Chokoloskee Island Vacation Packages 2026 from $785

Chokoloskee Island flight + hotel vacation packages

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

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$785

per person

Jan 14 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this hotel. Relax with a drink at one of the 2 poolside bars and get perks like free WiFi. Relax with a drink at one of the 9 bars/lounges and enjoy the 24-hour gym.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$3,290

per person

Jan 9 - Jan 16

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.

Latitude 26 Waterfront Resort & Marina

Save 100% on your flight

$1,028

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

A marina and an outdoor pool are featured at this smoke-free motel. Enjoy a meal from the restaurant and perks like free continental breakfast and free self parking. Free WiFi in public areas, a picnic area, and express check-in are also on offer.

Tween Waters Island Resort & Spa

$961

per person

Dec 9 - Dec 16

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.

Windward Passage Resort

$815

per person

Dec 9 - Dec 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. Laundry facilities are provided for your convenience.

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

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

Chokoloskee FL

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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

$109 nightly

$121 total

Dec 1 - Dec 2

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

$91 nightly

$101 total

Dec 1 - Dec 2

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?

$785 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.