Chokoloskee Vacations from $410

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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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $797, price is now $410 per person
$410
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,011 reviews)
The man that was working the night we checked in is very rude. We had two interactions with him and both were awful.

Reviewed on Oct 2, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,166, price is now $547 per person
$547
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (417 reviews)
Great all around 10/10 ; tigress restaurant is worth checking out as well

Reviewed on Sep 28, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $2,616, price is now $1,484 per person
$1,484
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
Our experience at La Playa was exceptional, everything was what we wanted and expected it to be

Reviewed on Sep 29, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $984, price is now $596 per person
$596
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,499 reviews)
Very clean rooms and the staff was great! Especially Ms Annie ….. she was wonderful!

Reviewed on Oct 1, 2025

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,059, price is now $656 per person
$656
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,219 reviews)
Joyful, relax and exceptional place in the center of the town. People at reception thanks to Tesse and her coworker was pleasant and welcoming , menu at Claw Bar and the London Club superbly delicious , service above and beyond accommodating , dream team of the cleaning crew (spotless clean, but invisible) , valet people friendly and entertaining . Whole experience during our stay was just perfect . Thank you , Bellasera , we will be back

Reviewed on Sep 29, 2025

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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 National Park Dolphin, Birding and Wildlife Boat Tour

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

$120
per adult
100% of travellers recommend
Everglades National Park Dolphin, Birding and Wildlife Boat Tour (2 hours)
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
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
9.8/10 Exceptional! (54 reviews)
"Property was in great location Property owner was friendly"

Reviewed on Jun 14, 2025

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Deep Water Access with a Panoramic View of Chokoloskee Bay
The Ultimate Fishing Retreat- Comfortable and Convenient!

The Ultimate Fishing Retreat- Comfortable and Convenient!

2 out of 5
Ochopee
$421 nightly
The price is $462 total per night from Oct 4 to Oct 5
$462 total
Oct 4 - Oct 5
Total with taxes and fees
9.6/10 Exceptional! (12 reviews)
"Great location! House is right next to boat ramp. House was as described. Would stay again"

Reviewed on Sep 1, 2025

The Ultimate Fishing Retreat- Comfortable and Convenient!
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
10/10 Exceptional! (4 reviews)
"Overall was great and as expected!"

Reviewed on Jul 22, 2025

Get rates
Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park
See all 243 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.

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 $410 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.

Explore a world of travel with Expedia

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.