Chokoloskee Island Vacation Packages

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Top Chokoloskee Island vacation package deals

Price found within the past 48 hours. Click for updated prices.
Marco Beach Ocean Suites
2.0-star property

Marco Beach Ocean Suites

South End
8.8/10 Excellent! (1,548 reviews)

Dec 14 - Dec 17

3 night stay

Nashville (BNA) to Fort Myers (RSW)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $931, price is now $596 per person
$596
per person
found 1 day ago
Great hotel, right on the beach. Very convenient and well maintained. Nice short walk to restaurants. A super place to stay.

Reviewed on Oct 13, 2026

The Perry Hotel Naples
4.5-star property

The Perry Hotel Naples

9.6/10 Exceptional! (1,182 reviews)

Dec 10 - Dec 14

4 night stay

Boston (BOS) to Fort Myers (RSW)

Allegiant Air • Coach

Fort Myers (RSW) to Boston (BOS)

Delta • Coach
Save 100% on your flight
Price was $1,627, price is now $990 per person
$990
per person
found 1 day ago

Southseas
3.0-star property

Southseas

No reviews

Dec 26 - Jan 2

7 night stay

Indianapolis (IND) to Fort Myers (RSW)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,156, price is now $2,958 per person
$2,958
per person
found 1 day ago

Landing Furnished Apartments minutes from Downtown Fort Myers
3.0-star property

Landing Furnished Apartments minutes from Downtown Fort Myers

Hancock
10/10 Exceptional! (1 review)

Dec 22 - Dec 28

6 night stay

Boston (BOS) to Fort Myers (RSW)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,603, price is now $1,144 per person
$1,144
per person
found 1 day ago
Clean, quiet, perfect alternative to a hotel

Reviewed on Oct 7, 2026

Lighthouse Resort and Club
4.0-star property

Lighthouse Resort and Club

East End
No reviews

Nov 28 - Dec 5

7 night stay

Boston (BOS) to Fort Myers (RSW)

Delta • Coach

Fort Myers (RSW) to Boston (BOS)

Breeze Airways • Coach
Save 100% on your flight
Price was $1,715, price is now $1,234 per person
$1,234
per person
found 7 hours ago

Top rated hotels for your Chokoloskee Island vacation package

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

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

Chokoloskee FL
0.14 mi from city center
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At this vacation home, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free vacation home also has barbecue grills.
Pool
Kitchen
Waterfront 2 bedroom 1 bath with boat slip

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL
0.25 mi from city center
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At Waterfront 2 bedroom 1 bath with boat slip, guests have access to features like laundry facilities.
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
0.15 mi from city center
Get rates
At Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands, guests have access to features like laundry facilities.
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.
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