Southside Vacations & Trips from $693

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The Latest Southside Vacation Packages

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Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

Save 100% on your flight
$693
per person
Oct 9 - Oct 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to St. Thomas (STT)
8/10 Very Good! (2,536 reviews)
You have to walk up various hills to get to your room or wait in long lines to be shuttled via a 3 person max golf cart. The cart service is almost nonexistent during early morning hours which means that on most mornings you are walking down to the main building area or parking lot. Sometimes even when you get to the main building the doors are locked and no staff can be reached. Several times I called for golf cart service to be picked up to only be told that the staffers have not arrived or were not scheduled to arrive until later. The food at the restaurant looks great but has no taste or flavor. So for the cost it’s extremely overpriced. You can’t use the beach because of the massive amounts of seaweed and although they clean it everyday it is a lot left and the smell is horrible. If you book through Expedia you are not allowed to use the conceriege desk to book excursions so standing in line to make inquiries is a waste of time. The workers are nice but they do expect to be tipped even for the golf cart service which is beyond guest control.

Reviewed on Aug 30, 2026

The Frederiksted Hotel

The Frederiksted Hotel

Downtown Frederiksted
$1,013
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Christiansted (STX)
8.4/10 Very Good! (377 reviews)
The staff was very helpful and attentive to my needs, whether it was dealing with a WiFi connection issue or helping with using the washer and dryer. Having Estherlyn's right downstairs made it easy to have a quick and delicious breakfast. Definitely looking forward to staying there again.

Reviewed on Aug 17, 2026

The Waves at Cane Bay

The Waves at Cane Bay

$962
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Christiansted (STX)
9.4/10 Exceptional! (373 reviews)
The room & location was absolutely beautiful… however we notice baby roaches on our second day. The sunset dive bar was never open to get your complementary drink. The location is a a bit far from main attractions. If you walk down the rode there are multiple bars and food 10/10. The food onsite was great too but options are limited. One thing we didn’t understand .. we asked for late check out and was denied stating that they are fully booked but online showed vacancies for the same day . It was confirmed that they had openings once our flight delayed. Definitely a great location if you vacation is about relaxation. So beautiful.

Reviewed on Aug 26, 2026

Calichi at Picture Point

Calichi at Picture Point

Save 100% on your flight
$2,354
per person
Nov 11 - Nov 16
found 21 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

Carina Bay All Inclusive Resort & Casino - Adults Only

Carina Bay All Inclusive Resort & Casino - Adults Only

$1,660
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Christiansted (STX)
7.4/10 Good! (756 reviews)

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 14 - Sep 15
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
$431 nightly
$485 total
Sep 12 - Sep 13
Total with taxes and fees
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

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 6 - Sep 7
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 495 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.