on the deck, offering a serene outdoor space that enhances the natural beauty of the setting.
Apartment in George

Camphersdrift - The Secret Garden Cottage

4.94 out of 5 average rating, 172 reviews
Guest favorite
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.
Apartment in Wilderness

Sky Light Apt 3

4.94 out of 5 average rating, 269 reviews
Guest favorite
Two rocking chairs are positioned by an open window, providing an unobstructed view of the beach and ocean. Bright sunlight illuminates the space, highlighting the soft waves lapping against the shore. The calm blue sea complements the serene atmosphere of the apartment.
Apartment in Mossel Bay

Te Waterkant 40 on Diaz beach Hartenbos Mosselbay

4.91 out of 5 average rating, 163 reviews
Guest favorite
A bright bedroom is equipped with two spacious beds adorned with decorative pillows. Natural light enters through large glass doors, leading to a private outdoor area. The wooden flooring complements the serene ambiance, while colorful garden foliage is visible through the windows.
Condo in George

Deluxe 4 pax apartment with stunning Mountain View

4.93 out of 5 average rating, 115 reviews
Guest favorite
The image captures a serene beach scene at sunset, showcasing soft waves lapping at the shore. Warm hues of orange and yellow reflect on the wet sand, while clouds add texture to the sky. The distant horizon is visible, blending seamlessly with the ocean.
Guesthouse in Wilderness

Menjadi - to be...

4.86 out of 5 average rating, 349 reviews
Top guest favorite
An elegantly designed beach house rests among lush vegetation, with a distinctive architectural style. The structure features sweeping lines and large windows that offer panoramic views of the ocean. The expansive blue sea is visible in the background, enhancing the sense of peaceful seclusion.
Villa in Boggomsbaai

Candlewood Beach House

4.93 out of 5 average rating, 149 reviews
Guest favorite
A spacious, modern villa is showcased with multiple levels and expansive glass balconies. The clean white exterior contrasts with the lush greenery in the foreground. The structure allows for abundant natural light, creating an airy and open ambiance.
Villa in Mossel Bay

Luxury Villa with breaker views on Pinnacle Point

4.82 out of 5 average rating, 171 reviews

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

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 632ﺩ.ﺇ 411ﺩ.ﺇ 459ﺩ.ﺇ 588ﺩ.ﺇ 441ﺩ.ﺇ 481ﺩ.ﺇ 452ﺩ.ﺇ 415ﺩ.ﺇ 580ﺩ.ﺇ 514ﺩ.ﺇ 426ﺩ.ﺇ 757
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Destinations to explore