Chokoloskee Island Vacation Packages 2026 from $717

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The Latest Chokoloskee Island vacation packages

Price found within the past 48 hours. Click for updated prices.

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$717

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (87 reviews)

The Perry Hotel Naples

Save 100% on your flight

$971

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

Un croissant con un café $18 dólares. No hay opciones para un buen desayuno, lo mismo con la comida.

Reviewed on Aug 16, 2026

Manasota Key Resort

Save 100% on your flight

$1,387

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (307 reviews)

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

Save 100% on your flight

$749

per person

Nov 8 - Nov 14

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

9.8/10 Exceptional! (1,283 reviews)

Love that this is a two bedroom suite with kitchen and living space. You’re close to shopping restaurants and you can watch the sunset at the tiki bar right outside your rooms.

Reviewed on Aug 15, 2026

Casa Ybel Resort

Mid Island

Save 100% on your flight

$939

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (397 reviews)

Loved the location & the beach The only negative is that you need to pay a lot of money for the beach chairs Beautiful sunsets

Reviewed on Aug 14, 2026

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Stay near popular Chokoloskee Island attractions

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.

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Chokoloskee Island Hotel Deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL

9.8/10 Exceptional! (65 reviews)

"This is an amazing spot! Perfect for a fishing trip or if you just want to get away from it all and experience old Florida. The views and access to the water can’t be beat. The house was clean, comfortable and well stocked. Lynn is a great, communicative, friendly host who made it easy. I hope to ..."

Reviewed on Jul 19, 2026

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

Chokoloskee FL

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Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL

10/10 Exceptional! (54 reviews)

"Place was spotless and nicely decorated. Great location for fishing. Great hospitality. Thanks for a great stay"

Reviewed on May 24, 2026

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See all 199 properties in Chokoloskee Island

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.