Chokoloskee Vacation Packages 2026 from $594

Chokoloskee flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Casa Tiki

Hancock

Save 100% on your flight

$594

per person

Sep 13 - Sep 20

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

This vacation home features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. Luggage storage, laundry facilities, and barbecue grills are also on offer.

A Wave From it All

Siesta Isle

Save 100% on your flight

$1,722

per person

Sep 6 - Sep 13

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

This vacation home features 6 beach bars and an outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, barbecue grills, and a virtual front desk are also on offer.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,141

per person

Oct 15 - Oct 19

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

GullWing Beach Resort

South Island

Save 100% on your flight

$1,015

per person

Oct 10 - Oct 17

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This aparthotel features an outdoor pool and a gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, laundry facilities, and concierge services are also on offer.

Tween Waters Island Resort & Spa

Save 100% on your flight

$1,479

per person

Oct 10 - Oct 17

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free resort features a private beach, a full-service spa, and a marina. Family-friendly amenities include a children's pool and kid-friendly dining, along with kayaking. Free self parking is free for guests, and you can enjoy a meal in one of the 3 restaurants.

Top Chokoloskee hotels deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL

Get rates

This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

Chokoloskee FL

Get rates

An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

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

Ochopee FL

Get rates

This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL

Get rates

Enjoy free WiFi, laundry facilities, and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.

Kitchen

Free WiFi

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

Chokoloskee FL

Get rates

Enjoy a garden, laundry facilities, and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.

Kitchen

Washer

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

Chokoloskee FL

Get rates

Enjoy laundry facilities and air conditioning. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.

Don't see what you're looking for?

See all available properties in Chokoloskee

View all properties

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

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

Frequently asked questions

How much are vacation packages to Chokoloskee?

$594 is all you need to spend for a memorable escape in Chokoloskee. Bundle your flights and hotel into a Travelocity package and watch how the savings add up. With prices as good as these, there's never been a better time to travel.

How long should my Chokoloskee vacation be?

Most travelers reserve their hotel for 2 nights in Chokoloskee. But that doesn't necessarily mean you have to do the same. How long you decide to stay depends on what you plan to do during your vacation. If your aim is to familiarize yourself with every nook and cranny of this impressive destination, stay another couple of nights (or even longer!).

Where can I get the best vacation package deals for Chokoloskee?

You'll come across an amazing range of Chokoloskee package deals on Travelocity. With as many as 400 airlines and 1,000,000 worldwide properties, piecing together your ideal getaway won't take long.

Why should I book my Chokoloskee vacation package via Travelocity?

Travel is all about making fantastic new memories and leaving all your troubles behind — which is why we provide you with a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our impressive range of package deals. So what are you waiting for? There's no time like the present to secure the vacation of a lifetime.

Can I save money on my Chokoloskee car rental if I book it with my hotel or flight?

You most certainly can — combine your hotel, flight and car into a Chokoloskee vacation package and you can save a handsome sum. With so much to see in and around Chokoloskee, that set of wheels will make exploring a breeze. Once you've slid into the driver's seat, crank up the tunes and head toward Vizcaya Museum and Gardens, a top attraction approximately 70 mi from Chokoloskee.

Which airport is best for Chokoloskee?

One top option is Southwest Florida Intl. Airport (RSW). From here, you'll need to travel southeast for about 55 mi to reach inner Chokoloskee. Another choice is Naples Municipal Airport (APF), 35 mi away from central Chokoloskee.

Where should I stay when visiting Chokoloskee?

Many visitors check in to the Outdoor Resorts of Chokoloskee. It's the perfect base for your Chokoloskee vacation.