
Chokoloskee Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Chokoloskee Vacation
The fascinating city of Chokoloskee is calling. Discover all its secrets with a Chokoloskee vacation package that's custom made for you. If seeing the sights is a priority during your trip to Chokoloskee, make sure you find your way to popular attractions like Everglades City Hall and Museum of the Everglades. Your dream Chokoloskee vacation is a few clicks away. Browse airfares, hotels and more on Expedia for a trip that's tailored to suit your style.
Top Chokoloskee Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Marriott Sanibel Harbour Resort & Spa
Punta Rassa
Price was CA $1,508, price is now CA $1,054 per person
CA $1,054
per person
Jun 4 - Jun 9
found 9 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
8.4/10 Very Good! (1,013 reviews)
Really enjoyed our stay, rooms were clean and amenities were great!
Reviewed on Mar 23, 2026

Hilton Marco Island Beach Resort and Spa
South End
Price was CA $1,907, price is now CA $1,296 per person
CA $1,296
per person
Jun 4 - Jun 9
found 9 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
9/10 Wonderful! (1,726 reviews)
We were surprised by the fact that we paid a lot for this hotel/ room and had to request robes although they were supposed to be in our room, the cups were plastic disposals, the balcony chairs were cheap, the room furnishings were a little run down, there wasn’t much room for our toiletries in the bathroom, and while there was a cheap little coffee maker in the room, we had to keep requesting the coffee supplies be replenished every day. Housekeeping didn’t clean the room until mid afternoon, and we had to ask for the sheets to be changed as we stayed for 10 nights and shouldn’t have had to ask for this. The A/C either blew so cold we needed an extra blanket or didn’t get cold enough at a lowered setting because the system switched to heat if we set it at72 degrees. The restaurant was also disappointing in that it was cheaply decorated as well as the tables and chairs were cheap. The actual food was really good, the wait staff was awful. Then, on top of what you are charged for the room, there is an additional charge of 44$ a day to use beach chairs, towels, and an umbrella. Also, there’s a $40.00 per day parking fee on top of the resort charge. There was no one at the desk when we left at 7 AM. It’s ironic that we are big Formula 1 fans, and Lando Norris is the spokesperson for Hilton Hotels, and claims he always stays at Hilton… Lando wouldn’t stay here. And finally, I did reach out to Hilton via their website in an email, I have yet to hear any response after 2 weeks
Reviewed on Mar 25, 2026

Matanzas Inn Bayside Resort and Marina
Price was CA $1,724, price is now CA $1,219 per person
CA $1,219
per person
May 5 - May 10
found 16 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,021 reviews)
Tremendous value with a $.75 shuttle that takes you over the met Aunt’s past bridge in the heart of Fort Myers Beach
Reviewed on Mar 23, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was CA $1,479, price is now CA $1,063 per person
CA $1,063
per person
May 16 - May 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (803 reviews)
The property was very well maintained and clean. The room was clean and well kept. We had a group of 8 and there was plenty of room within our two bedroom suite. The pool was great and the kids had a great time within the 5 pools. Service was great and the staff were super nice.
Reviewed on Mar 25, 2026
Chokoloskee Hotel Deals

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 2 bedroom 1 bath with boat slip
Chokoloskee FL

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.
What to do in Chokoloskee

Everglades: 2 hour Manatee, Dolphin & Birding Boat Tour
CA $151
per adult

Everglades NP & Big Cypress App-Based Driving Tour Bundle
CA $31
per traveller

Everglades Birding, Dolphin and Wildlife Boat Tour (2 hours)
CA $164
per adult
100% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







