Chokoloskee Island Vacation Packages 2026 from $407

Chokoloskee Island flight + hotel vacation packages

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

Hyatt Place Fort Myers/at The Forum

The Forum

Save 100% on your flight

$407

per person

Feb 24 - Mar 1

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Hilton Garden Inn Ft Myers

Villas

Save 100% on your flight

$473

per person

Feb 24 - Mar 1

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$466

per person

Feb 22 - Feb 25

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a picnic area, and luggage storage are also on offer.

Tween Waters Island Resort & Spa

Save 100% on your flight

$795

per person

Mar 9 - Mar 14

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Courtyard by Marriott Fort Myers Cape Coral

Save 100% on your flight

$452

per person

Feb 24 - Mar 1

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Top Chokoloskee Island hotels deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL

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

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

Chokoloskee FL

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

Port of the Islands Everglades Adventure Resort

Naples FL

$107 nightly

$119 total

Jan 26 - Jan 27

Total with taxes and fees

A marina and an outdoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Everglades Adventures Hotel Suites by Ivey House

107 Camellia St E Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$170 nightly

$189 total

Jan 25 - Jan 26

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Luggage storage is also provided.

Captain's Table Hotel

202 Broadway Ave E Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$128 total

Jan 27 - Jan 28

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. A computer station and luggage storage are also provided.

Everglades City Motel

309 Collier Ave Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$117 total

Jan 25 - Jan 26

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, luggage storage, and laundry facilities are also on offer.

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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 Island?

$407 is all you need to spend for a memorable vacation in Chokoloskee Island. Bundle your flights and hotel into a vacation package with Travelocity and see how much the savings start to grow. With prices as good as these, it's never been easier to travel!

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

You'll discover a tempting selection of Chokoloskee Island package deals on Travelocity. With 400 partner airlines and 1,000,000 properties worldwide, crafting your ideal vacation will be simple.

Why should I purchase my Chokoloskee Island vacation package via Travelocity?

From our 24/7 support to our range of incredible destinations, we're committed to fulfilling your travel dreams. All you'll have to do is to click and book — our Price Match Guarantee will make sure you score the best price.

Will I save money on my Chokoloskee Island car rental if I combine it with hotels and flights?

Bundling your bookings into a Chokoloskee Island vacation package will leave you with a nice chunk of spare change. You can combine a car and flight; a hotel, flight and car; or a car and hotel. There's no better way to discover the greater Chokoloskee Island area than from the comfort of your own rental car. You can also add activities and experiences to your Travelocity package.

Which airport is best for Chokoloskee Island?

Choose from Southwest Florida Intl. Airport (RSW) or Naples Municipal Airport (APF). They are the major airports for people flying in and out of Chokoloskee Island.