Southside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Southside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Carina Bay All Inclusive Resort & Casino - Adults Only
CA $2,661
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Christiansted (STX)
7.4/10 Good! (760 reviews)
The staff were very, very pleasant. The casino was a great place to kill time not a lot to do in the area quite far out from town. The food was OK would’ve liked to see more American food like a fish or a steak but overall it was a great experience,
Reviewed on Sep 11, 2026
Tamarind Reef Resort Spa & Marina
CA $1,564
per person
Dec 4 - Dec 11
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Christiansted (STX)
8.2/10 Very good! (604 reviews)
I was not able to update my rating on the website, but I rate my stay 5 stars. The room overlooking the water was clean and comfortable. The restaurant on the property was perfect. I ate there every day. I will definitely come back.
Reviewed on Sep 12, 2026
At Home in the Tropics
CA $2,438
per person
Nov 29 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Thomas (STT)
9.8/10 Exceptional! (184 reviews)
Excellent place to stay on Saint Thomas. The owners are very responsive, friendly, and accommodating. Clean and spacious rooms a short walk from downtown Charlotte Amalie. This is a small, locally owned "hotel" that has an intimate, relaxed vibe. Easy access and parking.
Reviewed on Aug 3, 2026
Southside Hotel Deals
The Westin St. Thomas Beach Resort & Spa
5 Estate Bakkeroe St. Thomas St. Thomas
CA $364
CA $524 total
Oct 1 - Oct 2
includes taxes & fees
Buoy Haus Beach Resort St. Thomas, Autograph Collection
2 Estate Bakkeroe St. Thomas VI
Fully refundableReserve now, pay when you stay
CA $554
CA $770 total
Oct 13 - Oct 14
includes taxes & fees
9.4/10 Exceptional! (207 reviews)
"My husband and I traveled to ST Thomas over the weekend. We were very excited about this new destination since we invested a little extra to stay in what we thought would be a high end establishment. On day two of vacation during the early morning hours a roach was seen in the room. At 4:30am the ..."
Reviewed on Sep 11, 2026
Bolongo Bay Beach Resort
7150 Bolongo St. Thomas St. Thomas
8.2/10 Very good! (1,003 reviews)
"This was the best vacation we have had!! Highly recommend Bolongo Bay!!! Amazing staff and owners!!!"
Reviewed on Sep 11, 2026
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 vacation package cost?
Get ready to book, because a trip to Southside starts from a tempting CA $1,514. 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 vacation 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 vacation?
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 vacation 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 vacation package?
With a vacation 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 vacation package?
Your situation can change unexpectedly, so yes, you can. You may be able to amend or cancel your Southside vacation 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
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.
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.
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.
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.
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.
Limetree Beach
Why not spend a lazy afternoon at Limetree Beach during your trip to Estate Frenchman Bay?
Pirates Treasure Museum
You can spend an afternoon browsing the exhibits at Pirates Treasure Museum during your travels in Charlotte Amalie.
The Virgin Islands Children's Museum
You can take time to visit The Virgin Islands Children's Museum during your travels to Charlotte Amalie.
What to do in Southside
Night Kayak Tour St. Thomas - Westin Frenchman's Reef
CA $109
per adult
96% of travellers recommend
Champagne Sunset Sail from Margaritaville
CA $152
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
