Southside Vacations & Trips from $1,127

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The Latest Southside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

$1,127
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to St. Thomas (STT)
8/10 Very Good! (2,536 reviews)
Calichi at Picture Point

Calichi at Picture Point

Save 100% on your flight
$2,354
per person
Nov 11 - Nov 16
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to St. Thomas (STT)
9.8/10 Exceptional! (84 reviews)
This was our second time in Calichi. I intend to return soon. There is no other place like it in the world.

Reviewed on Aug 14, 2026

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

$1,307
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Thomas (STT)
8.2/10 Very Good! (233 reviews)
This was a 5 star stay, minus the 20+ minutes sales pitch about attending a timeshare seminar with the semi-aggressive trying to book you. Tbh, if that was not there, this would have been perfection. The room was very clean, modern, and comfortable. Much better than we expected. Loved the bracelet cards btw. The pool bar is convenient and Kerry is very nice and made amazing drinks + got us food daily (the veggie wrap was shockingly good, with coleslaw) and customized stuff for our kid. It was a pleasure and we would come back just for her. The security guard is one of those hidden "help everyone" people. It was incredible how much he was helping the workers. Michele (the owner of the scuba shop) was very accommodating for a late 2 day+ snorkel and fins rental. Amazing deal and we only learned about it from Kerry at the bar. Skip the shenanigans at the front and book your catamaran excursion here. Or, rent some high end equipment and go to Brewers Bay to swim with some turtles for free and see some amazing spots. (Free parking too). The water was so nice and warm! Having the pool is wonderful. The only recommendation is some info about trash/etc as it seems every room had the same question. Wonderful experience overall, and thankful for the little kitchen which saved us a lot of money.

Reviewed on Aug 28, 2026

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

$1,445
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Thomas (STT)
9.2/10 Wonderful! (34 reviews)
The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

$1,502
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Thomas (STT)
8.4/10 Very Good! (1,424 reviews)
The staff,property and services were absolutely an outstanding experience 😁

Reviewed on Aug 29, 2026

Find the Best Southside Vacation Packages

Southside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Cyril E. King Airport (STT)

Southside Hotel Deals

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe St. Thomas St. Thomas
$336 nightly
$378 total
Sep 13 - Sep 14
Total with taxes and fees
8.4/10 Very Good! (1,436 reviews)
"The staff,property and services were absolutely an outstanding experience 😁"

Reviewed on Aug 29, 2026

The Westin St. Thomas Beach Resort & Spa
Bolongo Bay Beach Resort

Bolongo Bay Beach Resort

7150 Bolongo St. Thomas St. Thomas
8.2/10 Very Good! (1,002 reviews)
"All inclusive was definitely worth it. Staff were so helpful. Swim gear to borrow on site was a nice plus!"

Reviewed on Aug 27, 2026

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Bolongo Bay Beach Resort
Buoy Haus Beach Resort St. Thomas, Autograph Collection

Buoy Haus Beach Resort St. Thomas, Autograph Collection

2 Estate Bakkeroe St. Thomas VI
Fully refundableReserve now, pay when you stay
$476 nightly
$535 total
Sep 3 - Sep 4
Total with taxes and fees
9.4/10 Exceptional! (201 reviews)
"Best vacation and best proposal. This place was amazing."

Reviewed on Aug 28, 2026

Buoy Haus Beach Resort St. Thomas, Autograph Collection
See all 488 properties in Southside
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Southside attractions

A coastal town with a cruise ship docked, clear turquoise waters, and green hills in the background.

Skyride to Paradise Point

8.6/10 (489 reviews)
Ride high above Charlotte Amalie in a cable car and enjoy breathtaking views across the harbor and downtown area.
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A sandy beach with footprints, a clear blue sky, and a distant island.
Photo by Keith Tucker

Frenchman's Bay

8.0/10 (1 review)
Commune with nature and explore the great outdoors at Frenchman's Bay during your travels in St. Thomas.
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A group of people running into the sea on a beach with clear blue water and a clear sky.

Caribbean Genealogy Library

8.0/10 (7 reviews)
Caribbean Genealogy Library is just one of the places to see in Estate Raphune, so why not enjoy the other things to explore during your travels? Amble around this romantic area's beautiful beaches, or seek out the sailing opportunities.
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Havensight Mall

8.2/10 (348 reviews)
You can search for that perfect souvenir at Havensight Mall during your trip to Charlotte Amalie. Wander the beautiful beaches and waterfront in this romantic area.
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Buck Island Turtle Cove

10.0/10 (6 reviews)
Explore the lovely green spaces of Buck Island Turtle Cove and enjoy the boating in Buck Island. Wander the beautiful beaches and seaside in this romantic area.
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Limetree Beach

Why not spend a lazy afternoon at Limetree Beach during your trip to Estate Frenchman Bay?
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Pirates Treasure Museum

You can spend an afternoon browsing the exhibits at Pirates Treasure Museum during your travels in Charlotte Amalie.
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The Virgin Islands Children's Museum

You can take time to visit The Virgin Islands Children's Museum during your travels to Charlotte Amalie.
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What to do in Southside

Tree Limin' Extreme Zipline

Tree Limin' Extreme Zipline

$155
per adult
100% of travellers recommend
Tree Limin' Extreme Zipline
Key N Go: Guided UTV/ATV Adventure in St. Thomas, USVI

Key N Go: Guided UTV/ATV Adventure in St. Thomas, USVI (1.5-2 HR)

$160
per adult
86% of travellers recommend
Key N Go: Guided UTV/ATV Adventure in St. Thomas, USVI (1.5-2 HR)
Snorkel guide Catie with ocean friends

Half Day Luxury Catamaran Turtle Snorkel And Beach

$159
per adult
100% of travellers recommend
Half Day Luxury Catamaran Turtle Snorkel And Beach
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