Southside Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Southside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Tamarind Reef Resort Spa & Marina

Tamarind Reef Resort Spa & Marina

3.5 out of 5
Price was CA $2,015, price is now CA $1,462 per person
CA $1,462
per person
Jan 22 - Jan 29
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Christiansted (STX)
8.2/10 Very good! (614 reviews)

Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was CA $7,315, price is now CA $5,282 per person
CA $5,282
per person
Jan 18 - Jan 25
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Thomas (STT)
9.6/10 Exceptional! (41 reviews)
View was amazing . Unit itself was very unique

Reviewed on Sep 13, 2026

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was CA $3,187, price is now CA $2,331 per person
CA $2,331
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8/10 Very good! (2,461 reviews)
I actually enjoyed it. The only thing I did like was a little sewage smell but, ot wasn't every day

Reviewed on Oct 31, 2026

Shibui Cove

Shibui Cove

2 out of 5
Price was CA $3,223, price is now CA $2,431 per person
CA $2,431
per person
Dec 2 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
7.6/10 Good! (7 reviews)
I like this hotel location , design of hotel, view from window, and comfortable inside. Some other near pool women destroyed my car of scratches because do not like when I parked near their car. However, very quant and clean hotel. Only what I did not like : no people for help in hotel , all was online .

Reviewed on Oct 10, 2026

The Frederiksted Hotel

The Frederiksted Hotel

3 out of 5
Downtown Frederiksted
Price was CA $2,651, price is now CA $2,004 per person
CA $2,004
per person
Jan 22 - Jan 29
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Christiansted (STX)
8.4/10 Very good! (383 reviews)
quiet and peaceful

Reviewed on Oct 27, 2026

Southside Hotel Deals

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe St. Thomas St. Thomas
The price is CA $536 per night from Nov 29 to Nov 30
CA $536
CA $723 total
Nov 29 - Nov 30
includes taxes & fees
The Westin St. Thomas Beach Resort & Spa
Buoy Haus Beach Resort St. Thomas, Autograph Collection

Buoy Haus Beach Resort St. Thomas, Autograph Collection

3.5 out of 5
2 Estate Bakkeroe St. Thomas VI
Fully refundableReserve now, pay when you stay
The price is CA $706 per night from Nov 1 to Nov 2
CA $706
CA $947 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (226 reviews)
"S’Mija was the BEST! She was extremely nice and helpful. You should pay her more."

Reviewed on Oct 31, 2026

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

Bolongo Bay Beach Resort

3 out of 5
7150 Bolongo St. Thomas St. Thomas
Get rates
Bolongo Bay Beach Resort
See all 508 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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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 $1,462. 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

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

What to do in Southside

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

CA $168
per adult
96% of travellers recommend
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT
Night Kayak Tour St. Thomas - Westin Frenchman's Reef

Night Kayak Tour St. Thomas - Westin Frenchman's Reef

CA $111
per adult
96% of travellers recommend
Night Kayak Tour St. Thomas - Westin Frenchman's Reef
Sunset Sail with Cocktails and Appetizers

Sunset Sail with Cocktails and Appetizers

CA $134
per adult
98% of travellers recommend
Sunset Sail with Cocktails and Appetizers
See all activities in Southside
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.