Family-Friendly Vacation Rentals in Root 44, Stellenbosch: Compare 10+ Sites & Save

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384 Best Family Vacation Rentals in Root 44 (Starting from $50)

De Oude Schuur
De Oude Schuur
Apartment
Root 44, Stellenbosch, Western Cape (province), South Africa
1.5k from Root 44 center

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

7 Bedrooms23 Guests
8.2

Very Good

500 reviews

$50
Average price / night
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Webersburg Wine Estate
Webersburg Wine Estate
House
Annandale Road, Stellenbosch, 7600, South Africa
1.3k from Root 44 center

AC, Bar, Barbecue, Business Services, Free Parking, Heater, Housekeeping, Internet, Laundry

9.4

Superb

195 reviews

$294
Average price / night
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Webersburg
Webersburg
House
Root 44, Stellenbosch, Western Cape (province), South Africa
1.8k from Root 44 center

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

23 Bedrooms51 Guests
8.7

Fabulous

318 reviews

$186
Average price / night
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Val de Vine Guesthouse
Val de Vine Guesthouse
House
Drie Lande Farm, R44, Stellenbosch, 7599, South Africa
1.6k from Root 44 center

AC, Bar, Breakfast Included, Free Parking, Heater, Housekeeping, Internet, Outdoor Space, Pool

8.0

Good

31 reviews

$93
Average price / night
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Eikendal Lodge
Eikendal Lodge
Cabin
Stellenbosch, South Africa
2.1k from Root 44 center

Cheap, Accommodations, Pools, Parking, Lodges, Cabins, 4-star, Lodgings, Places to stay

12 Bedrooms24 Guests
9.5

Superb

231 reviews

$108
Average price / night
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San Gabriel Homestead
San Gabriel Homestead
Cottage
R44, Stellenbosch, 7600, South Africa
3.7k from Root 44 center

AC, Barbecue, Business Services, Fireplace, Free Parking, Housekeeping, Internet, Kitchen, Laundry

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$105
Average price / night
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Winelands Golf Lodges 22
Winelands Golf Lodges 22
Cabin
Stellenbosch, South Africa
2.2k from Root 44 center

Accommodations, Pools, Parking, Lodges, Spa, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$365
Average price / night
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The Country Guesthouse
The Country Guesthouse
House
96 Winery Road, Stellenbosch, 7130, South Africa
3.9k from Root 44 center

AC, Babysitting, Bar, Barbecue, Breakfast Included, Business Services, Crib, Free Parking, Housekeeping

8.8

Fabulous

25 reviews

$123
Average price / night
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Winelands Golf Lodges 24
Winelands Golf Lodges 24
Cabin
Stellenbosch, South Africa
2.2k from Root 44 center

Accommodations, Pools, Parking, Lodges, Spa, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$242
Average price / night
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Spacious 5-bedroom family friendly house with Wi-Fi, AC in superb Stellenbosch
Spacious 5-bedroom family friendly house with Wi-Fi, AC in superb Stellenbosch
House
Stellenbosch, 7600, South Africa
4.5k from Root 44 center

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

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$550
Average price / night
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Winelands Golf Lodges 26
Winelands Golf Lodges 26
Cabin
Stellenbosch, South Africa
2.2k from Root 44 center

Accommodations, Pools, Parking, Lodges, Spa, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$287
Average price / night
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Baruch Guest House on Rhodes Noord
Baruch Guest House on Rhodes Noord
House
35 Rhodes North, Stellenbosch, 7613, South Africa
5.6k from Root 44 center

AC, Bar, Breakfast Available, Business Services, Free Parking, Housekeeping, Internet, Laundry, Living Area

9.4

Superb

19 reviews

$171
Average price / night
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Winelands Golf Lodges 27
Winelands Golf Lodges 27
Cabin
Stellenbosch, South Africa
2.2k from Root 44 center

Accommodations, Pools, Parking, Lodges, Spa, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$242
Average price / night
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Baruch Guesthouse on Lovell
Baruch Guesthouse on Lovell
House
29 Lovell Avenue, Stellenbosch, 7600, South Africa
5.6k from Root 44 center

AC, Breakfast Available, Business Services, Crib, Free Parking, Housekeeping, Internet, Laundry, Outdoor Space

9.8

Exceptional

14 reviews

$153
Average price / night
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Winelands Golf Lodges 28
Winelands Golf Lodges 28
Cabin
Stellenbosch, South Africa
2.2k from Root 44 center

Cheap, Accommodations, Pools, Parking, Lodges, Spa, Cabins, Lodgings, Places to stay

2 Bedrooms2 Guests
10.0

Exceptional

1 reviews

$220
Average price / night
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Perfect Luxury 5 Double Bedroom Villa in Secure Luxury Bel'Aire Winelands Estate
Perfect Luxury 5 Double Bedroom Villa in Secure Luxury Bel'Aire Winelands Estate
Villa
Somerset West, 1798, South Africa
5.8k from Root 44 center

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

5 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$402
Average price / night
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Winelands Golf Lodges 1
Winelands Golf Lodges 1
Apartment
Onder-Papegaaiberg, South Africa
2.3k from Root 44 center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Places to stay, Family, Self-catering

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$348
Average price / night
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Villa Helderberg
Villa Helderberg
House
38 Rupert Ave, Cape Town, 7130, South Africa
6.2k from Root 44 center

Barbecue, Breakfast Available, Business Services, Free Parking, Grocery, Heater, Housekeeping, Internet, Laundry

10.0

Exceptional

1 reviews

$84
Average price / night
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Winelands Golf Lodges 2
Winelands Golf Lodges 2
Cabin
Stellenbosch, South Africa
2.3k from Root 44 center

Accommodations, Pools, Parking, Lodges, Spa, Lodgings, Places to stay, Family

4 Bedrooms8 Guests
New to Booking
$383
Average price / night
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Cultivar Guest Lodge
Cultivar Guest Lodge
House
Bonniemile Road Off M12, Stellenbosch, 7599, South Africa
6.3k from Root 44 center

AC, Bar, Barbecue, Breakfast Included, Business Services, Extra Bed, Free Parking, Housekeeping, Internet

9.0

Fabulous

144 reviews

$88
Average price / night
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Winelands Golf Lodges 3
Winelands Golf Lodges 3
Cabin
Stellenbosch, South Africa
2.3k from Root 44 center

Accommodations, Pools, Parking, Lodges, Spa, Lodgings, Places to stay, Family

4 Bedrooms8 Guests
New to Booking
$403
Average price / night
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Confortable villa with stuning views, nice garden and amazing swimming pool
Confortable villa with stuning views, nice garden and amazing swimming pool
Villa
Somerset west, 7130, South Africa
6.5k from Root 44 center

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

4 Bedrooms10 Guests
8.8

Fabulous

8 reviews

$403
Average price / night
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Enjoy privacy in your own small garden apartment in the heart of Stellenbosch
Enjoy privacy in your own small garden apartment in the heart of Stellenbosch
Apartment
Stellenbosch, 7600, South Africa
6.5k from Root 44 center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
New to Booking
$253
Average price / night
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Cozy garden apartment in the heart of Stellenbosch
Cozy garden apartment in the heart of Stellenbosch
Apartment
Stellenbosch, 7600, South Africa
6.5k from Root 44 center

AC, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$241
Average price / night
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Luxurious apartment for 2 with dreamlike panorama view
Luxurious apartment for 2 with dreamlike panorama view
Apartment
Western Cape, 7130, South Africa
6.7k from Root 44 center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$196
Average price / night
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Spacious apartment in walking distance to wonderful restaurants in Stellenbosch
Spacious apartment in walking distance to wonderful restaurants in Stellenbosch
Apartment
Stellenbosch Central, 7600, South Africa
6.8k from Root 44 center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$327
Average price / night
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Perfect area in the heart of historic Stellenbosch. The place to be!
Perfect area in the heart of historic Stellenbosch. The place to be!
Apartment
Stellenbosch Central, 7600, South Africa
6.8k from Root 44 center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
New to Booking
$253
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 Root 44.

Where to stay in Root 44? Best neighborhoods & areas

Root 44 Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 384 verified family-friendly vacation rentals in Root 44. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Root 44 vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $50 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Root 44 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 Root 44 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 Root 44 often include amenities such as Child Friendly, Balcony/Terrace, and Fireplace/Heating. 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.