Pelican Key Vacation Packages 2026 from $692

Plan, book, travel with confidence
Better together
Save up to $2,000 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

Your Pelican Key Vacation

Whether you're coming for its coastal beaches or views, the neighborhood of Pelican Key has plenty to keep you entertained. Uncover all of this and more with ease by booking a Pelican Key vacation package. Start your trip to Pelican Key by heading to nearby attractions such as Simpson Bay Beach, Flamingo Beach and Hollywood Casino. No matter what your ideal Pelican Key vacation looks like, you can turn it into reality with Expedia.

The Latest Pelican Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$692

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,000 reviews)

The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.

Reviewed on Sep 14, 2026

The Villas at Simpson Bay Resort

Pelican Key

$825

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,549 reviews)

Simpson Bay Resort, Marina & Spa

Pelican Key

$1,127

per person

Nov 25 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)

9/10 Wonderful! (2,057 reviews)

The Morgan Resort Spa Village

Save 100% on your flight

$1,062

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (2,409 reviews)

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Save 100% on your flight

$1,507

per person

Nov 17 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

8/10 Very Good! (3,224 reviews)

Everything was great

Reviewed on Sep 24, 2026

Pelican Key Hotel Deals

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

Fully refundableReserve now, pay when you stay

$183 nightly

$191 total

Oct 12 - Oct 13

Total with taxes and fees

The Villas at Simpson Bay Resort

Billy Folly Road No. 37A Simpson Bay

Fully refundableReserve now, pay when you stay

$206 nightly

$215 total

Oct 4 - Oct 5

Total with taxes and fees

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay

Fully refundableReserve now, pay when you stay

$147 nightly

$155 total

Oct 4 - Oct 5

Total with taxes and fees

9.2/10 Wonderful! (1,763 reviews)

"Close to everything."

Reviewed on Sep 25, 2026

See all 3,596 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.