Deals on vacations and trips to Chokoloskee

Save when you book Chokoloskee package deals

Choose two or more items and save on your trip:

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 $571, price is now $386 per person
$386
per person
Aug 26 - Aug 29
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.
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 $1,626, price is now $981 per person
$981
per person
Jul 6 - Jul 11
found 1 day 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.
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4 out of 5
Price was $805, price is now $525 per person
$525
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
This smoke-free condo features a marina and 7 restaurants. Dine at the beachfront restaurant and relax with beach umbrellas. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas.
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,082, price is now $750 per person
$750
per person
Aug 19 - Aug 23
found 1 day 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.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $772, price is now $547 per person
$547
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. Relax with a drink at one of the 2 poolside bars and enjoy the 2 hot tubs and 24-hour gym.

Top Chokoloskee hotels deals

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
Get rates
Enjoy a garden, laundry facilities, and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
Kitchen
Washer
Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Waterfront 2 bedroom 1 bath with boat slip

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL
Get rates
Enjoy free WiFi, laundry facilities, and patios. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
Kitchen
Free WiFi
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

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

Ochopee FL
$477 nightly
The price is $524 total per night
$524 total
Jun 10 - Jun 11
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

Chokoloskee FL
Get rates
Enjoy laundry facilities and air conditioning. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.
Air conditioning
Laundry
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise

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

Chokoloskee FL
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Chokoloskee
View all properties
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?
$386 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

Chokoloskee Bay in the Ten Thousand Islands of southwest Florida USA
Chokoloskee
Chokoloskee
Chokoloskee
Chokoloskee