Chokoloskee Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

Chokoloskee Holiday

Our pick of the best 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 5 Nov 2026

Get rates
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 9 Aug 2026

Get rates
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.

Stay near popular Chokoloskee attractions

Smallwood Store

Step back in time at this 1906 trading post that served as Chokoloskee Island's lifeline. Explore authentic artefacts while overlooking the same waters where Everglades pioneers once arrived by boat.
See properties

What to do in Chokoloskee

Flamingo Marina: Backcountry Boat Tour of the Everglades

Flamingo Marina: Backcountry Boat Tour of the Everglades

NZ$85
per adult
Flamingo Marina: Backcountry Boat Tour of the Everglades
Everglades National Park: Pontoon Boat Tour & Boardwalk

Everglades National Park: Pontoon Boat Tour & Boardwalk

NZ$108
per adult
100% of travellers recommend
Everglades National Park: Pontoon Boat Tour & Boardwalk
Everglades National Park: 2 hour Dolphin & Birding Boat Tour

Everglades: 2-hour Manatee, Dolphin & Birding Boat Tour

NZ$194
per adult
Everglades: 2-hour Manatee, Dolphin & Birding Boat Tour
See all activities in Chokoloskee

Frequently asked questions

How much does a Chokoloskee holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Chokoloskee costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chokoloskee?
The off-season is the best time to travel to Chokoloskee if you're trying to save. Another tip for scoring cheap Chokoloskee holiday packages? Avoid visiting during public holidays and any major events.
How many days is enough for Chokoloskee?
The ideal duration of your Chokoloskee holiday depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to visit all the main attractions and discover 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 holiday package well in advance.
Is it cheaper to book a Chokoloskee holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking flights and hotels separately. Better still, you can personalise 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 holiday 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. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Chokoloskee.
  2. Set your budget: Consider expenses like flights, meals and transportation when working out how much to save for your trip to Chokoloskee. Then, pick a hotel that suits your budget, whether that's an affordable stay or a swankier retreat.
  3. Decide how long to go away for: Now that you're more familiar with Chokoloskee, you can figure out the ideal length of your break. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Chokoloskee holiday package that brings all your bookings together.

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