Chokoloskee Island Vacation Packages 2026 from $418

Chokoloskee Island flight + hotel vacation packages

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

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$418

per person

Apr 3 - Apr 6

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. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a picnic area, and luggage storage are also on offer.

Hyatt Vacation Club at Coconut Cove, Bonita Springs

$1,486

per person

Mar 19 - Mar 24

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.

Hilton Garden Inn Ft Myers

Villas

Save 100% on your flight

$444

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Hyatt Place Fort Myers/at The Forum

The Forum

Save 100% on your flight

$431

per person

Mar 16 - Mar 21

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.

Tween Waters Island Resort & Spa

Save 100% on your flight

$694

per person

Mar 1 - Mar 5

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.

Top Chokoloskee Island hotels deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL

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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

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

$165 nightly

$184 total

Jan 23 - Jan 24

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

Naples FL

$65 nightly

$73 total

Jan 19 - Jan 20

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

$81 nightly

$90 total

Jan 14 - Jan 15

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

Everglades City Motel

309 Collier Ave Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$117 total

Jan 14 - Jan 15

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, luggage storage, and laundry facilities are also on offer.

Parking included

Free WiFi

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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?

$418 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.