Chokoloskee Island Vacation Packages 2026 from $626

Chokoloskee Island flight + hotel vacation packages

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

Casa Ybel Resort

Mid Island

Save 100% on your flight

$626

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features 2 restaurants, 6 outdoor tennis courts, and an outdoor pool. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$1,150

per person

Dec 2 - Dec 9

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This apartment features an outdoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference center. There's a rooftop terrace on site, and concierge services and barbecue grills are also offered.

The Perry Hotel Naples

Save 100% on your flight

$880

per person

Nov 12 - Nov 15

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.

GreenLinks Golf Villas at Lely Resort

Save 100% on your flight

$798

per person

Dec 2 - Dec 9

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free aparthotel features a golf course, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking. You'll appreciate the gym, bar/lounge, and barbecue grills.

Park Shore Resort

Park Shore

Save 100% on your flight

$933

per person

Dec 2 - Dec 9

107 Camellia St E Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$84 total

Sep 11 - Sep 12

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

$60 nightly

$66 total

Sep 11 - Sep 12

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.

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?

$626 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.