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
Save 100% on your flight
Price was $713, price is now $468 per person
$468
per person
Jun 1 - Jun 5
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
Save 100% on your flight
Price was $1,649, price is now $847 per person
$847
per person
Jun 4 - Jun 8
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.
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Save 100% on your flight
Price was $1,047, price is now $693 per person
$693
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop 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.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $916, price is now $615 per person
$615
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
3 outdoor pools, a lazy river, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was $1,377, price is now $977 per person
$977
per person
Jun 21 - Jun 27
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this smoke-free resort. Enjoy the 5 outdoor tennis courts and indoor pool, and unwind with a drink at the bar/lounge.

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
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
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
The Ultimate Fishing Retreat- Comfortable and Convenient!

The Ultimate Fishing Retreat- Comfortable and Convenient!

Ochopee FL
$447 nightly
The price is $491 total per night
$491 total
Apr 22 - Apr 23
Total with taxes and fees
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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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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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?
$468 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
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