Deals on vacations and trips to Chokoloskee

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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 $934, price is now $573 per person
$573
per person
Dec 5 - Dec 9
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.
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,364, price is now $856 per person
$856
per person
Jan 3 - Jan 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
This hotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. Laundry facilities are provided for your convenience.
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Price was $1,954, price is now $1,344 per person
$1,344
per person
Jan 11 - Jan 18
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
This smoke-free condo features a private beach, a full-service spa, and 2 restaurants. Enjoy the 5 outdoor tennis courts and perks like free self parking and free WiFi. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was $978, price is now $685 per person
$685
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
An outdoor pool is featured at this apartment, along with free WiFi in public areas and a virtual front desk.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $962, price is now $678 per person
$678
per person
Jan 1 - Jan 6
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

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

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

Chokoloskee FL
Get rates
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 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
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 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
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

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

Ochopee FL
$424 nightly
The price is $465 total per night
$465 total
Oct 25 - Oct 26
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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
$109 nightly
The price is $121 total per night
$121 total
Oct 25 - Oct 26
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.

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?
$573 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.