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  4. Holiday Homes

Side Harbor Holiday Homes

9.8
Exceptional
(43 Reviews)
1841 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Hot Tub
  • Spa
R2,541/Night For 7 Nights R17,794
10.0
Exceptional
(7 Reviews)
796.53 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • View
R2,743/Night For 7 Nights R19,201
9.6
Exceptional
(200 Reviews)
1 Bathroom
Ocean View Resort
  • Spa
  • Pool
  • Ocean View
R13,938/Night For 7 Nights R97,573
6.0
Good
(1 Review)
1453 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Spa
  • Fireplace/Heating
R2,642/Night For 7 Nights R18,497
10.0
Exceptional
(2 Reviews)
968.75 ft² 19 Guests 6 Bedrooms 3 Bathrooms
Ocean View Apartment
  • Private Beach
  • Oceanfront
  • Ocean View
R2,002/Night For 7 Nights R14,016
New
7 Guests 3 Bedrooms 2 Bathrooms
Apartment
  • Fireplace/Heating
  • Air Conditioner
  • Internet
R2,980/Night For 7 Nights R20,869
10.0
Exceptional
(1 Review)
1765.28 ft² 27 Guests 19 Bedrooms 10 Bathrooms
Ocean View Bed & Breakfast
  • Private Beach
  • Oceanfront
  • Hot Tub
R21,323/Night For 7 Nights R149,254
New
883 ft² 6 Guests 2 Bedrooms 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
R2,221/Night For 7 Nights R15,553
10.0
Exceptional
(1 Review)
484.38 ft² 3 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Pool
  • Ocean View
R1,354/Night For 7 Nights R9,486
New
818 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
R2,165/Night For 7 Nights R15,145
9.9
Exceptional
(67 Reviews)
282.56 ft² 10 Guests 8 Bedrooms 4 Bathrooms
Free Cancellation Bed & Breakfast
  • Oceanfront
  • Pool
  • Ocean View
R1,216/Night For 7 Nights R8,505
New
1184 ft² 5 Guests 2 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Fireplace/Heating
  • Pool
R1,912/Night For 7 Nights R13,378

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 511 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. 

More Rentals You May Like Near Side Harbor

9.8
Exceptional
(5 Reviews)
839.58 ft² 6 Guests 2 Bedrooms 1 Bathroom
Free Cancellation Apartment
  • Balcony/Terrace
  • View
  • Pet Friendly
R1,544/Night For 7 Nights R10,811
New
1 Bathroom
Couples Retreat Hotel
R2,715/Night For 7 Nights R19,004
New
1 Bathroom
Couples Retreat Hotel
R2,257/Night For 7 Nights R15,799
New
1 Bathroom
Couples Retreat Hotel
R1,995/Night For 7 Nights R13,967
New
1 Bathroom
Couples Retreat Hotel
R1,815/Night For 7 Nights R12,708
New
1 Bathroom
Hotel
R1,815/Night For 7 Nights R12,708
New
1 Bathroom
Couples Retreat Hotel
R1,178/Night For 7 Nights R8,243
10.0
Exceptional
(6 Reviews)
1076 ft² 5 Guests 2 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Spa
  • Fireplace/Heating
R1,007/Night For 7 Nights R7,049
10.0
Exceptional
(3 Reviews)
1184 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Fireplace/Heating
  • Pool
R1,469/Night For 7 Nights R10,287
10.0
Exceptional
(2 Reviews)
5 Guests 2 Bedrooms 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
R1,861/Night For 7 Nights R13,035
10.0
Exceptional
(2 Reviews)
1184 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Spa
  • Fireplace/Heating
R1,556/Night For 7 Nights R10,892
10.0
Exceptional
(2 Reviews)
1292 ft² 6 Guests 2 Bedrooms 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Spa
  • Fireplace/Heating
R1,381/Night For 7 Nights R9,666