Name: The Ultimate Fishing Retreat- Comfortable and Convenient!
Price range: $537 total

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The Latest Chokoloskee Island vacation packages

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

The Perry Hotel Naples

Save 100% on your flight

$671

per person

Jun 27 - Jul 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (788 reviews)

The pools are fantastic. Rooms are spacious. Bar staff a bit lacking. Parking a bit awkward.

Reviewed on May 11, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,047

per person

Jun 27 - Jul 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,005 reviews)

Great resort. Beautiful beach. Great restaurant. Close to 5th Ave South

Reviewed on May 9, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$908

per person

Jul 18 - Jul 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (857 reviews)

Very relaxing beautiful property in a beautiful surroundings setting. Five star responsive staff. Great location with shops, dining and entertainment from onsite all the way to Ft Myers north and Naples south.

Reviewed on May 11, 2026

Tween Waters Island Resort & Spa

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$1,289

per person

Jul 3 - Jul 10

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,001 reviews)

The property was quieter than expected which was nice.

Reviewed on May 12, 2026

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$858

per person

Jul 18 - Jul 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

10/10 Exceptional! (1 review)

Very clean, modern and fun room design, my daughter loved the bunk beds! The pool and other amenities like the barbeques were great! Staff were super friendly and the hotel was right on the beach. Close to Fort Myers for entertainment but in a more peaceful, exclusive spot with a nicer beach, perfect for families.

Reviewed on May 13, 2026

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Chokoloskee Island Hotel Deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL

9.8/10 Exceptional! (63 reviews)

Had a great time in Chokoloskee, exploring the area by boat. We had our own small boat, and we launched it and kept it at the dock while staying at this beautiful home on the water. We had some great fishing, even though unfamiliar with that part of the water in Florida. It does get shallow, so smaller ...

Reviewed on Mar 31, 2026

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Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Chokoloskee FL

9.6/10 Exceptional! (134 reviews)

We enjoyed our stay. It was great for our fishing retreat.

Reviewed on Apr 28, 2026

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The Ultimate Fishing Retreat- Comfortable and Convenient!

Ochopee FL

$490 nightly

$537 total

May 22 - May 23

Total with taxes and fees

See all 204 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.