Chokoloskee Island Vacation Packages 2026 from $677

Chokoloskee Island flight + hotel vacation packages

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

Casa Tiki

Hancock

Save 100% on your flight

$677

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Tween Waters Island Resort & Spa

Save 100% on your flight

$1,018

per person

Oct 14 - Oct 21

found 1 day 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.

South Seas

Save 100% on your flight

$984

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free resort features a private beach, a golf course, and a water park. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. You'll find 5 restaurants and 6 outdoor pools on site, along with a bar/lounge to unwind.

Manasota Key Resort

Save 100% on your flight

$927

per person

Sep 14 - Sep 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free hotel's private beach and marina are among the highlights. Enjoy the outdoor pool and perks like free self parking and free WiFi. A terrace, a picnic area, and laundry facilities are also on offer.

The Perry Hotel Naples

Save 100% on your flight

$834

per person

Oct 23 - Oct 26

107 Camellia St E Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$110 total

Aug 19 - Aug 20

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

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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.

Stay near popular Chokoloskee Island attractions

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.

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Frequently asked questions

How much are vacation packages to Chokoloskee Island?

$677 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.