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.
The Villas at Simpson Bay Resort
Pelican Key
CA $1,776
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,507 reviews)
Room was clean and spacious. A bit outdated but well-maintained. Cleaned daily. Good linen. Thick white towels. Beautiful view.
Staff was friendly & helpful. Chad at Bovin Steakhouse gave THE best service!
Reviewed on Aug 25, 2026
Holland House Beach Hotel
Downtown Philipsburg
CA $1,661
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
The reviews that I saw which led me to book the hotel must have been falsified because the stay at this property was a nightmare. The staff especially the bellmen were unhelpful and at times seemed annoyed with simple requests. There’s no parking available so be prepared to play musical chairs while waiting for someone to let you in and out of the parking lot. The manager tried to rectify the issues on the last night of our stay. By then, the trip had already tanked- if you want peace of mind, hospitality and a seamless stay DO NOT BOOK THIS HOTEL.
Reviewed on Aug 24, 2026
Coral Beach Club Villas & Marina
Oyster Pond
CA $3,348
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (119 reviews)
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.
Reviewed on Jul 19, 2026
The Forest
CA $1,951
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
10/10 Exceptional! (26 reviews)
What a wonderful stay!! The staff was exceptional and accommodating the entire trip. The rooms were clean and very beautiful, not to mention the landscaping and the ease of getting to and from. I will most certainly be back!! Thank you!!!
Reviewed on May 11, 2026
Pelican Key Hotel Deals
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
CA $198
CA $242 total
Sep 23 - Sep 24
includes taxes & fees
9/10 Wonderful! (1,981 reviews)
"Nice property, convenient location!"
Reviewed on Aug 25, 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 $166
CA $211 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,736 reviews)
"Ok"
Reviewed on Aug 25, 2026
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A Simpson Bay
Fully refundableReserve now, pay when you stay
CA $239
CA $295 total
Sep 13 - Sep 14
includes taxes & fees
9.2/10 Wonderful! (1,521 reviews)
"Room was clean and spacious. A bit outdated but well-maintained. Cleaned daily. Good linen. Thick white towels. Beautiful view. Staff was friendly & helpful. Chad at Bovin Steakhouse gave THE best service!"
Reviewed on Aug 25, 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 $1,375. 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
Tango Sunset Cruise with Caribbean Dinner & Open Bar
CA $120
per adult
94% of travellers recommend
High-Speed Ferry to St. Barths
CA $114
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.