Family-Friendly Vacation Rentals in Windermere, Western Cape: Compare 10+ Sites & Save

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  4.  Western Cape

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  6.  Windermere

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2284 Best Family Vacation Rentals in Windermere (Starting from $41)

2 bedroom flat in Pinelands near Old Mutual
2 bedroom flat in Pinelands near Old Mutual
Apartment
Cape Town, South Africa
0.8k from Windermere center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$41
Average price / night
Check Availability
Majorca Apartments by BON Hotels
Majorca Apartments by BON Hotels
Apartment
Corner North Bank Lane and Rialto Road, Cape Town, 7441, South Africa
2.7k from Windermere center

Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Housekeeping, Internet, Kitchen, Laundry

8.6

Fabulous

46 reviews

$115
Average price / night
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Beulah Lodge
Beulah Lodge
House
Cape Town, South Africa
1.0k from Windermere center

B&bs, Cheap, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals

22 Bedrooms15 Guests
9.3

Superb

135 reviews

$57
Average price / night
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Escape to a 3-bedroom holiday house, perfectly designed  for a relaxing getaway!
Escape to a 3-bedroom holiday house, perfectly designed for a relaxing getaway!
House
Cape Town, 7460, South Africa
3.0k from Windermere center

Crib, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Pool, Toys

3 Bedrooms6 Guests
New to Booking
$306
Average price / night
Check Availability
Pine Serene
Pine Serene
Apartment
Cape Town, South Africa
1.2k from Windermere center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom3 Guests
New to Booking
$41
Average price / night
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Spacious, cosy, modern and secure family home
Spacious, cosy, modern and secure family home
House
Rugby, 7405, South Africa
3.4k from Windermere center

Barbecue, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms14 Guests
9.0

Fabulous

2 reviews

$297
Average price / night
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Bradclin House
Bradclin House
Apartment
Cape Town, South Africa
1.2k from Windermere center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

4 Bedrooms8 Guests
9.6

Exceptional

20 reviews

$66
Average price / night
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Beautiful 3 bedroom family home!
Beautiful 3 bedroom family home!
House
Cape Town, 7405, South Africa
3.6k from Windermere center

Barbecue, Crib, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$201
Average price / night
Check Availability
Modern Home
Modern Home
Apartment
Windermere, Western Cape, South Africa
1.2k from Windermere center

Barbecue/Outdoor Cooking, Pet Friendly, View, Sports/Activities, Internet, Child Friendly

2 Bedrooms9 Guests
New to Booking
$62
Average price / night
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Luxury 3-bedroom house in Cape Town
Luxury 3-bedroom house in Cape Town
House
Cape Town, 7441, South Africa
4.0k from Windermere center

Barbecue, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
New to Booking
$141
Average price / night
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La Casetta, Garden Retreat
La Casetta, Garden Retreat
Apartment
Cape Town, South Africa
1.3k from Windermere center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
9.0

Fabulous

5 reviews

$41
Average price / night
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Lagoon Beach Hotel Apartments
Lagoon Beach Hotel Apartments
Apartment
1 Lagoon Gate Drive, Cape Town, 7441, South Africa
4.1k from Windermere center

Babysitting, Bar, Breakfast Available, Business Services, Children Club, Elevator, Fitness Equipment, Free Parking, Frontdesk 24 Hour

1 Bedroom2 Guests
7.4

Good

16 reviews

$136
Average price / night
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Inn-Style
Inn-Style
House
Cape Town, South Africa
1.4k from Windermere center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

5 Bedrooms12 Guests
9.0

Fabulous

193 reviews

$132
Average price / night
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Flamingo Villa @ Beach/Pool/ Luxury/Solar Back Up
Flamingo Villa @ Beach/Pool/ Luxury/Solar Back Up
House
Cape Town, 7441, South Africa
4.2k from Windermere center

Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave

4 Bedrooms8 Guests
New to Booking
$343
Average price / night
Check Availability
The Palm in Pinelands
The Palm in Pinelands
Apartment
Cape Town, South Africa
1.4k from Windermere center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
9.4

Superb

49 reviews

$45
Average price / night
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Serenity on the Cape
Serenity on the Cape
Apartment
Cape Town, South Africa
1.5k from Windermere center

Security/Safety, Internet, Pool, Parking, Child Friendly

1 Bedroom4 Guests
New to Booking
$52
Average price / night
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7 Rooms, 8 bathrooms and parking for 9 cars
7 Rooms, 8 bathrooms and parking for 9 cars
House
Cape Town, 7700, South Africa
5.2k from Windermere center

Arcade, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

7 Bedrooms10 Guests
New to Booking
$658
Average price / night
Check Availability
Inverness Manor
Inverness Manor
House
Windermere, Western Cape, South Africa
1.6k from Windermere center

Balcony/Terrace, Parking, Laundry, Security/Safety, Internet, Guest Services, Sports/Activities

2 Bedrooms5 Guests
8.8

Fabulous

13 reviews

$62
Average price / night
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Cosy Victorian Style Full Apartment
Cosy Victorian Style Full Apartment
Apartment
Cape Town, 7700, South Africa
5.4k from Windermere center

Barbecue, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
2.0

Review score

1 reviews

$92
Average price / night
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Modern charm in Pinelands
Modern charm in Pinelands
Apartment
Cape Town, South Africa
1.6k from Windermere center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom2 Guests
7.1

Good

17 reviews

$85
Average price / night
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Prestigious Villa
Prestigious Villa
Villa
Cape Town, 7441, South Africa
6.0k from Windermere center

Balcony, Barbecue, Elevator, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms14 Guests
10.0

Exceptional

2 reviews

$399
Average price / night
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Cape Town Luxury Villa • Pool + City Skyline Views
Cape Town Luxury Villa • Pool + City Skyline Views
Villa
Cape Town, 7915, South Africa
6.6k from Windermere center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$355
Average price / night
Check Availability
Ocean View Lodge @ Ocean 9
Ocean View Lodge @ Ocean 9
Apartment
Cape Town, 7441, South Africa
7.1k from Windermere center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$242
Average price / night
Check Availability
Wild Olive Guest House
Wild Olive Guest House
House
4 Keurboom Road, Claremont, Cape Town, 7708, South Africa
7.4k from Windermere center

AC, Bar, Barbecue, Breakfast Available, Business Services, Free Parking, Heater, Housekeeping, Internet

9.6

Exceptional

92 reviews

$147
Average price / night
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Sunset beach holiday home/Pauline's entire villa \n is a taste of luxury.
Sunset beach holiday home/Pauline's entire villa \n is a taste of luxury.
House
Cape Town, 7441, South Africa
7.5k from Windermere center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Laundry, Living Area

7 Bedrooms14 Guests
6.8

Good

3 reviews

$560
Average price / night
Check Availability
Indoor Solar Heated Pool, Hot Tub, PlayPark, BBQ Room, Table Mountain Views WiFi
Indoor Solar Heated Pool, Hot Tub, PlayPark, BBQ Room, Table Mountain Views WiFi
House
Cape Town, 7500, South Africa
7.6k from Windermere center

Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Hot Tub

4 Bedrooms14 Guests
New to Booking
$766
Average price / night
Check Availability
5hrs back up power, Aircon, Uncapped & unlimted WIFI,5km from Blouberg beach.
5hrs back up power, Aircon, Uncapped & unlimted WIFI,5km from Blouberg beach.
Cottage
Cape Town, 7439, South Africa
7.7k from Windermere center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, Pool, TV

1 Bedroom2 Guests
New to Booking
$60
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Windermere.

Stay Near Windermere's Top Attractions

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Windermere Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2284 verified family-friendly vacation rentals in Windermere. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Windermere vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $41 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Windermere offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Windermere are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Windermere often include amenities such as Child Friendly, Laundry, and Balcony/Terrace. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.