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 $697

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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 28 - Feb 2

    Cavalier Hotel South Beach + Flight

    South Beach
    5 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 MIA - BOS • Nonstop
    $1,317
    $697
    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
    $1,545
    $765
    per traveler
    found 1 day ago
    501 First Studio Balcony by Palermo Home
  • 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.
    Jan 20 - Jan 24

    Avi Lux Stay + Flight

    East Fort Lauderdale
    4 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 • Nonstop FLL - BOS • Nonstop
    $1,396
    $725
    per traveler
    found 1 day ago
    Avi Lux Stay
  • A hotel room with a large window offering a city view, a bed, a tray with croissants, strawberries, a glass of orange juice, and a cup.
    Jan 28 - Feb 3

    Miami Vacation Rentals - Downtown + Flight

    Downtown Miami
    6 nights
    5.0 star property
    9.0/10 - Wonderful (125 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop MIA - BOS • Nonstop
    $2,547
    $1,339
    per traveler
    found 1 day ago
    Miami Vacation Rentals - Downtown
  • A spacious living area with a large window overlooking the sea, a sofa set, a dining table, and a potted plant.
    Jan 28 - Feb 3

    72 Park Miami Beach Boutique Residences by IliosRentals + Flight

    North Beach
    6 nights
    4.5 star property
    8.2/10 - Very good (19 reviews)
    "We had a wonderful stay with our group of three adults and three children! Everything was very comfortable, and the apartment was beautiful, clean, and well-maintained. There is a convenient shuttle service to the beach, but the 10-minute walk is also perfectly fine, even with children. Communication was excellent, and any questions we had were answered quickly. Overall, a very pleasant experience for the whole family. We would definitely recommend this place and would happily stay here again!"
    Reviewed October 17, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop MIA - BOS • Nonstop
    $2,594
    $1,391
    per traveler
    found 1 day ago
    72 Park Miami Beach Boutique Residences by IliosRentals

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.