Water Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Zain Gillani

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Water Island 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 $2,045, price is now CA $1,720 per person
CA $1,720
per person
Aug 16 - Aug 21
just found
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
7.2/10 Good! (1,481 reviews)
Everything was ok

Reviewed on Jul 12, 2026

Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Price was CA $3,566, price is now CA $2,867 per person
CA $2,867
per person
Sep 20 - Sep 25
just found
Roundtrip flight included
Toronto (YYZ) to St. Thomas (STT)
9.8/10 Exceptional! (83 reviews)
Our villa was great with incredible views. Any issues or questions we had were quickly resolved. Would highly recommend Calichi to anyone looking to stay on the quiet side of the island.

Reviewed on Jun 15, 2026

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

4.5 out of 5
Price was CA $4,878, price is now CA $3,988 per person
CA $3,988
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to St. Thomas (STT)
9.2/10 Wonderful! (34 reviews)

Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was CA $2,332, price is now CA $1,962 per person
CA $1,962
per person
Sep 20 - Sep 25
just found
Roundtrip flight included
Toronto (YYZ) to St. Thomas (STT)
9.6/10 Exceptional! (31 reviews)
Clean, nice area.

Reviewed on Jul 3, 2026

Villa Marina Vista

Villa Marina Vista

4 out of 5
Price was CA $2,998, price is now CA $2,531 per person
CA $2,531
per person
Aug 16 - Aug 21
just found
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.6/10 Exceptional! (56 reviews)
Love love love! Amazing view, great location, very clean, great pool and the communication was outstanding!!! We will definitely be staying here again.

Reviewed on Jul 8, 2026

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Water Island vacation package cost?
Starting from an incredible CA $1,720, you can tailor make your Water Island vacation package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Water Island?
Creating your own Water Island vacation package with Expedia is one of the easiest ways to save. We have more than 550 airlines and 1,000,000 hotel options all over the world. With such an awesome range to select from, you'll have no difficulty creating your ideal trip.
How far in advance should I book my Water Island vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Most air carriers display prices up to 12 months in advance. Usually, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Water Island are still known to appear just weeks before departure.
What does an Expedia Water Island travel package include?
Expedia has all you need to organize your Water Island getaway, but what goes into your package is entirely up to you. Choose from a combination of flights, rental cars and hotels. Looking for some tours or experiences to keep you entertained? Once you've made your booking, you can add them on too. Whatever your style or budget, there's a package to meet your needs.
What should I know before booking a Water Island travel package?
Locking in all the parts of your escape together is a great way to save. Combine your car rentals, airfares and hotels into a tidy package. But it's not just hotels. Expedia offers all sorts of properties, including vacation rentals like beachfront villas and city residences. You've got loads of choices!
Can I choose my airline with a Water Island Expedia vacation package?
Yes, you can. We offer more than 550 partner airlines across the globe, so opt for the carrier that suits your budget needs.
If I'm not able to travel, can I cancel my Water Island vacation package?
You can cancel your Water Island booking if your plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Stay near popular Water Island attractions

Honeymoon Beach

Why not spend a lazy afternoon at Honeymoon Beach during your trip to Estate Western Water Island?
See properties

What to do in Water Island

Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove

Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove

CA $169
per adult
98% of travellers recommend
Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove
Sunset Sail with Cocktails and Appetizers

Sunset Sail with Cocktails and Appetizers

CA $135
per adult
98% of travellers recommend
Sunset Sail with Cocktails and Appetizers
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

CA $159
per adult
96% of travellers recommend
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT
See all activities in Water Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.