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Vacation rentals in Herold's Bay

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Top-rated vacation rentals in Herold's Bay

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

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Top guest favorite
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 favorite
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, 223 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 favorite
A stunning view from the cabin's interior showcases an expansive deck with two lounging chairs positioned against a backdrop of blue sea and sky. Sunlight floods the space, highlighting the wooden beams of the ceiling and the natural scenery outside.
Tiny home in Wilderness
4.98 out of 5 average rating, 164 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 favorite
An outdoor area features a narrow plunge pool with clear turquoise water, set into a gray floor. White walls reflect natural light, while tall wooden slats add texture. Windows flank both sides, providing glimpses of greenery in the surroundings.
Apartment 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 favorite
A spacious deck features two sun loungers with blue and white striped cushions, overlooking a scenic view of Island Lake and the surrounding greenery. The wooden structure showcases a blend of horizontal and vertical lines, with soft natural light enhancing the tranquil outdoor space.
Guesthouse in Wilderness
4.96 out of 5 average rating, 127 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 favorite
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, 534 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 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
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.

Guest favorite
The living area features a spacious couch facing a large TV mounted on the wall. Natural light filters through the curtains, illuminating the room. Decorative elements include woven wall hangings, vases, and a set of tables with various accessories, creating a cozy atmosphere.
Apartment in Oubaai Golf Estate
4.93 out of 5 average rating, 55 reviews

2-Bedroom Golfside Getaway

2-bedroom, 2-bathroom apartment features 2 king size beds with silky Egyptian cotton linens. Cozy up by the indoor fireplace or step out onto the patio to enjoy a built-in braai, breathtaking views and the soothing sound of running water. With unlimited WiFi and a fully equipped kitchen, including a washing machine and dishwasher, your stay is effortless. Plus, enjoy access to the golf course and the picturesque Oubaai Heritage Trail, offering over 8 km of scenic hiking.

Top guest favorite
An outdoor terrace is shown with a dining table made of natural wood, accompanied by comfortable seating. A charcoal kettle braai stands nearby, and a panoramic view of the ocean and sky, painted in soft twilight hues, is visible beyond the balcony's glass railing.
Apartment in Wilderness
4.96 out of 5 average rating, 457 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 favorite
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 favorite
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 favorite
A deck area is shown with a table and four chairs, shaded by a large umbrella. The ocean and beach can be seen in the distance, with rolling waves visible. Green hills frame the background under a clear blue sky.
Vacation home in Herolds Bay
4.82 out of 5 average rating, 74 reviews

Right Cove 1 - 3 bedroom townhouse on the beach

RIght Cove is situated right on Herold's Bay Beach offering a fully equipped three bedroom Townhouse. The lounge has sliding doors leading onto a deck with ocean views and built in braai. The two upstairs bedrooms have sliding doors and balconies with ocean views. The three bedroom apartment can accommodate a maximum of six people. An amazing safe swimming beach right on the door step and tidal pool. Loads of other activities in the area

Popular amenities for Herold's Bay vacation rentals

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

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,945 GYDG$26,764 GYDG$27,182 GYDG$26,555 GYDG$25,300 GYDG$25,718 GYDG$25,718 GYDG$26,345 GYDG$33,873 GYDG$28,018 GYDG$26,555 GYDG$37,427 GYD
Avg. temp20°C21°C19°C18°C16°C14°C13°C13°C14°C16°C17°C19°C

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 vacation rentals in Herold's Bay

  • Total vacation rentals

    Explore 90 vacation rentals in Herold's Bay

  • Nightly prices starting at

    Herold's Bay vacation rentals start at G$4,182 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    80 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!

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