
Chokoloskee Island Vacations from $340
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The Latest Chokoloskee Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $556, price is now $340 per person
$340
per person
Apr 11 - Apr 16
found 2 days ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,001 reviews)
Hotel was clean and in a safe area. Pool was a key feature as it was heated and a decent size. Breakfast not included in rate but avail for $18. Room was quiet and updated. We had an issue with the bed fitted sheets coming off which we reported on day one. Same thing happened on days 2 and 3. Seems the fitted sheets are not king sized.
Reviewed on Mar 3, 2026

Matanzas Inn Bayside Resort and Marina
Save 100% on your flight
Price was $1,076, price is now $664 per person
$664
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Tidy room, easy access, good parking, great location.
Reviewed on Mar 2, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $711, price is now $456 per person
$456
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
The pools and Lazy river was awesome. Condos a little outdated but nice
Reviewed on Mar 3, 2026

The Perry Hotel Naples
Save 100% on your flight
Price was $919, price is now $597 per person
$597
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
Such a beautiful hotel! Both the rooftop and outside pool were heated and absolutely delightful! They have a boat that will take you down the river and drop you off at Barefoot Beach. You can stay as long as you like as boat comes back every hour. The food at the rooftop restaurant (The Tigress) was one of the best dinners we’ve had in a long time! Highly recommend this hotel! Will be coming back!
Reviewed on Mar 4, 2026

Hilton Marco Island Beach Resort and Spa
South End
Save 100% on your flight
Price was $1,197, price is now $797 per person
$797
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,714 reviews)
The Hilton is excellent, if one wants more updated decor this may not be for that traveler It meet the reds for this trip a sunshine break!
Reviewed on Mar 3, 2026
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Deep Water Access with a Panoramic View of Chokoloskee Bay
Chokoloskee FL
10/10 Exceptional! (60 reviews)
The location was amazing with the south facing house. You can watch the sunrise and the sunset. We didnt come to fish but we may be back tonfish. The Smallwood Store is a must visit.
Reviewed on Jan 1, 2026

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park
Chokoloskee FL
9.6/10 Exceptional! (7 reviews)
National park was very close fishin was amazing place was extremely clean and cozy I loved every second
Reviewed on Nov 20, 2025

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
Chokoloskee FL
9.6/10 Exceptional! (133 reviews)
Everything was fantastic. if we had any questions or any concerns, the owner responded right away and helped us out. we would have loved to stay longer, but unfortunately, Weather wasn’t on our side.. the people that were around that place were awesome very friendly polit…
Reviewed on Nov 30, 2025
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.
Find the Best Chokoloskee Island Vacation Packages
Chokoloskee Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Miami Intl. Airport (MIA) |
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