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.
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Price was CA $2,534, price is now CA $1,916 per person
CA $1,916
per person
May 29 - Jun 5
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
7.2/10 Good! (1,433 reviews)
10/10 highly recommend!

Reviewed on Apr 28, 2026

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $5,522, price is now CA $3,829 per person
CA $3,829
per person
May 29 - Jun 5
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.2/10 Very Good! (216 reviews)
Clean beautiful property. Small beach with strong tides making it hard to enjoy and swim in. Pool was nice. Onsite restaurant staff were very nice however food was not good.

Reviewed on Apr 25, 2026

Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was CA $4,021, price is now CA $2,878 per person
CA $2,878
per person
May 29 - Jun 5
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8/10 Very Good! (182 reviews)
The room was great but I didn’t get to select the view. I would have preferred a higher floor for more of a water view. We only stayed for 3 nights. I would suggest staying for longer or picking another place. The restaurant options are limited to a beach bistro and a very nice (expensive) dinner restaurant. The room we were in had a kitchenette but without a car and for only 2 full days, it wasn’t worth it for us to bring in any food. The beach was nice. We didn’t go in the pool.

Reviewed on Apr 5, 2026

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was CA $3,511, price is now CA $2,553 per person
CA $2,553
per person
May 29 - Jun 5
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8/10 Very Good! (2,418 reviews)
I will definitely be back

Reviewed on Apr 28, 2026

Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Price was CA $4,704, price is now CA $3,512 per person
CA $3,512
per person
May 29 - Jun 5
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.8/10 Exceptional! (166 reviews)
Everything was perfect, room, view, staff etc spent 5 nights will be back in July for 6 nights

Reviewed on Apr 23, 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 $715 per night from May 12 to May 13
CA $715
CA $925 total
May 12 - May 13
includes taxes & fees
8.4/10 Very Good! (1,196 reviews)
Clean and nice ocean view at the outdoor pool

Reviewed on Apr 28, 2026

The Westin St. Thomas Beach Resort & Spa
Hampton by Hilton St. Thomas

Hampton by Hilton St. Thomas

3 out of 5
Havensight Mall Parcel 2 Charlotte Amalie St. Thomas
Fully refundableReserve now, pay when you stay
The price is CA $368 per night from May 5 to May 6
CA $368
CA $445 total
May 5 - May 6
includes taxes & fees
8.8/10 Excellent! (152 reviews)
Great service, excellent room, breakfast on point and ample parking

Reviewed on Apr 26, 2026

Hampton by Hilton St. Thomas
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 $960 per night from May 11 to May 12
CA $960
CA $1,234 total
May 11 - May 12
includes taxes & fees
9.2/10 Wonderful! (166 reviews)
We really wanted to love everything about this place, but the service is the worst that I have ever experienced at any hotel! They did a great job with the branding and marketing but unfortunately the experience does not live up to the expectation. The staff seemed like they really didn’t want to ...

Reviewed on Apr 26, 2026

Buoy Haus Beach Resort St. Thomas, Autograph Collection
See all 3,689 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.
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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 $1,916. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.