Hello again it's been two years since i last reviewed this resort although i've stayed there twice(spring and fall/winter) a year for nearly 15 years. In fact My wife and i love this place so much we bought 2 weeks here(timeshare) and use them faithfully every year, I feel quite guilty keeping quiet about Caloosa, as it's probably been one of the best kept secrets in the Keys for years and every now and then my selfish guilt prompts me to write a review.so sorry in advance to the other Caloosa fansand here goes.
The views are fantastic from all of the property including the rooms 1 balcony for efficiencies and 2 for suites,
The Safari Lounge is the onsite bar and has some amazing views too, as well as some very welcome and extremely cold beer.
The resort is maintained to a very high standard, mainly by Barry and Ron, which is no mean feat as the climate here can be brutal, and yes some areas of the the main building do show a little well repaired age related patina, which one of us doesnt?
The grounds and pool are beautiful and immaculately maintained and there is ample car parking, and luggage carts, the composite decking is very user friendly and looks good too.
the elevator is situated to the left of the office and is ideal for transporting heavy luggage and shopping:) although pretty much unnecessary most of the time as only 2 floors.
The rooms/suites are always very clean and well presented with everything you need to keep the beer cold and even cook the catch if you dont feel like using any of the excellent eating places locally, just don't expect glitzy Orlando style 5 * accommodations YOU ARE IN "THE KEYS" Trust me in the Keys this is what passes for Really GOOD, Just look out of the window, or sit on the balcony enjoy, unwind and repeat and for pete's sake bring your own hairdryer, if it's a life or death thing for you????
Some people find the old air conditioners noisy, it's never bothered me, however they are gradually upgrading them for newer quieter versions.
My Wife and i have tried many of the hotels and accommodations in the Keys during the last 15 years, and it never ceases to amaze us at some of the places that supposedly rank higher than Caloosa, it's a very hard act to beat, if you know & love the keys then i don't think you'll be disappointed, just don't come too much as it makes it more difficult for us to get an extra few days or a week booked at short notice:) only kidding- enjoy!
Wi Fi is free and recently upgraded
and surprise, surprise there are bugs in the keys, although you rarely ever see one actually in Caloosa, there are also small lizards running about outside, and if you get lucky maybe a land crab or iguana, or even a Manatee in the marina.

I’ve also included my 2009 review below and just updated/added any bits you might find useful,

Look for the big rhino advertising the on site and extremely friendly bar "Safari Lounge" as you drive down the keys its around MM 73.5ish
If you are looking for pretentious nonsense, then Caloosa is not for you! if you want cheap and cheerful(not a lot left in this area) then its still no and if you want to pay through the nose for some dressed up vintage motel then Caloosa is not for you either, if you want a location that is up there with the best the keys has to offer, in a friendly well maintained resort with friendly helpful staff ( The Ladies in the Office will look after you especially Betty and Dusty) with a proper marina on your doorstep(right next door to “Channel 2” Tarpon Heaven) then this is the place for you!! and you'll probably love the place as much as we do
best breakfast approx 10 miles north and well worth it’s still Mangrove Mikes although they do fantastic lunches too
Best Dinner same direction Tower of Pizza, not much to look at but if you like Italian- the Fooood is superb(not exactly fancy just real good)
up and coming restaurant on site at Caloosa Habanos, Habanos has been increasing in popularity my experience is limited but reports are good.
On site Gas station/tackle bait shop and a separate Hardware/Marine store
Best tackle shop around still World wide sportsman (Bass pro) and they have an Islamorada Fish company restaurant on site and the Zane grey Lounge for a Beer while the sun goes down,
Good steak at Outback Steakhouse(Hampton inn)
Marina facilities onsite from Caloosa Cove Marina although they stopped hiring out boats some time ago
Charter boats on site
check out the tarpon at Robbies marina- you can feed them too just watch out they can JUMP(webcam)
Hope i'll see you there
ps my only negative point, they recently replaced a lot of the beds with really SOFT mattresses and they take a bit of getting used to, going to bed can be a little like throwing yourself into a really big super soft marshmallow, once you get used to it it's ok and if you like a soft bed you'll probably love it,