Deals on vacations and trips to Chokoloskee Island

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Chokoloskee Island 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 $637, price is now $303 per person
$303
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,660, price is now $746 per person
$746
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip non-stop 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.
Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was $1,888, price is now $918 per person
$918
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,153, price is now $646 per person
$646
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
An outdoor pool, free self parking, and free newspapers are featured at this aparthotel. A terrace, a garden, and a picnic area are also on offer.
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
Price was $754, price is now $471 per person
$471
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the gym and free cooked-to-order breakfast each morning.

Top Chokoloskee Island 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
Sep 9 - Sep 10
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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.
Kitchen
Washer
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.
Kitchen
Free WiFi
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
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
$96 nightly
The price is $107 total per night
$107 total
Sep 9 - Sep 10
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 Island?
$303 is all you need to spend for a memorable vacation in Chokoloskee Island. Bundle your flights and hotel into a vacation package with Travelocity and see how much the savings start to grow. With prices as good as these, it's never been easier to travel!
Where can I get the best vacation package deals for Chokoloskee Island?
You'll discover a tempting selection of Chokoloskee Island package deals on Travelocity. With 400 partner airlines and 1,000,000 properties worldwide, crafting your ideal vacation will be simple.
Why should I purchase my Chokoloskee Island vacation package via Travelocity?
From our 24/7 support to our range of incredible destinations, we're committed to fulfilling your travel dreams. All you'll have to do is to click and book — our Price Match Guarantee will make sure you score the best price.
Will I save money on my Chokoloskee Island car rental if I combine it with hotels and flights?
Bundling your bookings into a Chokoloskee Island vacation package will leave you with a nice chunk of spare change. You can combine a car and flight; a hotel, flight and car; or a car and hotel. There's no better way to discover the greater Chokoloskee Island area than from the comfort of your own rental car. You can also add activities and experiences to your Travelocity package.
Which airport is best for Chokoloskee Island?
Choose from Southwest Florida Intl. Airport (RSW) or Naples Municipal Airport (APF). They are the major airports for people flying in and out of Chokoloskee Island.

Photos of local treasures

Browse Chokoloskee Island vacation photos for more inspiration

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