Chokoloskee Island Vacation Packages 2025/2026 from $297

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

$297

per person

Dec 18 - Dec 22

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.

Innovation Hotel

$954

per person

Jan 12 - Jan 17

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Fort Myers (RSW)

This smoke-free hotel features 2 restaurants, 2 outdoor tennis courts, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

The Perry Hotel Naples

Save 100% on your flight

$387

per person

Dec 8 - Dec 12

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.

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$370

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

3 outdoor pools, a lazy river, and a gym are all featured at this smoke-free aparthotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

Landing Apartments - Cape Coral

Caloosahatchee

Save 100% on your flight

$527

per person

Dec 5 - Dec 12

just found

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

This aparthotel features an outdoor pool and a gym. Enjoy the a rooftop terrace and perks like free self parking and free WiFi. Barbecue grills and a virtual front desk are also provided.

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!

$421 nightly

$462 total

Nov 6 - Nov 7

Total with taxes and fees

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

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

Air conditioning

Laundry

Everglades Adventures Hotel Suites by Ivey House

107 Camellia St E, Everglades City, FL

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$143 total

Nov 16 - Nov 17

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.

Pool

Parking included

Port of the Islands Everglades Adventure Resort

$145 nightly

$162 total

Nov 6 - Nov 7

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.

Pool

Parking included

Captain's Table Hotel

202 Broadway Ave E, Everglades City, FL

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$86 total

Dec 5 - Dec 6

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.

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?

$297 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.