Deals on vacations and trips to Chokoloskee

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Chokoloskee flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $633, price is now $419 per person
$419
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $1,274, price is now $700 per person
$700
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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.
Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,843, price is now $1,167 per person
$1,167
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and perks like a free beach shuttle. Enjoy the a rooftop terrace and unwind at the bar/lounge and poolside bar.
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,355, price is now $907 per person
$907
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,967, price is now $1,329 per person
$1,329
per person
Sep 15 - Sep 22
found 20 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) 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 hotels deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

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
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

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 Everglades basecamp with dock, trailer parking, and direct bay access

Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

Ochopee FL
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

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.
Kitchen
Washer
Waterfront 2 bedroom 1 bath with boat slip

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

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
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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?
$419 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.

Photos of local treasures

Browse Chokoloskee vacation photos for more inspiration

A calm lake with a clear sky and scattered clouds, surrounded by dense green forest.
A night sky with the Milky Way over a calm body of water and a rocky shoreline with wooden posts.
A wooden boardwalk leading through a forested area with a sunset sky.
A forested path surrounded by dense green foliage and trees.
A sunset over a body of water with two islands silhouetted against the sky.