A beach with thatched umbrellas, a pier, and boats in the background.

Pelican Key Vacations from $811

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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.
  • A breakfast table with croissants, a watermelon slice, and a glass of orange juice, overlooking the ocean.
    Dec 12 - Dec 16

    Princess Heights Luxury Boutique Condo Hotel + Flight

    Oyster Pond
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,001 reviews)
    "I loved the warm staff and the help they provided me during my stay"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    Save 100% on your flight
    $1,465
    $811
    per traveler
    found 1 day ago
    Princess Heights Luxury Boutique Condo Hotel
  • A resort with multiple hotel buildings, a marina, and a clear blue ocean.
    Jan 9 - Jan 13

    The Villas at Simpson Bay Resort + Flight

    Pelican Key
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,609 reviews)
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    $2,819
    $1,332
    per traveler
    found 2 days ago
    The Villas at Simpson Bay Resort
  • A beach with thatched umbrellas and lounge chairs, a palm tree, and a building in the background.
    Jan 9 - Jan 13

    Simpson Bay Resort, Marina & Spa + Flight

    Pelican Key
    4 nights
    4.0 star property
    9.0/10 - Wonderful (2,177 reviews)
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    $2,548
    $1,257
    per traveler
    found 2 days ago
    Simpson Bay Resort, Marina & Spa
  • A clear blue pool with lounge chairs and palm trees, overlooking the ocean.
    Jan 9 - Jan 13

    The Morgan Resort Spa Village + Flight

    Simpson Bay
    4 nights
    4.0 star property
    9.0/10 - Wonderful (2,423 reviews)
    "Quiet, close to many restaurants and fun things to do. We had a driver- highly recommended"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    $1,596
    $986
    per traveler
    found 2 days ago
    The Morgan Resort Spa Village
  • A modern pool area with a view of the ocean, surrounded by palm trees and lounge chairs.
    Jan 9 - Jan 13

    Panorama Residences at Monte Vista + Flight

    Point Blanche
    4 nights
    4.5 star property
    9.6/10 - Exceptional (105 reviews)
    "Super clean, beautiful location. Friendly staff. Safe place. Will book again"
    Reviewed October 24, 2026
    Roundtrip • Boston (BOS) - Saint Martin (SXM)
    BOS - SXM • 1 stop SXM - BOS • 1 stop
    $1,845
    $1,143
    per traveler
    found 2 days ago
    Panorama Residences at Monte Vista

Discover the most popular places to visit in Pelican Key

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.
See properties

What to do near Pelican Key

Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

$65
per adult
100% of travelers recommend
Half Day Snorkeling Adventure
See all activities near Pelican Key

Pelican Key Hotel Deals

A resort with multiple hotel buildings, a marina, and a clear blue ocean.

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort
4.0 star property
Pelican Key
9.2 out of 10, Wonderful, (1,609 reviews)
$271 nightly
The price is $283
Nov 15 - Nov 16
Total with taxes and fees
The Villas at Simpson Bay Resort
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.
See all properties in Pelican Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.