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.
Simpson Bay Resort, Marina & Spa
Pelican Key
CA $2,929
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
We loved the resort. There’s something for everyone there. The restaurants were great, Laura at the pool bar was awesome . The workers were always at work cleaning the property . It was so clean .
Everyone there made you feel like family even the guests we met at the pool, at the restaurants, by the beach .
I’ve never felt more welcomed. Not pushy people either just happy pleasant people.
There was a grocery store right on the property too which made it
We stayed right on the beach in an ocean front room .we had a patio to sit outdoors .
Reviewed on Oct 10, 2026
The Villas at Simpson Bay Resort
Pelican Key
CA $2,142
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
Loved it all complimentary bottle of Chilean wine. We had an ocean/pool view one bedroom villa and just loved it. Absolutely loved the staff especially Monique who had amazing dinner recommendations for us at her fingertips. Ask for her! 10/10
Reviewed on Oct 9, 2026
Pelican Key Hotel Deals
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
CA $186
per night
Oct 17 - Oct 18
9/10 Wonderful! (2,099 reviews)
"Clean spacious room. Lots to do and eat within walking distance."
Reviewed on Oct 9, 2026
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A Simpson Bay
Fully refundableReserve now, pay when you stay
CA $235
per night
Oct 19 - Oct 20
9.2/10 Wonderful! (1,577 reviews)
"Loved it all complimentary bottle of Chilean wine. We had an ocean/pool view one bedroom villa and just loved it. Absolutely loved the staff especially Monique who had amazing dinner recommendations for us at her fingertips. Ask for her! 10/10"
Reviewed on Oct 9, 2026
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
Fully refundableReserve now, pay when you stay
CA $157
per night
Oct 23 - Oct 24
9.2/10 Wonderful! (1,782 reviews)
"Clean room"
Reviewed on Oct 9, 2026
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.
Frequently asked questions
How much does a Pelican Key vacation package cost?
Discover the best of Pelican Key from as low as CA $1,287. 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.
Lay Bay Beach
8.4/10 (212 reviews)
Why not spend a lazy afternoon at Lay Bay Beach during your trip to Simpson Bay?
Things to do
Half Day Snorkeling Adventure
CA $91
per adult
100% of travellers recommend
Mambo Catamaran Cruise to Rendezvous Bay Anguilla with Lunch
CA $189
per adult
86% of travellers recommend
Guided UTV/ Side by Side Tour of Sint Maarten/ St. Martin
CA $420
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.