Vacation rentals in Herold's Bay

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.

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.

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!

Rust n Reef

Sophisticated coastal getaway. Rust n Reef was founded by Theunis Visser, an entrepreneur with a deep love for global travel, gastronomy and wine. A creation with a simplistic yet sophisticated feel for easy and stylish breaks on the South African coast line. Rust n Reef epitomizes simplistic sophistication and a like for the finer things in life. With a discerning eye for individuality, Rust n Reef merges the beautiful South African coast line with seasoned industrial styled living.

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.

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.

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.

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.

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.

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

PelserPlesier @Oubaai (Full Inverter)

Pure bliss. That’s the feeling that will strike you at PelserPlesier. Want to get away with the family? Planning a weekend of golf with the boys? Dreaming of unwinding with a good book and your favourite wine? Outeniqua Mountains, Indian Ocean, Oubaai Golf Course — everything you need around you! Stop making excuses. Life is short. We look forward to hosting you at PelserPlesier! PS: Installed inverter system to cover LS!

Hidden Leaf Cabin 2 Secluded Forest Cabin

Tucked away in the forest, this private off-grid cabin offers total seclusion and peace. Soak in the outdoor bathtub under the stars, warm up by the fire pit, and enjoy a cozy, rustic interior with everything you need for a relaxing stay. Ideal for couples, solo travelers, or anyone craving quiet and nature. Here there are no distractions—just trees, stars, and serenity. Relax. Recharge. Reconnect