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.
Sapphire Sanctuary by the Sea

Sapphire Sanctuary by the Sea

3 out of 5
Price was CA $1,809, price is now CA $1,413 per person
CA $1,413
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.2/10 Wonderful! (47 reviews)
The condo was great! Clean and plenty of space for my family of 5!

Reviewed on Dec 6, 2025

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 $4,338, price is now CA $2,892 per person
CA $2,892
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.2/10 Wonderful! (34 reviews)

At Home in the Tropics

At Home in the Tropics

3 out of 5
Price was CA $2,162, price is now CA $1,603 per person
CA $1,603
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.8/10 Exceptional! (180 reviews)
Easy location located right in the city, everything is well within driving distance and some are even walking distance. The amenities are great and the staff/owners are wonderful. Very hospitable place , with beach chairs and umbrellas available to use for the beach and the pool being 50 feet away with a wonderful view. Couldn’t ask for anything better. Would recommend this place to anyone and will be returning in the future.

Reviewed on Jul 5, 2026

Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
Price was CA $2,425, price is now CA $1,830 per person
CA $1,830
per person
Aug 21 - Aug 28
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
9/10 Wonderful! (546 reviews)
I love everything about bluebeards plus it’s clean

Reviewed on Jul 8, 2026

Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was CA $2,745, price is now CA $2,156 per person
CA $2,156
per person
Aug 21 - Aug 28
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to St. Thomas (STT)
8/10 Very good! (187 reviews)
Clean property, but not much to do there. Lovely beach connected to the property and ability to snorkel or kayak, but the boats in the way took away from the beach feel for me…and the food was not worth the cost at all.

Reviewed on Jun 21, 2026

Water Island 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 $604 per night from Jul 21 to Jul 22
CA $604
CA $801 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very good! (1,313 reviews)
"Excellent stay and great location. Staff were great and attentive."

Reviewed on Jul 7, 2026

The Westin St. Thomas Beach Resort & Spa
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
The price is CA $484 per night from Jul 27 to Jul 28
CA $484
CA $545 total
Jul 27 - Jul 28
includes taxes & fees
8/10 Very good! (2,485 reviews)
"Check in was underwhelming. Very bland, it was here are you keys and good luck"

Reviewed on Jul 8, 2026

Margaritaville Vacation Club - St. Thomas
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
The price is CA $308 per night from Jul 21 to Jul 22
CA $308
CA $415 total
Jul 21 - Jul 22
includes taxes & fees
9/10 Wonderful! (584 reviews)
"I love everything about bluebeards plus it’s clean"

Reviewed on Jul 8, 2026

Bluebeard's Castle Resort
See all 3,692 properties in Water Island
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 Water Island vacation package cost?
Starting from an incredible CA $1,413, 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

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

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

CA $112
per adult
98% of travellers recommend
Night Kayak Tour St. Thomas - Westin Frenchman's Reef
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
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.