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Side Harbor Holiday Homes

Apartment
Map-icon
like-icon9.8
Exceptional
(43 Reviews)
3 Bedrooms 3 Baths 6 Guests 1841 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
R2,576/Night 7 Nights - R18,036
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Apartment
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
2 Bedrooms 1 Bath 6 Guests 796.53 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R2,778/Night 7 Nights - R19,444
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Resort
Map-icon
like-icon9.6
Exceptional
(210 Reviews)
1 Bath
  • Spa
    Spa
  • Pool
    Pool
More amenities
R16,372/Night 7 Nights - R114,609
Apartment
Map-icon
like-icon6.0
Good
(1 Review)
3 Bedrooms 2 Baths 6 Guests 1453 ft²
  • Oceanfront
    Oceanfront
  • Spa
    Spa
More amenities
R2,674/Night 7 Nights - R18,715
star-icons-3
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
6 Bedrooms 3 Baths 19 Guests 968.75 ft²
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
More amenities
R2,028/Night 7 Nights - R14,194
Apartment
Map-icon
2 Bedrooms 1 Bath 6 Guests 818 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R2,767/Night 7 Nights - R19,378
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Bed & Breakfast
Map-icon
like-icon10.0
Exceptional
(1 Review)
19 Bedrooms 10 Baths 27 Guests 1765.28 ft²
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
More amenities
R21,593/Night 7 Nights - R151,145
Apartment
Map-icon
2 Bedrooms 1 Bath 6 Guests 883 ft²
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
More amenities
R2,691/Night 7 Nights - R18,831
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Bed & Breakfast
Map-icon
like-icon9.9
Exceptional
(71 Reviews)
8 Bedrooms 4 Baths 10 Guests 282.56 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
R1,243/Night 7 Nights - R8,712
Apartment
Map-icon
2 Bedrooms 2 Baths 5 Guests 1184 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R2,340/Night 7 Nights - R16,380
star-icons-4
House
Map-icon
like-icon9.8
Exceptional
(10 Reviews)
2 Bedrooms 2 Baths 8 Guests 1291.67 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R4,207/Night 7 Nights - R29,447
New
Apartment
Map-icon
2 Bedrooms 1 Bath 3 Guests
  • Pet Friendly
    Pet Friendly
  • Air Conditioner
    Air Conditioner
More amenities
R2,028/Night 7 Nights - R14,194

Why Choose Rent By Owner for your Side Harbor Holiday Homes?

What makes our Holiday Homes special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Side Harbor

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Frequently Asked Questions About Side Harbor Holiday Rentals

1. What are the top Holiday Homes in Side Harbor?

There are a lot of options in Side Harbor. If you plan on staying in the Side Harbor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Holiday Homes in Side Harbor:

2. How many Holiday Homes are available in Side Harbor?

Currently, the total number of properties listed by RBO in 2026 is over 536 in the Side Harbor area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Side Harbor. 

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like-icon9.7
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R1,192/Night 7 Nights - R8,347
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like-icon10.0
Exceptional
(6 Reviews)
2 Bedrooms 2 Baths 5 Guests 1076 ft²
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  • Spa
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R1,020/Night 7 Nights - R7,138
Apartment
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 2 Baths 6 Guests 1184 ft²
  • Oceanfront
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  • Fireplace/Heating
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More amenities
R1,488/Night 7 Nights - R10,418
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
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  • Ocean View
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More amenities
R1,885/Night 7 Nights - R13,200
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 6 Guests 1184 ft²
  • Oceanfront
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  • Spa
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R1,576/Night 7 Nights - R11,030
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 6 Guests 1292 ft²
  • Oceanfront
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  • Spa
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More amenities
R1,398/Night 7 Nights - R9,788