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Holiday houses in Herold's Bay

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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, 122 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.

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, 218 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, 157 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
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 Kleinkrantz
4.93 out of 5 average rating, 246 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.

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
4.93 out of 5 average rating, 524 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
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, 190 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
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
4.92 out of 5 average rating, 51 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 favourite
The River House is nestled among lush greenery, with warm light glowing from its windows at dusk. The surrounding landscape includes rocky cliffs and a pebbled beach, creating a serene coastal environment.
Cabin in Victoria Bay
4.98 out of 5 average rating, 168 reviews

River House - Luxury Cabin -Private Beach access

🪷The Riverhouse is where luxury meets raw nature. Set in Ballots Bay’s untouched reserve, it offers designer comfort, forest views, river sounds, and private beach access. Hike, fish, relax, and reconnect. This peaceful escape is remote, so come prepared—shops are a drive away. Perfect for couples and families seeking serenity and style. As E.M. Forster said, “What is the good of your stars... if they do not enter into our daily lives?” Let them in—book your stay.🪷

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
4.99 out of 5 average rating, 217 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
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
4.97 out of 5 average rating, 152 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.

Top Guest favourite
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 Outeniqua Strand
4.97 out of 5 average rating, 197 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

Guest favourite
A rustic cabin is nestled among trees, featuring a warm wooden exterior. Large glass doors allow natural light to fill the space, with steps leading to the entrance. Surrounding greenery includes shrubs and trees, contributing to the serene, secluded atmosphere.
Cabin in Wilderness
4.98 out of 5 average rating, 180 reviews

Hidden Leaf Cabin 1

A secluded rustic space, Hidden Leaf Cabin 1 is situated amongst trees and nature in Wilderness on the Garden Route. A comfortable and private set up which enables you to fully relax and detach from the outside world. Enjoy a long soak in the outdoor bathtub and sit around the fire pit come evening. You wont want to leave this beautifully unique and private space in the heart of nature.

Popular amenities for Herold's Bay holiday rentals

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

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$258 NZD$223 NZD$226 NZD$221 NZD$211 NZD$214 NZD$214 NZD$219 NZD$282 NZD$237 NZD$204 NZD$286 NZD
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 holiday rentals in Herold's Bay

  • Total holiday rentals

    Explore 90 holiday rentals in Herold's Bay

  • Nightly prices starting at

    Herold's Bay holiday rentals start at $35 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space and kid-friendly amenities

  • Holiday 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 holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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