Chokoloskee Island Vacation Packages 2025 from $340

Chokoloskee Island flight + hotel vacation packages

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

Hilton Garden Inn Ft Myers

Villas

Save 100% on your flight

per person

Aug 24 - Aug 28

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) 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.

The Perry Hotel Naples

Save 100% on your flight

per person

Aug 27 - Sep 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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.

Bellasera Resort

Old Naples

Save 100% on your flight

per person

Aug 27 - Sep 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

This condo resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free valet parking. Enjoy the gym and perks like free self parking and a free beach shuttle.

GreenLinks Golf Villas at Lely Resort

Save 100% on your flight

per person

Aug 27 - Sep 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

A golf course, a full-service spa, and 2 outdoor tennis courts are all featured at this smoke-free aparthotel. Enjoy the outdoor pool and perks like free self parking. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.

Edison Beach House

Save 100% on your flight

per person

Aug 24 - Aug 28

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Fort Myers (RSW)

An outdoor pool, free self parking, and free newspapers are featured at this aparthotel. A terrace, a garden, and a picnic area are also on offer.

Top Chokoloskee Island hotels deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

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

Kitchen

Washer

The Ultimate Fishing Retreat- Comfortable and Convenient!

$417 nightly

$458 total

Jun 6 - Jun 7

Total includes taxes and fees

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

Kitchen

Washer

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

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Enjoy a garden, laundry facilities, and patios. Popular attractions Chokoloskee Bay and Gulf Coast Visitor Center are located nearby.

Kitchen

Washer

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

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Enjoy laundry facilities and air conditioning. Popular attractions Chokoloskee Bay and Gulf Coast Visitor Center are located nearby.

Air conditioning

Laundry

Waterfront 2 bedroom 1 bath with boat slip

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Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chokoloskee Bay and Gulf Coast Visitor Center are located nearby.

Kitchen

Free WiFi

Everglades Adventures Hotel Suites by Ivey House

107 Camellia St E, Everglades City, FL

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$121 total

Jun 9 - Jun 10

Total includes 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.

Pool

Parking included

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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?

$340 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.