
Chokoloskee Island Vacation Packages
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Top Chokoloskee Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Courtyard by Marriott Fort Myers Cape Coral
Price was CA $1,327, price is now CA $823 per person
CA $823
per person
Mar 24 - Mar 31
found 21 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Fort Myers (RSW)
8.2/10 Very Good! (997 reviews)
Very clean room. Could use better pillows.
Reviewed on Feb 3, 2026

Matanzas Inn Bayside Resort and Marina
Price was CA $2,083, price is now CA $1,041 per person
CA $1,041
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Room was clean. Front staff was excellent at her job.
Reviewed on Feb 5, 2026

Marriott Sanibel Harbour Resort & Spa
Punta Rassa
Price was CA $2,652, price is now CA $1,711 per person
CA $1,711
per person
Mar 24 - Mar 31
found 21 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Fort Myers (RSW)
8.4/10 Very Good! (1,005 reviews)
Nice room and perfect location
Reviewed on Feb 1, 2026

South Seas Resort
Price was CA $2,587, price is now CA $1,679 per person
CA $1,679
per person
Apr 23 - Apr 27
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.4/10 Very Good! (1,001 reviews)
I'll preface this by saying that i had an incredible week and rhat Captiva is literal Paradise. My lodging however could use some work. The main office, gym facility, and retail establishments are excellent. Unfortunately my actual suite could use some work. While the facility was clean and had a spectacular view- the lodging was old and tired. Dirty elevators cheaply updated should have been a sign of things to come. Once inside the lodging I found cheap plastic flooring that flexed as you walked over uneven surface underneath. The walls were "updated" with textured wall covering the in areas was peeling. Baseboard looked as if a child did.the job. Poorly finished, improperly cut, and nailholes unfinished. Most things painted revraled many layers of old paint. Nights 1 and 2 were spent listening to the toilet by the bedroom run. Despite requesting it be remedied- it took speaking to the property manager on day 3 to get this accomplished. Ironically, the second toilet also broke and needed repair. Additionally- the water was only "warm" in the shower. Dining at the "resort" facilities is ridiculously expensive, so I ate better elsewhere for the same price. Lastly, there's no hospitality all week. You make your own bed, hang your towels, and if you want more- you drive to get them yourself.
Reviewed on Jan 18, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Price was CA $1,444, price is now CA $953 per person
CA $953
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.8/10 Exceptional! (1,027 reviews)
La suite a surpassé nos attentes. Propreté impeccable. Équipée de tout ce dont on avait besoin. La vue sur la plage était charmante. La grandeur de l’unité était parfaite. Nous aurions pu y être 4 sans se sentir à l’étroit. Le personnel est très aidant et généreux. C’est un endroit paradisiaque.
Reviewed on Feb 3, 2026
Chokoloskee Island Hotel Deals

Deep Water Access with a Panoramic View of Chokoloskee Bay
Chokoloskee FL
9.8/10 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
9.4/10 Exceptional! (6 reviews)
National park was very close fishin was amazing place was extremely clean and cozy I loved every second
Reviewed on Nov 20, 2025

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise
Chokoloskee FL
10/10 Exceptional! (10 reviews)
Great property! Amazing hosts!
Reviewed on Aug 20, 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.
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