Chokoloskee Island Vacation Packages

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Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
4.5-star property

The Perry Hotel Naples

9.6/10 Exceptional! (1,224 reviews)

Jan 23 - Jan 27

4 night stay

Boston (BOS) to Fort Myers (RSW)

Breeze Airways • Roundtrip • Coach
Price was $1,105, price is now $716 per person
$716
per person
found 1 day ago
Loved the stay while we were there, security was convenient so we felt safe. The only thing and it’s not really a negative thing it’s just the rooftop pool is right next to the rooftop restaurant. So while people are eating, they see you half naked swimming but other than that the stay was great. Will definitely come back and I encourage others to come here as well. Fabulous getaway for couples.

Reviewed on Nov 15, 2026

Southseas
3.0-star property

Southseas

No reviews

Feb 3 - Feb 10

7 night stay

Boston (BOS) to Fort Myers (RSW)

Breeze Airways • Roundtrip • Coach
Price was $3,951, price is now $2,550 per person
$2,550
per person
found 11 hours ago

Olde Marco Island Inn and Suites
3.0-star property

Olde Marco Island Inn and Suites

Olde Marco
8.8/10 Excellent! (1,003 reviews)

Feb 3 - Feb 10

7 night stay

Boston (BOS) to Fort Myers (RSW)

Breeze Airways • Roundtrip • Coach
Price was $2,253, price is now $1,529 per person
$1,529
per person
found 11 hours ago
The property is very nice with several on site restaurants and a decent bar and club for late nights. Its definitely for the older crowd but very enjoyable. The main bar and restaurant however is condemned and the whole property is going to be raised and replaced soon.

Reviewed on Nov 8, 2026

Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach
3.0-star property

Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach

South End
No reviews

Feb 3 - Feb 10

7 night stay

Boston (BOS) to Fort Myers (RSW)

Breeze Airways • Roundtrip • Coach
Price was $11,623, price is now $7,890 per person
$7,890
per person
found 11 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
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
0.22 mi from city center
Get rates
At Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park, guests have access to features like laundry facilities.
Air conditioning
Laundry
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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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