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.

Where to stay around Southside?

Our 2019 property listings offer a large selection of 1,702 vacation rentals near Southside. From 127 Houses to 734 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Southside for a holiday or a weekend are on HomeAway.

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:

  • Estate Bakkero: 1,633 vacation rentals
  • Bolongo: 64 vacation rentals
  • Estate Bolongo: 1,722 vacation rentals
  • Estate Frenchman Bay: 1,705 vacation rentals
  • Frenchman's Bay: 1,693 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 Bakkero: 1,633 rentals
  • Estate Bolongo: 1,722 rentals
  • Estate Frenchman Bay: 1,705 rentals
  • Estate Charlotte Amalie: 1,726 rentals
  • Estate Bovoni: 1,727 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): 1,921 vacation rentals
  • Road Town (RAD-Road Town Seaplane Base): 222 vacation rentals
  • West End (TOV-West End Seaplane Base): 180 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?

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:

  • Mangrove Lagoon: 1,941 rentals
  • Morningstar Beach: 1,941 rentals
  • Bluebeards Beach: 1,936 rentals
  • Virgin Islands National Park: 1,941 rentals
  • Secret Harbour Beach: 1,941 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.

Explore destinations around Southside

Estate Bakkero
1,633 vacation rentals
Estate Bolongo
1,722 vacation rentals
Estate Frenchman Bay
1,705 vacation rentals
Estate Charlotte Amalie
1,726 vacation rentals
Estate Bovoni
1,727 vacation rentals
Estate Hoffman
1,718 vacation rentals
Estate New Herrnhut
1,711 vacation rentals
211 vacation rentals
Estate Smith Bay
1,907 vacation rentals
Estate Chocolate Hole and Great Cruz Bay
1,773 vacation rentals
Estate Nazareth
1,916 vacation rentals
Estate Enighed
1,829 vacation rentals
Estate Peter Bay
1,635 vacation rentals
Charlotte Amalie
1,651 vacation rentals
Estate Hansen Bay
853 vacation rentals
Estate Carolina
1,555 vacation rentals
Fish Bay
1,648 vacation rentals
Estate Johns Folly
1,074 vacation rentals
Road Town
154 vacation rentals
Estate Calabash Boom
1,312 vacation rentals