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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $522, price is now $306 per person
$306
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $1,785, price is now $850 per person
$850
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $740, price is now $411 per person
$411
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
Price was $2,567, price is now $1,539 per person
$1,539
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
This condo resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free valet parking. Enjoy the gym and perks like free self parking and a free beach shuttle.
Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,767, price is now $1,092 per person
$1,092
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified 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.

Top Chokoloskee hotels deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
The Ultimate Fishing Retreat- Comfortable and Convenient!

The Ultimate Fishing Retreat- Comfortable and Convenient!

2 out of 5
$417 nightly
The price is $458 total per night
$458 total
Oct 5 - Oct 6
Total with taxes and fees
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

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

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Enjoy laundry facilities and air conditioning. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
Air conditioning
Laundry
Waterfront 2 bedroom 1 bath with boat slip

Waterfront 2 bedroom 1 bath with boat slip

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Enjoy free WiFi, laundry facilities, and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
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

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Enjoy a garden, laundry facilities, and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
Everglades Adventures Hotel Suites by Ivey House

Everglades Adventures Hotel Suites by Ivey House

2.5 out of 5
107 Camellia St E, Everglades City, FL
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $106 total per night
$106 total
Oct 7 - Oct 8
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
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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.

Smallwood Store

Frequently asked questions

How much are vacation packages to Chokoloskee?
$306 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

Photo by Noel Benadom
Photo by Noel Benadom
Photo by Noel Benadom
Photo by Noel Benadom