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.
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 $708, price is now $508 per person
$508
per person
Apr 13 - Apr 16
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.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,399, price is now $892 per person
$892
per person
Apr 22 - Apr 27
found 2 days ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a picnic area, and luggage storage are also on offer.
Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,128, price is now $745 per person
$745
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,334, price is now $908 per person
$908
per person
Apr 22 - Apr 27
found 2 days ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free condo resort. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. A coffee shop, a snack bar/deli, and a picnic area are also on offer.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,030, price is now $711 per person
$711
per person
May 21 - May 24
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.

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 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
The Ultimate Fishing Retreat- Comfortable and Convenient!

The Ultimate Fishing Retreat- Comfortable and Convenient!

2 out of 5
Ochopee 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?
$508 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 Bay in the Ten Thousand Islands of southwest Florida USA
The amazingly dark skies of Chokoloskee Island, FL provide great views of the night sky. While there, check out some of the boat tours and fishing charters. #beachtips #florida #chokoloskee #island #milkyway #astronomy #beach #ocean #BVSblue
Everglades National Park which includes a bridge, forests and a sunset
Everglades National Park showing forest scenes