Chokoloskee Vacation Packages 2026 from $719

Chokoloskee 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

$719

per person

Nov 11 - Nov 15

found 2 days ago

Roundtrip non-stop 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.

Tween Waters Island Resort & Spa

Save 100% on your flight

$757

per person

Nov 11 - Nov 15

found 2 days ago

Roundtrip non-stop 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.

The Perry Hotel Naples

Save 100% on your flight

$985

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip non-stop 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.

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$936

per person

Dec 18 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$931

per person

Dec 18 - Dec 23

107 Camellia St E Everglades City FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$103 total

Oct 4 - Oct 5

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

$70 nightly

$77 total

Oct 4 - Oct 5

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 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?

$719 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.