A night sky with the Milky Way over a calm body of water and a rocky shoreline with wooden posts.
Photo by Noel Benadom
Open Photo by Noel Benadom

Chokoloskee Island Vacations from $573

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The Latest Chokoloskee Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with two single beds, a window with blinds, a bedside table with a lamp, and a wall with patterned wallpaper.
    Feb 3 - Feb 7

    Henrosa Hotel + Flight

    South Beach
    4 nights
    3.5 star property
    8.4/10 - Very good (963 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop FLL - BOS • Nonstop
    $1,097
    $573
    per traveler
    found 2 days ago
    Henrosa Hotel
  • A modern hotel with multiple floors, large windows, and a pool area.
    Jan 21 - Jan 24

    Hotel AKA West Palm + Flight

    Downtown West Palm Beach
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,393 reviews)
    "all in all a great place with attentive staff, comfortable accommodation, great area and beautiful surroundings."
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Fort Lauderdale (FLL)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $1,355
    $655
    per traveler
    found 1 day ago
    Hotel AKA West Palm
  • A poolside area with lounge chairs, a table with a beverage, and a view of the ocean.
    Jan 14 - Jan 17

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    3 nights
    5.0 star property
    8.0/10 - Very good (1 review)
    "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...."
    Reviewed June 22, 2016
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $15,567
    $7,805
    per traveler
    found 2 days ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • A modern living room with a large window, a flat-screen TV, a potted plant, a candle, and a view of a city skyline.
    Jan 16 - Jan 21

    501 First Studio Balcony by Palermo Home + Flight

    Downtown Miami
    5 nights
    2.0 star property
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $1,532
    $770
    per traveler
    found 2 days ago
    501 First Studio Balcony by Palermo Home
  • A modern hotel room with a large bed, a desk with a flat-screen TV, a glass partition, and a view of the outdoors.
    Jan 22 - Jan 28

    President Hotel Villa + Flight

    South Beach
    6 nights
    3.5 star property
    8.4/10 - Very good (1,000 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop FLL - BOS • Nonstop
    Save 100% on your flight
    $1,264
    $654
    per traveler
    found 2 days ago
    President Hotel Villa

Discover the most popular places to visit in Chokoloskee Island

Smallwood Store

You can spend time exploring the galleries in Smallwood Store during your trip to Chokoloskee. You can seek out the fishing spots while in the area.
See properties

Chokoloskee Island Hotel Deals

A modern hotel room with a bed, a sofa, a TV, a desk, and a wardrobe.

Everglades Adventures Hotel Suites by Ivey House

Everglades Adventures Hotel Suites by Ivey House
2.5 star property
4 mi from Chokoloskee Island
9.2 out of 10, Wonderful, (1,007 reviews)
"Very nice staff. Room was large and we had everything we needed. Would definitely recommend"
$109 nightly
The price is $121
Dec 1 - Dec 2
Total with taxes and fees
Everglades Adventures Hotel Suites by Ivey House
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 Chokoloskee Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.