
Chokoloskee Island Vacations from $592
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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
Price was $901, price is now $592 per person
$592
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (75 reviews)
We enjoyed our stay very much. Checkin outside and at front desk was fast. We felt bad for the attendants outside as we were staying in the villas and we had a few heavy items. We felt it could have been an easier checkin ( shorter distance) for everyone at the valet entrance farther down closer to where sunsuites were. We had forgotten about this area. All our family used valet for their vehicles at that entrance.
We had the 3-bedroom villa which was spotless clean and so nicely decorated. The appliances were top notch ( it took a little time to learn how to operate everything). One suggestion might be a lil card with simple instructions on operation of ice maker, oven, and dishwasher. Also WiFi instructions somewhere would have saved us asking the bell hop about an access number which we didn't need.
The beds were so comfortable as well as bedding and pillows. All window coverings worked beautifully. We had a magnificent view of the peace harbor and loved the massive deck on both sides.
We had 5 people staying and 2 dogs. We did have to circulate the dinnerware as there are only 4 of everything except coffee cups & glasses. Please add a silicone flexible turner for cooking. If we'd known in advance what we had to bring along, it would have helped us. We had breakfast in the apt each morning.
The layout of the whole resort is a little complicated. The promenade is nice but it is long in terms of a walk to reflections pool. On the road side it is more complicated and no
Reviewed on Aug 4, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,912, price is now $1,191 per person
$1,191
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,007 reviews)
Love it and why we keep coming back!
Reviewed on Aug 4, 2026


Manasota Key Resort
Save 100% on your flight
Price was $924, price is now $623 per person
$623
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (304 reviews)
Our stay at Manasota Key Resort was absolutely excellent. We stayed in a one-bedroom Gulf-view unit in the main building, and the views were beautiful. The resort was incredibly quiet, clean, and spacious, with plenty of room to relax. The bed was very comfortable, although the sofa bed was not quite as comfortable.
The unit had a huge refrigerator and a fully stocked kitchen with appliances, dishes, and utensils, which made the stay feel even more convenient. The staff was attentive, friendly, and welcoming throughout our visit. We also loved the amenities. Bikes, paddleboards, and kayaks were all included, and the outdoor showers made it easy to rinse off after spending time at the beach.
The location was excellent, and we really appreciated that the resort allowed us to remain on the property and continue enjoying the amenities after checkout. That extra hospitality made a wonderful stay even better. We would absolutely stay here again and highly recommend Manasota Key Resort to anyone looking for a peaceful, comfortable Gulf Coast getaway.
Reviewed on Aug 3, 2026

Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,840, price is now $1,242 per person
$1,242
per person
Oct 17 - Oct 24
found 2 days ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
Housekeeping Cynthia was so kind and super sweet! Poor bar staff was incredible and attentive! Checking in was depressing because the lady clearly didn’t want to be there. We walked in all excited and she was awful and kept making comments to the lady standing next to her at the other computer (wish we would have gone to her instead). Then there was no parking even though we paid for it. We noticed only a few cars had parking passes and the rest didn’t. Then people were hogging 6+ chairs at 7am by the pool which is insanity. So we couldn’t get chairs. We were there all day and barely any of the chairs were being used. We’ve been coming here for decades but it’s changed a lot. Wish they would fix these major issues.
Reviewed on Aug 3, 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! (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

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

Waterfront Everglades basecamp with dock, trailer parking, and direct bay access
Ochopee FL
9.8/10 Exceptional! (21 reviews)
"Great host"
Reviewed on May 23, 2026
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.
Find the Best Chokoloskee Island Vacation Packages
Chokoloskee Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Miami Intl. Airport (MIA) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















