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.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,762, price is now CA $1,119 per person
CA $1,119
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
9.6/10 Exceptional! (912 reviews)
The room was very specious but the shower could’ve been cleaner as it has moldy edges. The restaurants were good but not enough options for kids. The staff were always very helpful and kind.

Reviewed on Jul 6, 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 $2,851, price is now CA $1,843 per person
CA $1,843
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
9/10 Wonderful! (1,009 reviews)
We had a pleasant stay , The kids had a blast the beach service was great the staff was very friendly. the room were beautiful very happy with our choice .!

Reviewed on Jul 6, 2026

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $2,383, price is now CA $1,638 per person
CA $1,638
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,005 reviews)
Great location! Overall, room was clean and there was no carpet (which is a plus for us). Pool is small but very enjoyable!

Reviewed on Jul 6, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was CA $2,158, price is now CA $1,529 per person
CA $1,529
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
We had a lovely stay. I do feel it was somewhat overpriced. The previous week was priced $100 cheaper and I think that would be more appropriate. The rooms are very nice but not exceptionally luxurious and oh that cheap shampoo was brutal. Please, please provide conditioner!! Overall though it was really charming and we had a wonderful time. Shout-out to the coffee girl who decorated every cup. That was delightful.

Reviewed on Jul 1, 2026

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Price was CA $2,581, price is now CA $1,845 per person
CA $1,845
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
9.6/10 Exceptional! (2,285 reviews)
All in all it was excellent. The elevator to our third floor was smelly, could not pinpoint smell

Reviewed on Jul 5, 2026

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Chokoloskee Hotel Deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

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

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

Chokoloskee FL
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The Reel'em Inn, Chokoloskee Island Fisherman's Paradise
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

Ochopee FL
9.8/10 Exceptional! (21 reviews)
"Great host"

Reviewed on May 23, 2026

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Waterfront Everglades basecamp with dock, trailer parking, and direct bay access
See all 216 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 $152
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 $166
per adult
100% of travellers recommend
Everglades Birding, Dolphin and Wildlife Boat Tour (2 hours)
Everglades NP and Big Cypress NP Self Guided Driving Tour Bundle

Everglades NP & Big Cypress App-Based Driving Tour Bundle

CA $35
per traveller
Everglades NP & Big Cypress App-Based Driving Tour Bundle
See all activities in Chokoloskee

Frequently asked questions

How much does a Chokoloskee vacation package cost?
You'll find cheap prices from CA $1,119 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.

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