Pelican Key Vacations from $791
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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
Price was $1,423, price is now $791 per person
$791
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,007 reviews)
We loved this hotel for our family of 4. Lovely staff, unbeatable views/balcony, amazing fully stocked kitchen, delicious breakfast every morning, and wonderful pool too! This place had it all.
We loved the location too - ideal to get to beaches on both sides with a rental car.
Thank you for a very memorable stay!
Reviewed on Mar 21, 2026
Simpson Bay Resort, Marina & Spa
Pelican Key
Price was $2,251, price is now $958 per person
$958
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9/10 Wonderful! (1,629 reviews)
Omg! Sint Marteen was AMAZING the resort, PERFECT! Staff were so nice & friendly! They kept me laughing. The stay was so comfortable. I would stay here EVERY TIME! I absolutely loved it! 10/10 HIGHLY RECOMMEND!
Reviewed on Mar 19, 2026
The Villas at Simpson Bay Resort
Pelican Key
Price was $2,768, price is now $1,200 per person
$1,200
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.2/10 Wonderful! (1,387 reviews)
Nice room. Great view. Staff could be a bit friendlier overall - at the bar, beach staff putting out chairs, etc. overall nice stay
Reviewed on Mar 22, 2026
La Playa Orient Bay
Save 100% on your flight
Price was $1,706, price is now $999 per person
$999
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.4/10 Exceptional! (668 reviews)
The hotel location is excellent to walk everywhere - beach, restaurants, shops. The staff is friendly, professional and knowledgeable, especially Elena. The room was spacious, clean and had everything you need for a relaxing beach vacation. The breakfast is improved from last year and has more options to choose from. The restaurant staff could improve in greeting clients and restaurant cleanness.
Reviewed on Mar 18, 2026
Panorama Residences at Monte Vista
Point Blanche
Save 100% on your flight
Price was $2,057, price is now $1,224 per person
$1,224
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
9.6/10 Exceptional! (29 reviews)
The hotel is just built, excellent design, fully equipped, great ocean view, shops are 12 minutes drive.
Note that the hotel is located on top of the mountain and the access is very steep road about 1 mile, also the offered concierge service is not satisfactory.
Reviewed on Mar 19, 2026
Pelican Key Hotel Deals
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
$283 nightly
The price is $297 total per night from Apr 21 to Apr 22
$297 total
Apr 21 - Apr 22
Total with taxes and fees
8.8/10 Excellent! (1,632 reviews)
Omg! Sint Marteen was AMAZING the resort, PERFECT! Staff were so nice & friendly! They kept me laughing. The stay was so comfortable. I would stay here EVERY TIME! I absolutely loved it! 10/10 HIGHLY RECOMMEND!
Reviewed on Mar 19, 2026
The Villas at Simpson Bay Resort
Billy Folly Road No. 37A Simpson Bay
$361 nightly
The price is $379 total per night from Apr 21 to Apr 22
$379 total
Apr 21 - Apr 22
Total with taxes and fees
9.2/10 Wonderful! (1,380 reviews)
Nice room. Great view. Staff could be a bit friendlier overall - at the bar, beach staff putting out chairs, etc. overall nice stay
Reviewed on Mar 22, 2026
La Vista Hotel
Billy Folly Road Simpson Bay Sint Maarten
$280 nightly
The price is $295 total per night from Mar 30 to Mar 31
$295 total
Mar 30 - Mar 31
Total with taxes and fees
9.8/10 Exceptional! (44 reviews)
Very nice stay at La Vista. We will be back. Thank you!
Reviewed on Mar 20, 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.
Discover the most popular places to visit in Pelican Key
Hollywood Casino
Bingo, a handful of gambling tables, buffets and piano bars entertain the public at this almost intimate gambling hall.
Kim Sha Beach
Why not spend a carefree afternoon at Kim Sha Beach during your travels in Simpson Bay? Check out the shops and lively bars in this romantic area.
Lay Bay Beach
Why not spend a lazy afternoon at Lay Bay Beach during your trip to Simpson Bay?
Things to do
Sint Maarten: World's First Caribbean Carnival Experience
$40
per adult
100% of travellers recommend
Edge Ferry Tickets to St. Barts
$100
per adult
84% of travellers recommend
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- Flights to Simpson Bay
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- Car rentals near Paradise Plaza
- Car rentals near Simpson Bay
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- Car rentals near Cole Bay
- Car rental Simpson Bay Airport (SXM)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.