
Chokoloskee Island Vacations from $468
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The Latest Chokoloskee Island vacation packages
Price found within the past 48 hours. Click for updated prices.

The Perry Hotel Naples
Save 100% on your flight
Price was $713, price is now $468 per person
$468
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (748 reviews)
Strongly suggest the shuttle it takes you out to a secluded beach area!! The hotel, in my opinion is perfectly located. Close to shops, restaurants, and walking trails. Vanderbilt Beach area is close by car but far enough away if you’d rather not deal with the congestion.
Reviewed on Apr 13, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,305, price is now $693 per person
$693
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,002 reviews)
Excellent location and hotel!
Reviewed on Apr 12, 2026

Matanzas Inn Bayside Resort and Marina
Save 100% on your flight
Price was $809, price is now $518 per person
$518
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,008 reviews)
We enjoyed our stay! Very convenient location, right on the water, clean with recently renovated rooms. We went for a girls weekend and loved it! The only thing I can’t rave about was they had very poor water pressure, not sure if it was because we were on an end unit, but it was a trickle out of the shower head which can be a little difficult if you have a lot of hair, no hairdryer in room, and wish they had a full sized mirror in the room. Regardless I would definitely recommend staying there! It’s a beautiful property!
Reviewed on Apr 14, 2026

Edison Beach House
Save 100% on your flight
Price was $786, price is now $505 per person
$505
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,702 reviews)
We had a great time at Edison Beach House! A clean, kind, well cared for place with kind people working all areas! We were impressed by the kitchen amenities, and the ease of check in! We absolutely recommend! Our view was beautiful and we hope to come back again! Catching the sunset and sunrise each day was amazing!
Reviewed on Apr 16, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $959, price is now $643 per person
$643
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (821 reviews)
spectacular place for a weekend!!
Reviewed on Apr 16, 2026
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Deep Water Access with a Panoramic View of Chokoloskee Bay
Chokoloskee FL
9.8/10 Exceptional! (63 reviews)
Had a great time in Chokoloskee, exploring the area by boat. We had our own small boat, and we launched it and kept it at the dock while staying at this beautiful home on the water. We had some great fishing, even though unfamiliar with that part of the water in Florida. It does get shallow, so smaller ...
Reviewed on Mar 31, 2026

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

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park
Chokoloskee FL
9.6/10 Exceptional! (9 reviews)
The property is as advertised. The RV has a few miles on it, but was clean and everything worked. One sleeping area has a great view of the Glades. The porch is covered and also faces the Park. Boat slip has easy access to the Everglades and there is spacious parking for boat trailer and vehicle(s). ...
Reviewed on Mar 24, 2026
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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