Book Holiday Homes in Herolds Bay

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Featured Holiday Homes in Herolds Bay

Five * 4-bedroom house on SA's best golf course. Best views on the estate.

Five * 4-bedroom house on SA's best golf course. Best views on the estate.

Mossel Bay WC
Located in Mossel Bay, this vacation home is by the sea, within a 5-minute drive of Garden Route Casino and Pinnacle Point Beach and Golf Resort.
Opens in a new windowFive * 4-bedroom house on SA's best golf course. Best views on the estate.
Cape St. Blaize

Cape St. Blaize

1 St Blaize Mossel Bay Western Cape
The price is AU$220 per night from 12 Jan to 13 Jan
AU$220
12 Jan - 13 Jan 2026
includes taxes & fees
Located in Mossel Bay, this vacation home is within a 5-minute drive of Cape Saint Blaize Artisanal Distillery and Dias Museum.
Opens in a new windowCape St. Blaize
Stylish & Cozy House - 5min from the beach!

Stylish & Cozy House - 5min from the beach!

Wilderness
When you a stay at this vacation home in Wilderness, you'll be on a river, just steps from Cape Floral Region Protected Areas and Wilderness National Park.
Opens in a new windowStylish & Cozy House - 5min from the beach!
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A comfortable livingroom, fully equipped kitchen make you feel at home apartment

A comfortable livingroom, fully equipped kitchen make you feel at home apartment

Mossel Bay WC
The price is AU$216 per night from 3 Jan to 4 Jan
AU$216
3 Jan - 4 Jan 2026
includes taxes & fees
With a stay at this vacation home in Mossel Bay, you'll be within a 5-minute drive of Hartenbos Seefront and Langeberg Mall.
Opens in a new windowA comfortable livingroom, fully equipped kitchen make you feel at home apartment
Ballots Bay Treehouse by HostAgents

Ballots Bay Treehouse by HostAgents

5 Beach Rd George Western Cape
When you stay at this vacation home in George, you'll be near the beach and 7 minutes by car from Ster-Kinekor Garden Route.
Opens in a new windowBallots Bay Treehouse by HostAgents
stone’s throw from the beach with spectacular sea views.

stone’s throw from the beach with spectacular sea views.

Groot Brakrivier Western Cape
Located in Great Brak River, this vacation home is on a river, within a 5-minute drive of Diaz Beach and Great Brak River Museum.
Opens in a new windowstone’s throw from the beach with spectacular sea views.
303 Kusweg

303 Kusweg

3 out of 5
303 Kusweg Great Brak River Western Cape
Located in Great Brak River, this vacation home is by the sea, within a 10-minute drive of Seeplaas Gallery and Diaz Beach.
Opens in a new window303 Kusweg
Modern house with a breath-taking 180 degree panoramic view of the Indian Ocean.

Modern house with a breath-taking 180 degree panoramic view of the Indian Ocean.

Pinnacle Point WC
Located in Mossel Bay, this vacation home is by the sea, within a 5-minute drive of Garden Route Casino and Pinnacle Point Beach and Golf Resort.
Opens in a new windowModern house with a breath-taking 180 degree panoramic view of the Indian Ocean.
3-bedroom house in amazing Mossel Bay with WiFi

3-bedroom house in amazing Mossel Bay with WiFi

Mossel Bay WC
The price is AU$359 per night from 25 Jan to 26 Jan
AU$359
25 Jan - 26 Jan 2026
includes taxes & fees
With a stay at this vacation home in Mossel Bay, you'll be on the waterfront, just a 3-minute walk from Diaz Beach and 13 minutes by foot from Hartenbos ...
Opens in a new window3-bedroom house in amazing Mossel Bay with WiFi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Herolds Bay Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Herolds Bay vacation homes are the perfect way for you to wing it.

Holiday houses in Herolds Bay let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Herolds Bay in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Herolds Bay adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Herolds Bay with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Herolds Bay vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Herolds Bay Holiday Homes essential information

Accommodation
64 Holiday Homes
Lowest Price
AU$216
Highest Price
AU$359
Popular accommodation
Five * 4-bedroom house on SA's best golf course. Best views on the estate., Cape St. Blaize, Stylish & Cozy House - 5min from the beach!, A comfortable livingroom, fully equipped kitchen make you feel at home apartment, Ballots Bay Treehouse by HostAgents , stone’s throw from the beach with spectacular sea views. , 303 Kusweg, Modern house with a breath-taking 180 degree panoramic view of the Indian Ocean., 3-bedroom house in amazing Mossel Bay with WiFi

Top trending hotels in Herolds Bay

Oubaai Hotel Golf & Spa

Oubaai Hotel Golf & Spa

4 out of 5
406 Herolds Bay Road Herolds Bay Western Cape
The price is AU$241 per night from 16 Jan to 17 Jan
AU$241
16 Jan - 17 Jan 2026
includes taxes & fees
Located in Herolds Bay, Oubaai Hotel Golf & Spa is near the airport, within a 5-minute walk of Oubaai Golf Estate and Freesia Spa.
Opens in a new windowOubaai Hotel Golf & Spa
Dutton's Cove Guesthouse

Dutton's Cove Guesthouse

3 out of 5
21 Rooidraai Avenue Herolds Bay Western Cape
When you stay at Dutton's Cove Guesthouse in Herolds Bay, you'll be near the beach, within a 5-minute drive of Oubaai Golf Estate and Freesia Spa.
Opens in a new windowDutton's Cove Guesthouse
Makarios on Sea

Makarios on Sea

4 out of 5
4 Gericke's Corner Herolds Bay Western Cape
The price is AU$237 per night from 2 Jan to 3 Jan
AU$237
2 Jan - 3 Jan 2026
includes taxes & fees
Located in Herolds Bay, Makarios on Sea is near the bay, within a 5-minute drive of Diaz Beach and Oubaai Golf Estate.
Opens in a new windowMakarios on Sea
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Oppiesee Selfcatering Apartments

Oppiesee Selfcatering Apartments

4 out of 5
28 Beachroad Herolds Bay Western Cape
The price is AU$317 per night from 19 Jan to 20 Jan
AU$317
19 Jan - 20 Jan 2026
includes taxes & fees
Located in Herolds Bay, Oppiesee Selfcatering Apartments is by the ocean, within a 10-minute drive of Oubaai Golf Estate and Freesia Spa.
Opens in a new windowOppiesee Selfcatering Apartments
Don't see what you're looking for?
See all available properties in Herolds Bay
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.