Southside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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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.
Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was CA $2,396, price is now CA $1,948 per person
CA $1,948
per person
Jul 26 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9/10 Wonderful! (29 reviews)
It was absolutely wonderful

Reviewed on Apr 25, 2026

Carina Bay Boutique All Inclusive Resort & Casino

Carina Bay Boutique All Inclusive Resort & Casino

3.5 out of 5
Price was CA $4,270, price is now CA $3,315 per person
CA $3,315
per person
Jul 20 - Jul 30
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Christiansted (STX)
7.6/10 Good! (645 reviews)
Love this place!!! Got the same room as my first trip!!! Awesome!!!

Reviewed on May 11, 2026

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $2,976, price is now CA $2,388 per person
CA $2,388
per person
Jul 26 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
8.2/10 Very Good! (219 reviews)
The resort is very walkable and loved that everything was so close. There is only one dining establishment on the actual resort so would have loved another option but the food at the Long Board was delightful.

Reviewed on Apr 28, 2026

The Frederiksted Hotel

The Frederiksted Hotel

3 out of 5
Downtown Frederiksted
Price was CA $2,867, price is now CA $2,315 per person
CA $2,315
per person
Jul 20 - Jul 30
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Christiansted (STX)
8.4/10 Very Good! (360 reviews)
The AC kept the room cool. We provided our own breakfast.

Reviewed on Apr 27, 2026

Sapphire Sanctuary by the Sea

Sapphire Sanctuary by the Sea

3 out of 5
Price was CA $2,573, price is now CA $2,089 per person
CA $2,089
per person
Jun 15 - Jun 22
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.2/10 Wonderful! (47 reviews)
This place was close to all the amenities and was a comfortable beach side bungalow for grampa to entertain his grandsons and his kids. Cool place. A kitchen to take care of family needs and a step away from beachside bar. The unit itself great for 5 and has 2 nice bathrooms. We had access to snorkeling equipment, beach towels, beach chairs and a great sandy beach.

Reviewed on Nov 23, 2025

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 $477 per night from Jun 10 to Jun 11
CA $477
CA $652 total
Jun 10 - Jun 11
includes taxes & fees
8.4/10 Very Good! (1,218 reviews)
Services are terrible at this hotel. It may be discriminated specfic type of perple. To some, it is extremely friendly with talking and explaining for 20 min. or longer while we were line up to check out for rushing to the airport at the time there were only two customers service representatives ...

Reviewed on May 11, 2026

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 $964 per night from May 21 to May 22
CA $964
CA $1,239 total
May 21 - May 22
includes taxes & fees
9.4/10 Exceptional! (168 reviews)
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Reviewed on May 3, 2026

Buoy Haus Beach Resort St. Thomas, Autograph Collection
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 $339 per night from Jun 2 to Jun 3
CA $339
CA $410 total
Jun 2 - Jun 3
includes taxes & fees
8.8/10 Excellent! (159 reviews)
Imaculate property, central to down town.

Reviewed on May 8, 2026

Hampton by Hilton St. Thomas
See all 3,693 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
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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 $1,948. 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.