Southside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 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.
Oceans at Divi Carina Bay Adults Only

Oceans at Divi Carina Bay Adults Only

4 out of 5
Price was CA $2,004, price is now CA $1,487 per person
CA $1,487
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Christiansted (STX)
7.8/10 Good! (197 reviews)
Very friendly staff. Too much seaweed. Quiet and comfortable. Bartenders are great! But if you really want to enjoy the beach go somewhere else. Taxi rates are really high. Rent a car. Food is good but very low choices.

Reviewed on Jun. 3, 2025

Carina Bay Boutique All Inclusive Resort & Casino

Carina Bay Boutique All Inclusive Resort & Casino

3.5 out of 5
Price was CA $2,870, price is now CA $1,960 per person
CA $1,960
per person
Oct 3 - Oct 7
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Christiansted (STX)
7.8/10 Good! (499 reviews)
Limited stuff. Off season, restaurants were closed. Able to have breakfast and dinner at least.

Reviewed on Aug. 26, 2025

Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $3,447, price is now CA $2,636 per person
CA $2,636
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
8.2/10 Very Good! (195 reviews)
Room very cute and accommodating. Me and my husband brought our 21 yr old daughter and it was nice that our king size bed was in the loft area so our daughter had the downstairs area with the pull out sofa and balcony to give her space as well. The only negative of the room was the carpet had a couple of stains that should have been treated/cleaned.

Reviewed on Aug. 18, 2025

Pirates Pension at Bluebeard's Castle

Pirates Pension at Bluebeard's Castle

3 out of 5
Price was CA $2,855, price is now CA $2,328 per person
CA $2,328
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
8.4/10 Very Good! (751 reviews)
Awesome property, good location close to down town and restaurants. Property overlooking the ocean bay where cruise ship docks. I would definitely recommend this property, you wont regret it and I will return.

Reviewed on Aug. 30, 2025

Sapphire Sanctuary by the Sea

Sapphire Sanctuary by the Sea

3 out of 5
Price was CA $2,910, price is now CA $2,489 per person
CA $2,489
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
9/10 Wonderful! (44 reviews)
The property was very nice, we had everything we needed. We appreciated that there were restaurants available if we didn’t choose to drive anywhere. The beach was beautiful and it was so convenient that there were lounge chairs available on the beach.

Reviewed on Jul. 14, 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, Po Box 7100, St. Thomas, St. Thomas
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Sep 14 to Sep 15
CA $343
CA $497 total
Sep 14 - Sep 15
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 $423 per night from Sep 30 to Oct 1
CA $423
CA $604 total
Sep 30 - Oct 1
includes taxes & fees
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 459 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
Beach Vacations
Family Vacations
Family Vacations

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 $1,487. 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.