Family-Friendly Vacation Rentals in South Side, St Thomas: Compare 10+ Sites & Save

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85 Best Family Vacation Rentals in South Side (Starting from $90)

Scotland Villa 2
Scotland Villa 2
Apartment
St Thomas, U.S. Virgin Islands
0.4k from South Side center

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

2 Bedrooms4 Guests
9.6

Exceptional

30 reviews

$153
Average price / night
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Scotland Villa 1
Scotland Villa 1
Apartment
St Thomas, U.S. Virgin Islands
1.7k from South Side center

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

2 Bedrooms4 Guests
9.6

Exceptional

8 reviews

$230
Average price / night
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Wintberg Tropical Villas
Wintberg Tropical Villas
Apartment
Mandal, U.S. Virgin Islands
1.9k from South Side center

Ocean View, Security/Safety, Oceanfront, Pool, View, Wellness Facilities, Barbecue/Outdoor Cooking

8 Bedrooms16 Guests
9.7

Exceptional

38 reviews

$225
Average price / night
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Bed & Shower Stop
Bed & Shower Stop
Apartment
U.S. Virgin Islands
2.1k from South Side center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$90
Average price / night
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Oceanfront Villa with Pool, Hot Tub & 5 Condos! USVI
Oceanfront Villa with Pool, Hot Tub & 5 Condos! USVI
Villa
East End, U.S. Virgin Islands
2.2k from South Side center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom26 Guests
New to Booking
$591
Average price / night
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Layah's Vista
Layah's Vista
Apartment
South Side, U.S. Virgin Islands
2.2k from South Side center

Air Conditioner, Parking, Pool, Internet, Child Friendly

2 Bedrooms4 Guests
7.0

Good

1 reviews

$295
Average price / night
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Point Pleasant Resort
Point Pleasant Resort
Apartment
St Thomas, U.S. Virgin Islands
2.7k from South Side center

Apartments, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms2 Guests
New to Booking
$303
Average price / night
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Beautiful Resort in Margaritaville St. Thomas 1BD
Beautiful Resort in Margaritaville St. Thomas 1BD
House
U.S. Virgin Islands
2.9k from South Side center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom4 Guests
New to Booking
$464
Average price / night
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Penthouse Luxury With Ocean Views Resort Pools
Penthouse Luxury With Ocean Views Resort Pools
House
U.S. Virgin Islands
2.9k from South Side center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom4 Guests
New to Booking
$508
Average price / night
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Bare Feet Retreat
Bare Feet Retreat
House
Frydendal, U.S. Virgin Islands
2.9k from South Side center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

1 Bedroom4 Guests
8.8

Fabulous

21 reviews

$330
Average price / night
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Mahogany Run Retreat A Tranquil Caribbean Escape
Mahogany Run Retreat A Tranquil Caribbean Escape
Apartment
Lovenlund, U.S. Virgin Islands
2.9k from South Side center

Oceanfront, Internet, Security/Safety, Ocean View, Guest Services, Parking, Balcony/Terrace

1 Bedroom3 Guests
9.0

Fabulous

2 reviews

$239
Average price / night
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Saint Thomas Condo with Ocean Views, Walk to Beach!
Saint Thomas Condo with Ocean Views, Walk to Beach!
Apartment
Frydendal, U.S. Virgin Islands
3.0k from South Side center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Beach, Places to stay, Family

1 Bedroom2 Guests
8.6

Fabulous

17 reviews

$190
Average price / night
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Island Daze - Amazing Views
Island Daze - Amazing Views
House
U.S. Virgin Islands
3.1k from South Side center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Hot tubs

1 Bedroom4 Guests
9.0

Fabulous

3 reviews

$376
Average price / night
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Mermaid Escape - Amazing Views!
Mermaid Escape - Amazing Views!
Apartment
U.S. Virgin Islands
3.1k from South Side center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Beach, Places to stay

1 Bedroom2 Guests
10.0

Exceptional

13 reviews

$289
Average price / night
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Mermaid's Hideout Condo - D40 condo
Mermaid's Hideout Condo - D40 condo
Apartment
St Thomas, U.S. Virgin Islands
3.1k from South Side center

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

3 Bedrooms8 Guests
New to Booking
$719
Average price / night
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Aqua Saint Thomas
Aqua Saint Thomas
Apartment
St Thomas, U.S. Virgin Islands
3.1k from South Side center

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

3 Bedrooms10 Guests
7.7

Good

13 reviews

$259
Average price / night
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Hidden Hilltop Treasure
Hidden Hilltop Treasure
Apartment
Charlotte Amalie, U.S. Virgin Islands
3.2k from South Side center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$95
Average price / night
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Wild Ginger Villa
Wild Ginger Villa
Villa
South Side, U.S. Virgin Islands
3.3k from South Side center

Internet, Balcony/Terrace, Pool, Air Conditioner, Parking, Child Friendly

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$704
Average price / night
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St Thomas Cliffside Villa with Pool and Hot Tub!
St Thomas Cliffside Villa with Pool and Hot Tub!
Villa
Lovenlund, U.S. Virgin Islands
3.8k from South Side center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.0

Fabulous

5 reviews

$615
Average price / night
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The Breeze
The Breeze
Apartment
St Thomas, U.S. Virgin Islands
3.9k from South Side center

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

9 Bedrooms30 Guests
5.0

Review score

1 reviews

$400
Average price / night
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The Landmark St Thomas
The Landmark St Thomas
Apartment
Fort Christian, VI, U.S. Virgin Islands
3.9k from South Side center

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

6 Bedrooms16 Guests
7.6

Good

29 reviews

$297
Average price / night
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Midtown Guest House
Midtown Guest House
House
South Side, U.S. Virgin Islands
3.9k from South Side center

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

12 Bedrooms5 Guests
8.3

Very Good

199 reviews

$300
Average price / night
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Little Indigo Apartments
Little Indigo Apartments
Apartment
Mafolie, U.S. Virgin Islands
4.0k from South Side center

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

4 Bedrooms11 Guests
6.8

Good

23 reviews

$222
Average price / night
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Brand New Luxury Private Pool Villa Amber - 5 mins walk to #Sapphire Beach
Brand New Luxury Private Pool Villa Amber - 5 mins walk to #Sapphire Beach
Apartment
U.S. Virgin Islands
4.1k from South Side center

Apartments, Luxury, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom4 Guests
8.5

Very Good

4 reviews

$373
Average price / night
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Brand New Luxury Private Pool Villa Quartz - 5 mins walk to #Sapphire Beach
Brand New Luxury Private Pool Villa Quartz - 5 mins walk to #Sapphire Beach
Apartment
U.S. Virgin Islands
4.1k from South Side center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$373
Average price / night
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The Cottage at Villa Indigo
The Cottage at Villa Indigo
Ski Chalet
Charlotte Amalie, U.S. Virgin Islands
4.2k from South Side center

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

2 Bedrooms5 Guests
7.5

Good

9 reviews

$224
Average price / night
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Villa Indigo Sunny 1BR Apartment in Private Gated Estate
Villa Indigo Sunny 1BR Apartment in Private Gated Estate
Apartment
Charlotte Amalie, U.S. Virgin Islands
4.2k from South Side center

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

1 Bedroom3 Guests
10.0

Exceptional

10 reviews

$222
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 South Side.

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South Side Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 85 verified family-friendly vacation rentals in South Side. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in South Side vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $90 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in South Side 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 South Side 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 South Side often include amenities such as Internet, Child Friendly, and Security/Safety. 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.