Chokoloskee Island

Travel Guide

A night sky with the Milky Way over a calm body of water and a rocky shoreline with wooden posts.
A dock with boats, a small white building, and people by the water.
A wooden boardwalk leading through a forested area with a sunset sky.
A forested path surrounded by dense green foliage and trees.
A sunset over a body of water with two islands silhouetted against the sky.
Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL
Stay at this beach holiday home in Chokoloskee. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Smallwood Store and Chokoloskee Bay are located ...
9.8/10 Exceptional! (65 reviews)
"This is an amazing spot! Perfect for a fishing trip or if you just want to get away from it all and experience old Florida. The views and access to the water can’t be beat. The house was clean, comfortable and well stocked. Lynn is a great, communicative, friendly host who made it easy. I hope to ..."

Reviewed on 19 Jul 2026

Get rates
Deep Water Access with a Panoramic View of Chokoloskee Bay
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

Chokoloskee FL
Stay at this holiday home in Chokoloskee. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Smallwood Store and Chokoloskee Bay are located ...
Get rates
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Waterfront 2 bedroom 1 bath with boat slip

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL
Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
10/10 Exceptional! (54 reviews)
"Place was spotless and nicely decorated. Great location for fishing. Great hospitality. Thanks for a great stay"

Reviewed on 24 May 2026

Get rates
Waterfront 2 bedroom 1 bath with boat slip
See all 198 properties in Chokoloskee Island
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.
Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL
Stay at this beach holiday home in Chokoloskee. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Smallwood Store and Chokoloskee Bay are located ...
9.8/10 Exceptional! (65 reviews)
"This is an amazing spot! Perfect for a fishing trip or if you just want to get away from it all and experience old Florida. The views and access to the water can’t be beat. The house was clean, comfortable and well stocked. Lynn is a great, communicative, friendly host who made it easy. I hope to ..."

Reviewed on 19 Jul 2026

Deep Water Access with a Panoramic View of Chokoloskee Bay
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

Chokoloskee FL
Stay at this holiday home in Chokoloskee. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Smallwood Store and Chokoloskee Bay are located ...
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Waterfront 2 bedroom 1 bath with boat slip

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL
Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
10/10 Exceptional! (54 reviews)
"Place was spotless and nicely decorated. Great location for fishing. Great hospitality. Thanks for a great stay"

Reviewed on 24 May 2026

Waterfront 2 bedroom 1 bath with boat slip
See all properties in Chokoloskee Island
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.

Stay near popular Chokoloskee Island attractions

Smallwood Store

You can spend time browsing the exhibits at Smallwood Store in Chokoloskee. You can seek out the fishing spots while in the area.
See properties

Explore a world of travel with Expedia