Chokoloskee Vacation Packages 2026 from $642

Chokoloskee flight + hotel vacation packages

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

The Perry Hotel Naples

Save 100% on your flight

$642

per person

Dec 5 - Dec 8

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.

Landing Apartments Fort Myers near Eastwood Village

Save 100% on your flight

$1,154

per person

Dec 23 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

An outdoor pool is featured at this apartment, along with free WiFi in public areas and a virtual front desk.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$4,161

per person

Dec 23 - Dec 30

found 16 hours 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.

Casa Ybel Resort

Mid Island

Save 100% on your flight

$657

per person

Nov 14 - Nov 18

found 12 hours 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 Immokalee Road - Naples

Rural Estates

Save 100% on your flight

$827

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

This apartment's 2 outdoor pools and gym are among the featured amenities. Business travelers can take advantage of the free WiFi in public areas. Free self parking, barbecue grills, and a virtual front desk are also on offer.

Top Chokoloskee hotels deals

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.

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.

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.

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.

Everglades Adventures Hotel Suites by Ivey House

107 Camellia St E Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$103 total

Oct 5 - Oct 6

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.

Captain's Table Hotel

202 Broadway Ave E Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$77 total

Oct 5 - Oct 6

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.

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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 attractions

Chokoloskee Bay

9.2/10 (148 reviews)

Commune with nature and explore the great outdoors at Chokoloskee Bay during your travels in Chokoloskee. Stroll along the marina in this relaxing area, or seek out the kayaking spots.

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Frequently asked questions

How much are vacation packages to Chokoloskee?

$642 is all you need to spend for a memorable escape in Chokoloskee. Bundle your flights and hotel into a Travelocity package and watch how the savings add up. With prices as good as these, there's never been a better time to travel.

How long should my Chokoloskee vacation be?

Most travelers reserve their hotel for 2 nights in Chokoloskee. But that doesn't necessarily mean you have to do the same. How long you decide to stay depends on what you plan to do during your vacation. If your aim is to familiarize yourself with every nook and cranny of this impressive destination, stay another couple of nights (or even longer!).

Where can I get the best vacation package deals for Chokoloskee?

You'll come across an amazing range of Chokoloskee package deals on Travelocity. With as many as 400 airlines and 1,000,000 worldwide properties, piecing together your ideal getaway won't take long.

Why should I book my Chokoloskee vacation package via Travelocity?

Travel is all about making fantastic new memories and leaving all your troubles behind — which is why we provide you with a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our impressive range of package deals. So what are you waiting for? There's no time like the present to secure the vacation of a lifetime.

Can I save money on my Chokoloskee car rental if I book it with my hotel or flight?

You most certainly can — combine your hotel, flight and car into a Chokoloskee vacation package and you can save a handsome sum. With so much to see in and around Chokoloskee, that set of wheels will make exploring a breeze. Once you've slid into the driver's seat, crank up the tunes and head toward Vizcaya Museum and Gardens, a top attraction approximately 70 mi from Chokoloskee.

Which airport is best for Chokoloskee?

One top option is Southwest Florida Intl. Airport (RSW). From here, you'll need to travel southeast for about 55 mi to reach inner Chokoloskee. Another choice is Naples Municipal Airport (APF), 35 mi away from central Chokoloskee.

Where should I stay when visiting Chokoloskee?

Many visitors check in to the Outdoor Resorts of Chokoloskee. It's the perfect base for your Chokoloskee vacation.