
Chokoloskee Island Vacations from $750
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The Latest Chokoloskee Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Landing Apartments Fort Myers - River District
Fort Myers River District
Save 100% on your flight
Price was $1,067, price is now $750 per person
$750
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (2 reviews)
Apartment was clean and comfortable. The location was perfect. Walking distance to restaurants and café shops.
Reviewed on Mar 24, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,923, price is now $1,024 per person
$1,024
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
The only disappointing aspect of our stay was an interaction at checkout with a front desk employee named Autum. Unfortunately, her demeanor came across as rude and condescending, which is especially disheartening during an early 6:20 AM departure.I had a simple question regarding the valet charges, as we were billed twice despite the car not being moved. It felt somewhat misleading, as “valet parking” typically implies an active service, rather than a static parking charge over multiple days. Rather than offering clarification with professionalism and understanding, the interaction felt dismissive and unnecessarily unpleasant.I shared that the front desk experience is both the first and last impression of a stay, and it truly sets the tone — which is why a more gracious approach would make such a difference.That said, I still felt it was important to leave a five-star review because the manager was exceptional. He handled a minor issue with our room lock with care, professionalism, and genuine attentiveness. His level of service reflects the standard the resort deserves to be known for.Overall, this is a beautiful property, and I would absolutely return and recommend it to friends and family. My hope is simply that all guest-facing interactions reflect the same level of excellence demonstrated by the management team.
Reviewed on Mar 29, 2026

Marriott Sanibel Harbour Resort & Spa
Punta Rassa
Save 100% on your flight
Price was $1,366, price is now $905 per person
$905
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,013 reviews)
I liked the stay very much, hotel is in great conditions yet there are some things that should be pointed out, because for the price you should expect a better service, in example: Valet. The entire valet staff was great except for one gentleman that seems to talk to you with authority which somehow makes you feel not welcome upon arrival. I’ve never received that kind of attitude from any of the Valet staff from any other Marriot hotels that I’ve stayed at. Another thing to point out is the cleaning. There should be bags in the bathroom bin. Yes! That one bin right next to the toilet where you dispose of your dirty stuff. That was unacceptable to me nor the fact that in 2 days that I was there, not one time was cleaned by the cleaning crew. Also, there were spider webs in the balcony and bird poop on the balcony furniture. Third but not last, there should be a lifeguard in place at the swimming pool, due to the fact of plenty of tourist families that come with their children, which at some times may get distracted and some accidents may happen or some irresponsible guests having drinks in the pool, maybe some couples which are having sexual behaviors, that are inappropriate in front of children. These are some minimal things that require a lifeguard in a swimming pool, especially if it’s in a high season!
Last observation with a bad review is the SPA. This SPA should extend their schedule as well as their staff. It is overrated for the price, attention and staff.
Reviewed on Mar 29, 2026

Landing Furnished Apartments Immokalee Road - Naples
Rural Estates
Save 100% on your flight
Price was $1,327, price is now $933 per person
$933
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Fort Myers (RSW)
No reviews
When we finally open the door, it was late, we were tired, there was a terrible smell, but the lay out of the place looked nice. We went out to eat , when we came back and used the bathroom sink a strong smell of sure came out, also when we flushed the toile and the next morning when I shower a strong sure smell came out. The toilet run all night, the refrigerator was very hot. I called Landing to complained about it and said I was going to contact Expedia and ask to be relicated to a hotel for false advertising, they send maintenance around 10:30 am. Maintenance explained that those things happened when the unit is not in use continuasly. They flushed the water heater, fixed the toilet, try to fix the refrigerator, with no luck, they end up bringing another refrigerator. After a three hour ordeal they left and the smell wasn’t there any more.
Beside that the place was lovely, great location, 2 great restaurant in walking distance, well light. The maintenance supervisor of the building complex was very profesional and apologetic.
Reviewed on Mar 25, 2026
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Deep Water Access with a Panoramic View of Chokoloskee Bay
Chokoloskee FL

Waterfront 2 bedroom 1 bath with boat slip
Chokoloskee FL

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
Chokoloskee FL
9.6/10 Exceptional! (133 reviews)
Everything was fantastic. if we had any questions or any concerns, the owner responded right away and helped us out. we would have loved to stay longer, but unfortunately, Weather wasn’t on our side.. the people that were around that place were awesome very friendly polit…
Reviewed on Nov 30, 2025
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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Chokoloskee Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Miami Intl. Airport (MIA) |
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