Photo by Noel Benadom
Plan, book, travel with confidence
Better together
Save up to CA $775 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Chokoloskee Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Inn on Fifth
Old Naples
Save 100% on your flight
per person
Aug. 1 - Aug. 5
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
I like the complimentary shuttle service. However, it wasn't always available at a moment's notice. The wait would have been 15 min. Too much cash spent on tipping. The 5 days we stayed were records breaking temperatures, so shuttle service was nice. The front desk staff were all very friendly. Requests for extra hangers and housekeeping service were courteous and prompt. 2 complementary water bottles each day were provided. Great experience using the soft water shower; however, lights would turn off while taking shower, and had to open the shower door to turn it on again. Bed and linens were comfortable.
Reviewed on Jun. 3, 2024
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
per person
Aug. 12 - Aug. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (1,000 reviews)
Very very expensive. Food and alcohol are very expensive here. For being a beach resort the tiki bar closed at 8:00 pm everyday even on the weekend. The inside bar closed at 10:00.
Reviewed on Jun. 3, 2024
Naples Grande Beach Resort
Park Shore
Save 100% on your flight
per person
Aug. 15 - Aug. 20
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,182 reviews)
We had a great time at the resort! Family friends, clean, safe and beautiful! We definitely will be back god willing!
Reviewed on Jun. 4, 2024
The Boat House
Save 100% on your flight
per person
Aug. 15 - Aug. 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (502 reviews)
We couldn’t have been more impressed with The Boat House. Though the property is older, the rooms are HUGE, spotlessly clean and beautifully updated. Everything was lovely and it was very reasonably priced. The staff was so kind and accommodating. Beautiful view of the water from the dock. We will recommend and stay again without a doubt. We walked to dinner and breakfast as well. Thank you for such a delightful stay!
Reviewed on Jun. 2, 2024
Chokoloskee Island Hotel Deals
Deep Water Access with a Panoramic View of Chokoloskee Bay
Chokoloskee
10/10 Exceptional! (47 reviews)
Great place, Great people
"Wonderful place to stay. LM and GM are great hosts. Place was immaculate and sitting out at night looking at the oyster bars is an amazing experience. Choko is one of the last real Florida experiences left and this property exemplifies it. Thanks again!"
Reviewed on Apr. 8, 2024
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
Chokoloskee
9.4/10 Exceptional! (110 reviews)
Old school Florida
"Wanted to bring the family down to experience the wilds of the Everglades and spend some time in a part of Florida that hadn’t been turned into a tourist trap. Chokoloskee and Big Blue came through spectacularly. The natural beauty and experiences here are something that will always stick with us. ..."
Reviewed on Apr. 1, 2024
Waterfront 2 bedroom 1 bath with boat slip
Chokoloskee
9.8/10 Exceptional! (34 reviews)
Fishing getwaway
"Awesome place, very clean and well equipped. Probably the nicest and most accommodating hosts we have experienced so far We definitely plan to be back"
Reviewed on May 29, 2024
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.
Frequently asked questions
Discover the most popular places to visit in Chokoloskee Island
Everglades National Park
This sprawling wetland park holds a seemingly endless supply of wildlife habitats and enthralling ecosystems.
Big Cypress National Preserve
4.5/5(6 reviews)
Explore the great outdoors at Big Cypress National Preserve, a lovely green space in Ochopee. While you're in the area, stroll along the lakeside.
Fakahatchee Strand Preserve State Park
Enjoy the beautiful sunsets and explore Fakahatchee Strand Preserve State Park, a lovely green space in Naples. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.
Other vacations you might like
Hotels
Flights
Activities
Packages
Vacation Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.