Deals on vacations and trips to Chokoloskee Island

Save when you book Chokoloskee Island package deals

Choose two or more items and save on your trip:

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 $726, price is now $395 per person
$395
per person
Nov 6 - Nov 12
found 1 day ago
Roundtrip 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 $1,926, price is now $909 per person
$909
per person
Dec 3 - Dec 8
found 1 day 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.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,123, price is now $543 per person
$543
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop 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.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $968, price is now $578 per person
$578
per person
Nov 9 - Nov 14
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.
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $851, price is now $514 per person
$514
per person
Nov 14 - Nov 18
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
This smoke-free hotel features 2 restaurants, 2 outdoor tennis courts, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

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

Get rates
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
Oct 1 - Oct 2
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

Get rates
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

Get rates
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
$108 nightly
The price is $120 total per night
$120 total
Oct 12 - Oct 13
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
Port of the Islands Everglades Adventure Resort

Port of the Islands Everglades Adventure Resort

2.5 out of 5
$61 nightly
The price is $68 total per night
$68 total
Oct 5 - Oct 6
Total with taxes and fees
A marina and an outdoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Parking included
Don't see what you're looking for?
See all available properties in Chokoloskee Island
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 Island?
$395 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

Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity