Chokoloskee Island Vacation Packages 2026 from $386

Chokoloskee Island flight + hotel vacation packages

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

Quality Inn Fort Myers Cape Coral

$386

per person

Jan 14 - Jan 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the laundry service. There's an outdoor pool on site, and a 24-hour front desk and a garden are also provided.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

$1,668

per person

Jan 14 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

Tween Waters Island Resort & Spa

$557

per person

Jan 14 - Jan 17

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.

Manasota Key Resort

$1,352

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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.

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Save 100% on your flight

$2,108

per person

Jan 14 - Jan 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A terrace is also provided.

Top Chokoloskee Island hotels deals

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

Chokoloskee FL

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An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Pool

Kitchen

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL

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Enjoy free WiFi, laundry facilities, and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.

Kitchen

Free WiFi

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

Chokoloskee FL

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Enjoy a garden, laundry facilities, and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.

Kitchen

Washer

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

Oct 28 - Oct 29

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

Captain's Table Hotel

202 Broadway Ave E Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$91 total

Oct 29 - Oct 30

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

Extreme Naples Charters- "Comfort Zone"-Social Distancing at it's Best!

Naples FL

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An outdoor pool is featured at this houseboat, along with a garden and concierge services. Barbecue grills are provided for your convenience.

Pool

Kitchen

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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?

$386 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.