Southside Holidays & Package Deals 2026

Plan, book, travel with confidence
Better together
Save up to NZ$2,400 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Our pick of the best Southside Hotel Deals

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe St. Thomas St. Thomas

NZ$641

7 Sept - 8 Sept

includes taxes & fees

8.4/10 Very good! (1,383 reviews)

"I stayed at the Westin a couple of years ago twice when it was the Marriott Frenchman’s Reef. The upgrades are amazing, but the best part of my state was a staff. The staff was awesome.!"

Reviewed on 12 Aug 2026

Bolongo Bay Beach Resort

7150 Bolongo St. Thomas St. Thomas

8.2/10 Very good! (1,002 reviews)

"As always the staff is super friendly and helpful. I will definitely be back for a third time!"

Reviewed on 12 Aug 2026

Get rates

Buoy Haus Beach Resort St. Thomas, Autograph Collection

2 Estate Bakkeroe St. Thomas VI

Fully refundableReserve now, pay when you stay

NZ$789

11 Sept - 12 Sept

includes taxes & fees

9.4/10 Exceptional! (195 reviews)

"I loved how welcoming and warm the staff were. Valet and the cleaning personnel were also very nice, helpful, and resourceful. The restaurants were excellent."

Reviewed on 10 Aug 2026

See all 474 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.

Frequently asked questions

How much does a Southside holiday package cost?

Get ready to book, because a trip to Southside starts from a tempting . When you combine your flights, hotels and car rentals into a travel package, you'll pick up great deals.

How do I get a cheap travel package to Southside?

Crafting your own Southside holiday package with Expedia is a smart way to save. We have access to more than 550 airlines and 1 000 000 properties across the globe. With such a wonderful range to pick from, you'll have no trouble putting together your next dream escape.

How far in advance should I book my Southside holiday?

It's tricky picking the ideal time for airfares, but we normally say the earlier, the better. Many international journeys on Expedia become available up to 12 months in advance. If you're booking late, don't worry. Discounted prices occasionally appear within a few weeks of departure dates.

What does an Expedia Southside travel package include?

It comes down to what type of escape you have in the works. Southside holiday deals can include car rentals, flights and hotels. You can mix and match to create the travel package that suits you. You can also add on experiences and activities after you've booked to get even bigger discounts.

What should I know before booking a Southside travel package?

Our prices are already low. However, you'll snap up even more savings if you book your hotels, flights and car rentals together. With an Expedia package, you'll always get transparent pricing and tons of choice.

Can I choose my airline with a Southside Expedia holiday package?

With a holiday package, you're always in charge. Whether you'd like to fly to Southside in coach or business class, simply select from the available airline options. Expedia has access to more than 550 airline partners worldwide.

If I'm not able to travel, can I cancel my Southside holiday package?

Your situation can change unexpectedly, so yes, you can. You may be able to amend or cancel your Southside holiday package at no cost within 24 hours of booking. For bookings older than that, you can still make the necessary changes, but your airline, hotel or car rental company may impose a charge. Want more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

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.

See properties

A sandy beach with footprints, a clear blue sky, and a distant island.

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.

See properties

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.

See properties

Havensight Mall

8.2/10 (348 reviews)

You can find the perfect gifts to bring home at Havensight Mall during your stay in Charlotte Amalie. Wander through the beautiful beaches and waterfront in this romantic area.

See properties

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 through the beautiful beaches and seaside in this romantic area.

See properties