Chokoloskee Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

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 $1,533, price is now CA $1,074 per person
CA $1,074
per person
Sep 4 - Sep 8
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (893 reviews)

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 $2,155, price is now CA $1,422 per person
CA $1,422
per person
Sep 4 - Sep 8
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
We had an excellent stay at La Playa Beach & Golf Resort in Naples. The location is hard to beat—the hotel is right on a beautiful stretch of beach, making it incredibly convenient to enjoy the Gulf without ever needing to leave the property. The amenities were outstanding. We loved relaxing by the pool, the beach service was excellent, and everything was well maintained. The staff was friendly and attentive, helping make our stay feel truly relaxing and enjoyable. If you’re looking for a beachfront resort with great amenities and a wonderful atmosphere, La Playa is an excellent choice. We would definitely stay here again.

Reviewed on Jun 29, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was CA $1,761, price is now CA $1,173 per person
CA $1,173
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.2/10 Wonderful! (2,876 reviews)
Hotel is beautiful ,very clean,main pool is nice,front desk staff is polite.Food is expensive at food court,they always ask for 18% or 20% tip of everything even though they just hand you the food in a tray and you take it yourself to your table.Plenty of resort fees to be aware of,parking fees,I self parked all 3 days but they sneaked a valet fee of $36 on my bill I dont know why.Rooms do not block out sound at all,first night we had noisy neighbors at 3 am partying in the room accross.I had to contact front desk and they solved the issue though.There is nothing to do in Port Charlotte,is a ghost town.I checked out a day before,will definetly not come back.Not worth all the resort fees.

Reviewed on Jun 30, 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was CA $1,892, price is now CA $1,341 per person
CA $1,341
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (25 reviews)
very clean, very nice staff

Reviewed on Jun 30, 2026

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $2,599, price is now CA $1,844 per person
CA $1,844
per person
Aug 3 - Aug 10
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,005 reviews)
Our room was amazing. Very spacious and clean. The hotel is located in the middle of everything. Parking is OK. There is a parking garage a block or 2 away. We would definitely stay again.

Reviewed on Jun 27, 2026

Ready to book your vacation to Chokoloskee?

 

Choose your dates

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
Get rates
Deep Water Access with a Panoramic View of Chokoloskee Bay
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Chokoloskee FL
9.6/10 Exceptional! (135 reviews)
"Great place for stay with my family, first time on Chokoloskee and Everglades City and we enjoy it all the time, we definitely will stay here again. Thank you"

Reviewed on May 25, 2026

Get rates
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

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

Ochopee FL
The price is CA $316 per night from Jul 6 to Jul 7
CA $316
CA $736 total
Jul 6 - Jul 7
includes taxes & fees
9.8/10 Exceptional! (21 reviews)
"Great host"

Reviewed on May 23, 2026

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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

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 $1,074 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.

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.