Chokoloskee Holidays
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Top Flight + Hotel Deals in Chokoloskee
Price found within the past 48 hours. Click for updated prices.
Lani Kai Beachfront Resort
€659
per person
9 Oct - 13 Oct
found 22 hours ago
Return direct flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,947 reviews)
El hotel muy cómodo. Habitaciones limpias y camas cómodas. Acceso a la playa súper fácil. Personal súper amable y siempre dispuesto a ayudar. Comida excelente.
Reviewed on 1 Sept 2026
Casa Ybel Resort
Mid Island
€696
per person
9 Oct - 13 Oct
found 22 hours ago
Return direct flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (412 reviews)
The property is super convenient the beaches across the street a volleyball pool and then a huge lighted pool. The rooms were very clean older but clean and very comfortable. Mine felt like a little apartment tiki bar downstairs is great. The food is good. The drinks were good. They do play music until about midnight so if you don’t like music till that time, this isn’t the place for you lol. We will definitely stay here again.
Reviewed on 30 Aug 2026
Resort Harbour Properties
Punta Rassa
€703
per person
9 Oct - 13 Oct
found 7 hours ago
Return direct flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (372 reviews)
The property was clean and absolutely gorgeous. The pictures honestly didn't do it justice. The hospitality was great! The communication was top notch, but they weren't too much at all. Great privacy! Beach was steps away from the elevator. The location was wonderful! It was secluded but everything we needed was very close by. Sanibel Island was a 10 minute drive at most! We are only going to stay at this property in the future.
Reviewed on 11 Aug 2026
Top hotels in Chokoloskee
Deep Water Access with a Panoramic View of Chokoloskee Bay
Chokoloskee FL
9.8/10 Exceptional! (65 reviews)
"This is an amazing spot! Perfect for a fishing trip or if you just want to get away from it all and experience old Florida. The views and access to the water can’t be beat. The house was clean, comfortable and well stocked. Lynn is a great, communicative, friendly host who made it easy. I hope to ..."
Reviewed on 19 Jul 2026
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Chokoloskee FL
Waterfront 2 bedroom 1 bath with boat slip
Chokoloskee FL
10/10 Exceptional! (54 reviews)
"Place was spotless and nicely decorated. Great location for fishing. Great hospitality. Thanks for a great stay"
Reviewed on 24 May 2026
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.
What to do in Chokoloskee
Flamingo Marina: Backcountry Boat Tour of the Everglades
€41
per adult
Everglades National Park: Pontoon Boat Tour & Boardwalk
€52
per adult
100% of travellers recommend
Naples, FL: Manatee, Dolphin, 10,000 Islands Sunset Cruise
€112
per adult
Frequently asked questions
How much does a Chokoloskee holiday package cost?
Offering great value package deals from €659 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?
- 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.
- 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.
- 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.
- 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.
