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.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $1,959, price is now CA $1,242 per person
CA $1,242
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,004 reviews)
The staff and room were excellent. The daily breakfast was wonderful. The BEST croissants anywhere!! It was nice to have the guest laundry; the appliances need to be updated though. The only thing we can think of is a propane bbq(s) would be very much appreciated. Charcoal takes much too long to wait be fire you can cook your meal. Thank you PH for a fantastic stay.

Reviewed on Jun 18, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $3,805, price is now CA $1,800 per person
CA $1,800
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,426 reviews)
Overall the staff was excellent. Winston was very helpful in getting my room changed out. Only thing I would like to see area rugs for when the floor is cold. Maybe update the bedding and curtains. But Overall I would stay again.

Reviewed on Jun 19, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $3,083, price is now CA $1,533 per person
CA $1,533
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,780 reviews)
Limpieza restaurante piscina playa

Reviewed on Jun 19, 2026

Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $1,892, price is now CA $1,306 per person
CA $1,306
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
The FREE happy hour drinks on the patio with live music was unexpected and amazing!

Reviewed on Jun 11, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $3,057, price is now CA $2,124 per person
CA $2,124
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,214 reviews)
This property is beautiful. The staff was helpful. The outdoor pool is clean. The view is amazing.

Reviewed on Jun 18, 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 $324 per night from Jun 24 to Jun 25
CA $324
CA $397 total
Jun 24 - Jun 25
includes taxes & fees
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
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 3 to Jul 4
CA $155
CA $200 total
Jul 3 - Jul 4
includes taxes & fees
9.2/10 Wonderful! (1,595 reviews)
"Have been going to the Flamingo before it was purchased by Hilton. Hilton did a nice job on the rebuild after hurricane Irma. Room was clean except floor always had sand on it. Staff did bare minimum on checkin, checkout. They did not share much information unless asked. On check out they stated ..."

Reviewed on Jun 18, 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 $414 per night from Jul 12 to Jul 13
CA $414
CA $508 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (1,417 reviews)
"Overall the staff was excellent. Winston was very helpful in getting my room changed out. Only thing I would like to see area rugs for when the floor is cold. Maybe update the bedding and curtains. But Overall I would stay again."

Reviewed on Jun 19, 2026

The Villas at Simpson Bay Resort
See all 3,590 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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Frequently asked questions

How much does a Pelican Key vacation package cost?
Discover the best of Pelican Key from as low as CA $1,242. 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.

Discover the most popular places to visit in Pelican Key

Hollywood Casino

Hollywood Casino

Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.

Hollywood Casino
Kim Sha Beach

Kim Sha Beach

Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and top-notch restaurants in this romantic area.

Kim Sha Beach

Things to do

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

CA $90
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

CA $118
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 $103
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.