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 $528

Book a Hotel + Flight or Car together to unlock savings

The Latest Chokoloskee Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel lobby with a large chandelier, green walls, and a view of palm trees through the glass doors.
    Jan 20 - Jan 24

    Cavalier Hotel South Beach + Flight

    South Beach
    4 nights
    3.5 star property
    8.6/10 - Excellent (1,002 reviews)
    "I loved that it was an unique property & easily accessible to everything."
    Reviewed November 5, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop FLL - BOS • Nonstop
    $1,056
    $528
    per traveler
    found 1 day ago
    Cavalier Hotel 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
    $1,555
    $769
    per traveler
    found 1 day ago
    501 First Studio Balcony by Palermo Home
  • 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 1 day ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • A modern hotel room with a sofa, a small table with a telephone, a desk with a lamp, a bed with patterned bedding, a TV on the wall, and a large window with a city view.
    Dec 16 - Dec 19

    Avi Lux Stay + Flight

    East Fort Lauderdale
    3 nights
    4.5 star property
    7.6/10 - Good (10 reviews)
    "If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE. "
    Reviewed August 28, 2025
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • 1 stop MIA - BOS • 1 stop
    Save 100% on your flight
    $1,152
    $588
    per traveler
    found 1 day ago
    Avi Lux Stay
  • A room with a decorative bookcase filled with various items, a wicker chair, a cushioned sofa, and a framed artwork on the wall.
    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 1 day ago
    Henrosa Hotel

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.
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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.