Chokoloskee Vacation Packages

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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.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was CA $2,290, price is now CA $1,415 per person
CA $1,415
per person
Dec 15 - Dec 22
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Fort Myers (RSW)
9.4/10 Exceptional! (135 reviews)
Beautiful location.

Reviewed on Nov 8, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $6,803, price is now CA $4,402 per person
CA $4,402
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)

GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
South Island
Save 100% on your flight
Price was CA $2,841, price is now CA $1,904 per person
CA $1,904
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (982 reviews)
Beautiful property, generous size condos and all the amenities.

Reviewed on Nov 6, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $2,148, price is now CA $1,498 per person
CA $1,498
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (1,224 reviews)

Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was CA $2,178, price is now CA $1,538 per person
CA $1,538
per person
Jan 9 - Jan 16
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9.8/10 Exceptional! (31 reviews)
And easy check-in. Brittany made the process seamless.

Reviewed on Nov 9, 2026

Ready to book your vacation to Chokoloskee?

 

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Chokoloskee Hotel Deals

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

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

Chokoloskee FL
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
10/10 Exceptional! (56 reviews)
"We had a wonderful and comfortable stay"

Reviewed on Nov 5, 2026

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Waterfront 2 bedroom 1 bath with boat slip
Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Chokoloskee FL
9.6/10 Exceptional! (12 reviews)
"The listing was very accurate and the property matched the photos. The host provided the location and check in information in a timely manner. Relaxation was the name of our game and the neighborhood was quiet. Even though the property is aging the inside was in very good condition. A nice large ..."

Reviewed on Aug 9, 2026

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Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park
See all 217 properties in Chokoloskee
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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Stay near popular Chokoloskee attractions

Chokoloskee Bay

9.2/10 (148 reviews)
Commune with nature and explore the great outdoors at Chokoloskee Bay during your travels in Chokoloskee. Stroll along the marina in this relaxing area, or seek out the kayaking spots.
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What to do in Chokoloskee

Everglades National Park: 2 hour Dolphin & Birding Boat Tour

Everglades: 2 hour Manatee, Dolphin & Birding Boat Tour

CA $155
per adult
Everglades: 2 hour Manatee, Dolphin & Birding Boat Tour
Everglades National Park Dolphin, Birding and Wildlife Boat Tour

Everglades Birding, Dolphin and Wildlife Boat Tour (2 hours)

CA $169
per adult
100% of travellers recommend
Everglades Birding, Dolphin and Wildlife Boat Tour (2 hours)
Small Group Motorboat Eco Tour of the Everglades

Small Group Motorboat Eco Tour of the Everglades

CA $210
per adult
Small Group Motorboat Eco Tour of the Everglades
See all activities in Chokoloskee

Frequently asked questions

How much does a Chokoloskee vacation package cost?
You'll find cheap prices from CA $1,415 on Expedia for your Chokoloskee escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Chokoloskee costs.
What are the cheapest months to go to Chokoloskee?
The off-season is the best time to head to Chokoloskee if you're on a budget. Another tip for getting cheap Chokoloskee vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Chokoloskee?
The ideal length for your Chokoloskee vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to check out all the leading attractions and explore some hidden spots along the way.
How to find the best Chokoloskee package deals?
Begin your search for a Chokoloskee package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chokoloskee package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chokoloskee adventure underway.
Is it cheaper to book a Chokoloskee vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking hotels and flights separately. Better still, you can customize your Chokoloskee escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chokoloskee?
Score incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chokoloskee escape.
How to plan a trip to Chokoloskee?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to vacation in Chokoloskee.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to airfares and activities. Your hotel will probably be the largest expense during your trip to Chokoloskee.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Chokoloskee. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, lock in the right Chokoloskee vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.