Discover a selection of 2,000 vacation rentals in Southside, VI that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $150 per night, and villas and condos are popular options for a stay in Southside. Either way, you'll find a rental for everyone's needs.
Destination guide

A Saint Thomas Paradise in Southside

Down on the southern edge of Saint Thomas, where the Caribbean waves roll in and the trade winds whisper into the palms, Southside vacation rentals offer somewhere to stay that's just a whisker from the water. You'll wake to the sound of the sloshing sea and have blinding white beaches on the doorstep. Pads with salt-washed decks are available for those evening sunset cocktails, while others have infinity pools that seem to merge with the sky and the sky-blue waters in front of them. They could just be the paradise you've been searching for.

Things to do

History and heights in Southside

If you can pull yourself away from the secluded coves of Southside for just a day or 2, you can wiggle along the pretty coast roads to happening Havensight. That's one of the busiest cruise terminals in the world and it's got top-drawer attractions to match. Top of the list for many is the dangling SkyRide gondola that goes to Paradise Point – the views of the Caribbean Sea and the US Virgin Islands are to die for. Others might prefer the living history museum that is Hassel Island. It's awash with British colonial relics and centuries-old forts.


Slow living in Southside

The soft lap of the water against the white-hued beaches and the gentle swaying of the palms set the rhythm of life in Saint Thomas's Southside. This is a place to really crank up the R&R. Mark off plenty of hammock time; you can use it to get through all those novels, sip all those coconuts or just daydream. Make sure you pack the sun cream and the snorkels, too – there are countless places to lay the towel, soak up the rays and splash in Caribbean coves.


When the sun is on Southside

The only real rule when it comes to booking Southside vacation rentals is to avoid the stormy summers. They last from around June to October, ushering in rains and the occasional tropical tempest across the Caribbean as a whole. Most people will look for seaside pads close to the beaches over the winter, with months like December and January the most popular of all. That leaves spring, in April and May, for those who prefer to find fewer crowds clogging up the beaches.

Natural features

Southside's tropical draws

Southside marks the point where the great cruise ships and busy streets of Havensight and Charlotte Amalie give way to the more untamed reaches of the USVI. The upshot is that you can book Southside vacation rentals near the Southside Cas Cay-Mangrove Lagoon Marine Reserve, where simply snorkeling could reveal puffer fish and stingrays between the craggy black rocks and sea pools. Across the water, the Virgin Islands National Park – a patchwork of tropical rainforest and picture-perfect beaches, like Trunk Bay – sprawls over the island of Saint John.

How many vacation rentals are available around Southside, VI?

Our 2020 property listings offer a large selection of 1,860 vacation rentals around Southside. From 617 villa rentals to 732 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Southside?

There are many lovely places to stay for a holiday trip or just for a weekend in Southside. From Vrbo travelers, the top most popular destinations to visit are:

  • Estate Bolongo: 1,884 vacation rentals
  • Estate Bakkero: 1,781 vacation rentals
  • Estate Frenchman Bay: 1,866 vacation rentals
  • Estate Charlotte Amalie: 1,888 vacation rentals
  • Frenchman's Bay: 1,843 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Southside! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Southside?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Southside:

  • Tortola: 192 rentals
  • Road Town: 147 rentals
  • Buck Island: 1,850 rentals
  • Little Jost Van Dyke: 136 rentals
  • Estate Hassel Island: 1,330 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Southside?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Southside are:

  • Cyril E King Airport (STT): 2,105 vacation rentals
  • West End (TOV-West End Seaplane Base): 166 vacation rentals
  • Road Town (RAD-Road Town Seaplane Base): 205 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Southside?

Vrbo offers a large selection of rentals near lovely places in Southside. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Havensight Mall: 2,089 rentals
  • Mangrove Lagoon: 2,111 rentals
  • Skyride to Paradise Point: 2,087 rentals
  • Bluebeards Beach: 2,088 rentals
  • Mango Tango Art Gallery: 2,087 rentals

But there are many other points of interest around Southside listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Southside

Havensight Mall
2,089 vacation rentals
Mangrove Lagoon
2,111 vacation rentals
Skyride to Paradise Point
2,087 vacation rentals
Bluebeards Beach
2,088 vacation rentals
Mango Tango Art Gallery
2,087 vacation rentals
Morningstar Beach
2,087 vacation rentals
Caribbean Genealogy Library
2,087 vacation rentals
Buck Island Turtle Cove
2,102 vacation rentals
The Butterfly Garden
2,085 vacation rentals
Virgin Islands National Park
2,087 vacation rentals
Honeymoon Beach
2,066 vacation rentals
Sunset Beach
2,063 vacation rentals
Magens Bay
2,089 vacation rentals
Mahogany Run Golf Course
2,085 vacation rentals
Secret Harbour Beach
2,108 vacation rentals
Cinnamon Bay
2,092 vacation rentals
Virgin Islands Folk Museum
201 vacation rentals
Catherineberg Ruins
2,064 vacation rentals
Cane Garden Bay Beach
201 vacation rentals
Coki Beach
2,120 vacation rentals