Chokoloskee Vacation Packages 2026 from $508

Chokoloskee flight + hotel vacation packages

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

Courtyard by Marriott Fort Myers Cape Coral

Save 100% on your flight

$508

per person

Feb 17 - Feb 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Hilton Garden Inn Ft Myers

Villas

$549

per person

Feb 17 - Feb 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Hyatt Place Fort Myers/at The Forum

The Forum

Save 100% on your flight

$679

per person

Feb 17 - Feb 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

The Perry Hotel Naples

Save 100% on your flight

$910

per person

Mar 26 - Mar 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a beach shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy the a rooftop terrace.

Home2 Suites by Hilton Fort Myers Colonial Blvd

Save 100% on your flight

$716

per person

Feb 17 - Feb 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

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

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.

Air conditioning

Laundry

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

Chokoloskee 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

Location, Hidden Gem, Fishing, Paradise, Sunsets, Relax on the Bay 1274 sq ft

Chokoloskee FL

Get rates

This condo features an outdoor pool and a gym. A garden, laundry facilities, and barbecue grills are also on offer.

Pool

Kitchen

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

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.

Popular places to visit

Smallwood Store

You can spend time exploring the galleries in Smallwood Store during your trip to Chokoloskee. You can seek out the fishing spots while in the area.

Frequently asked questions

How much are vacation packages to Chokoloskee?

$508 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.