Find the best place to stay — Southside

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 HomeAway travelers, the most popular destinations to visit are:

  • Bolongo Bay: 1,356 vacation rentals
  • Bolongo: 63 vacation rentals
  • Estate Frenchman Bay: 1,340 vacation rentals
  • Pistarckle Theater: 1,565 vacation rentals
  • Estate Charlotte Amalie: 1,350 vacation rentals

And HomeAway 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:

  • Estate Frenchman Bay: 1,340 rentals
  • Estate Charlotte Amalie: 1,350 rentals
  • Estate Bolongo: 1,354 rentals
  • Estate Bovoni: 1,356 rentals
  • Estate Bakkero: 1,237 rentals

For other cities, 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?

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

  • Pistarckle Theater: 1,565 rentals
  • Buck Island Turtle Cove: 1,561 rentals
  • Mangrove Lagoon: 1,561 rentals
  • Caribbean Genealogy Library: 1,563 rentals
  • St. John Spice: 1,565 rentals

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

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.

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.

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.

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.

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.