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Holiday rentals in Herold's Bay

Find and book unique accommodation on Airbnb

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, 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, 231 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, 186 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
The logo features the letters 'RR' elegantly intertwined above the text 'RUST N REEF', all presented in a minimalist design with a contemporary font. A black background accentuates the clean lines and modern aesthetic of the branding.
Apartment in Herolds Bay
4.89 out of 5 average rating, 9 reviews

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.

Guest favourite
A private patio features wooden flooring and a dining table set for two. An outdoor hot tub is visible, surrounded by greenery. The serene dam reflects the clear blue sky, enhancing the natural beauty of the space.
Cabin in George
4.93 out of 5 average rating, 133 reviews

Buff and Fellow Eco Pod 3 (2 sleeper)

Nestled on a beautiful buffalo breeding farm located 10 km from George Airport. Accommodation is offered in a Eco-Friendly POD nestled on the banks of a farm dam. The bedroom contains a king bed which can be converted to 2 single beds, while the en-suite bathrooms are fitted with a bath and outdoor shower. Each unit has a well-equipped kitchen and an open-plan living area with a fireplace. The units open onto a private patio with a built-in braai area and a wood-fired hot tub

Top guest favourite
A freestanding bathtub is positioned next to a large window, offering sweeping views of the ocean at sunset. A glass of wine rests on the tub's ledge, while the soft glow of twilight illuminates the serene scene.
Home in George
4.98 out of 5 average rating, 216 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
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.
Flat in Wilderness
4.95 out of 5 average rating, 472 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, 241 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 cozy sleeping area features a spacious bed with a simple flower placed on the linens. Large windows open to a stunning view of the mountain range, while a small table and chairs are seen on the deck, ideal for enjoying the surrounding nature.
Tiny home in Wilderness
4.94 out of 5 average rating, 631 reviews

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.

Top guest favourite
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
4.91 out of 5 average rating, 256 reviews

Mountain Magic 2 “Sweet Retreat”

Simple, light , warm, north facing converted 12 m container. Nestled on a 6 hectare headland with unparalleled views of the ocean and stunning Outeniqua mountain range. Close to rivers, lagoons, ocean and indigenous forest. Paragliding paradise with a registered site on the property. Decades of local surf knowledge and experience. Happy to point you in the best direction to score something special! We have an abundance of fantastic spots!

Top 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
4.96 out of 5 average rating, 164 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.

Guest favourite
A spacious dining area is showcased, featuring a long wooden table surrounded by multiple light-colored chairs. Large glass doors provide a view of the sea, allowing natural light to fill the room. The interior walls display a light timber finish, enhancing the coastal atmosphere.
Home in Outeniqua Strand
4.98 out of 5 average rating, 204 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

Popular amenities for Herold's Bay holiday rentals

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

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Avg. price$217 SGD$158 SGD$176 SGD$162 SGD$155 SGD$157 SGD$157 SGD$161 SGD$207 SGD$171 SGD$162 SGD$229 SGD
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Frequently Asked Questions

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

    Herolds Bay has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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 30 vacation rentals in Herolds Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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!

  • Do house rentals in Herolds Bay have a kitchen?

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

  • Do house rentals in Herolds Bay have wifi?

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

  • Do apartment rentals in Herolds Bay have free parking?

    Absolutely! We offer over 30 apartment rentals with free parking 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 free parking, over 30 homes with wifi, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Herold's Bay

  • Total holiday rentals

    Explore 100 holiday rentals in Herold's Bay

  • Nightly prices starting at

    Herold's Bay holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 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

    90 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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