Chokoloskee Vacations from $531

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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.

The Latest Chokoloskee vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Save 100% on your flight
Price was $917, price is now $531 per person
$531
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,004 reviews)
Great hotel Great people and service. Very good breakfast

Reviewed on Jan 2, 2026

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $1,004, price is now $540 per person
$540
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
The staff at the counter are not friendly at all, the room was just clean.

Reviewed on Jan 6, 2026

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $2,024, price is now $1,142 per person
$1,142
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
A great place to stay. Very clean. Very professionally run. Great breakfast options included. Incredible work out facility. I’d highly recommend Innovation

Reviewed on Jan 3, 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $906, price is now $538 per person
$538
per person
Mar 17 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Erica was wonderful, she was very pleasant and very accommodating.

Reviewed on Jan 2, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,440, price is now $870 per person
$870
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
Nice rooms and amenities, clean. Need to improve food quality in all restaurants and the smell of food that is all over.

Reviewed on Jan 8, 2026

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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

$110
per adult
Everglades: 2 hour Manatee, Dolphin & Birding Boat Tour
Everglades: Mangrove, Grassland Airboat Tours, & Boardwalk

Everglades: Mangrove, Grassland Airboat Tours, & Boardwalk

$140
per adult
80% of travellers recommend
Everglades: Mangrove, Grassland Airboat Tours, & Boardwalk
Small Group Motorboat Eco Tour of the Everglades

Small Group Motorboat Eco Tour of the Everglades

$149
per adult
Small Group Motorboat Eco Tour of the Everglades
See all activities in Chokoloskee

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
9.8/10 Exceptional! (58 reviews)
We used this as a jump off point to kayak the waterway, wonderful position and stay

Reviewed on Dec 3, 2025

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Deep Water Access with a Panoramic View of Chokoloskee Bay
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
9.4/10 Exceptional! (6 reviews)
National park was very close fishin was amazing place was extremely clean and cozy I loved every second

Reviewed on Nov 20, 2025

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

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL
10/10 Exceptional! (47 reviews)
Heather was very helpful when we arrived and helped get us acquainted with the docking at the house which was very nice. The tiny house was immaculately clean and very nicely decorated. I would highly recommend this to anyone wanting a nice little fishing cabin with a dock and access to the ...

Reviewed on Dec 6, 2025

Get rates
Waterfront 2 bedroom 1 bath with boat slip
See all 260 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.

Find the Best Chokoloskee Vacation Packages

Chokoloskee Essential Information

Language
English
Currency
U.S dollars
Population
360
Top Sights
Museum of the Everglades and Everglades City Hall

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Frequently asked questions

How much does a Chokoloskee vacation package cost?
Offering great value package deals from $531 on Expedia, you'll be thrilled with how little a vacation to Chokoloskee costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chokoloskee?
September, October and December are great times to look for cheap Chokoloskee vacation packages. Traveling in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Chokoloskee?
The ideal length of your Chokoloskee vacation depends on what you'd like to see and do. Usually, a few days to a week will give you plenty of time to go to all the top sights and explore some hidden spots along the way.
How to find the best Chokoloskee package deals?
Use Expedia's filter tool to find some unbeatable Chokoloskee package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Chokoloskee package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Chokoloskee vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels separately. Better still, you can personalize your Chokoloskee trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chokoloskee?
If you're considering a spontaneous Chokoloskee adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Chokoloskee?

  1. Choose your travel dates: The things you'd like to do in Chokoloskee and your preferred season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and meals to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Chokoloskee.
  3. Explore Chokoloskee using Expedia's trip planning tool: Gain insights into the most popular attractions and best properties for your trip to Chokoloskee. You can also save your favorite locations, collaborate with your group and manage all your plans in one place.
  4. Decide your trip length: Consider how long you'd like to spend discovering Chokoloskee. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  5. Combine your accommodations and airfare: Once you've settled on your dates and duration, book the right Chokoloskee vacation package for you.
  6. Book experiences or activities in advance: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Chokoloskee. Find all the incredible things to do in Chokoloskee with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Chokoloskee vacation packages?
If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Chokoloskee vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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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.