Pelican Key Vacation Packages

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Top Holiday Package Deals in Pelican Key

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $1,540, price is now CA $1,109 per person
CA $1,109
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,000 reviews)
Nice

Reviewed on Jul 6, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,335, price is now CA $1,504 per person
CA $1,504
per person
Sep 6 - Sep 13
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,442 reviews)
Stayed for 4 days and had the breakfast included in our stay. It is in a location where you can walk to local shops and restaurants. Great experience.

Reviewed on Jul 5, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,482, price is now CA $1,723 per person
CA $1,723
per person
Aug 15 - Aug 22
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,837 reviews)
A

Reviewed on Jul 6, 2026

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was CA $2,533, price is now CA $1,840 per person
CA $1,840
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,007 reviews)
Amazing

Reviewed on Jun 27, 2026

Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was CA $2,209, price is now CA $1,635 per person
CA $1,635
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (629 reviews)
I really liked room design

Reviewed on Jul 4, 2026

Pelican Key Hotel Deals

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $300 per night from Aug 3 to Aug 4
CA $300
CA $369 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,859 reviews)
"A"

Reviewed on Jul 6, 2026

Simpson Bay Resort, Marina & Spa
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
The price is CA $175 per night from Jul 19 to Jul 20
CA $175
CA $221 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,632 reviews)
"Book an oceanfront unit, the gentle sound of waves on the beach and the view from the patio or balcony is wonderful! Had a 1 brm suite that felt more like a condo-spacious & full kitchen. Daily texts from staff were helpful for requesting extra anything that we needed. And promptly brought to the ..."

Reviewed on Jul 6, 2026

Hilton Vacation Club Flamingo Beach St. Maarten
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Billy Folly Road No. 37A Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $397 per night from Aug 3 to Aug 4
CA $397
CA $487 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (1,447 reviews)
"Stayed for 4 days and had the breakfast included in our stay. It is in a location where you can walk to local shops and restaurants. Great experience."

Reviewed on Jul 5, 2026

The Villas at Simpson Bay Resort
See all 3,603 properties in Pelican Key
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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Beach Vacations
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Frequently asked questions

How much does a Pelican Key vacation package cost?
Discover the best of Pelican Key from as low as CA $1,109. We offer a wonderful selection of flights, rental cars and hotels to suit your budget. Score even more discounts when you add a few tours or experiences to your vacation package.
How do I get a cheap travel package to Pelican Key?
Simply by bundling. Flights, hotels and rental cars — combine whatever you need into a Pelican Key vacation package and save. Score even more deals when you include extras such as tours or experiences to your booking. But that's not the only good part. You have the flexibility to tailor your vacation your way. We offer over 550 air carriers and 1,000,000 hotels across the globe, so that everyone has a chance to travel and live out those vacation dreams.
Where should I stay in Pelican Key?
With interesting attractions such as Simpson Bay Beach and Flamingo Beach in this area, look for a hotel situated near either of them. Hollywood Casino is another Pelican Key hot spot that people flock to.
What are the top hotels in Pelican Key?
Get your vacation off to a fantastic start by booking a room at Sol Y Mar 3 Bedroom Villa By Redawning. It's one of most popular properties in Pelican Key. Another option is Pelican Key Private Luxury Villa With Panoramic View Of The Caribbean Sea.
How far in advance should I book my Pelican Key vacation?
Smart travelers often reserve their seats as early as possible. You can usually compare international fares on Expedia up to a year before your flight. If you've left things to the last minute, don't worry. Cheap prices sometimes occur just weeks prior to departure.
What does an Expedia Pelican Key travel package include?
You can select from a combination of rental cars, hotels and flights. Once you've made your booking, you can add activities and experiences. Want to pick your airfare class? That's easy to do too. The choice is all yours when it comes to arranging your ideal Pelican Key escape.
What should I know before booking a Pelican Key travel package?
You'll save plenty with an Expedia travel package. Bundle your airfares, rental cars and hotels and enjoy exciting discounts. Hotels aren't your only choice, though. Book with us and choose from beach villas, rural cottages and even houseboats and castles!
Can I choose my airline with a Pelican Key Expedia vacation package?
You certainly can. Expedia has access to more than 550 partner airlines worldwide, so pick the carrier that suits your travel needs.
If I'm not able to travel, can I cancel my Pelican Key vacation package?
Yes, you can. We get that things don't always go to plan, so we're here to help if you have to make changes to your Pelican Key vacation package. You may be able to change or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.

Stay near popular Pelican Key attractions

Hollywood Casino

8.2/10 (583 reviews)
Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.
See properties

Things to do

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $92
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $121
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $115
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
See all activities in Simpson Bay
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.