Unless your really enjoy seclusion, I wouldn't stay on Sunset Key. If you are looking for a resort, this place is nice - https://www.oceansedgekeywest.com, but there are plenty of other places to stay on the island. We do a VRBO, but we're usually there 30 days.

Another cool place is https://www.perrykeywest.com.

We typically stay at Southernmost Beach Resort because it's right in the middle of the action but it, too, is a bit pricey. We typically can't stay longer than a few days or we'd do like JP and get something like a house.

Be warned..... If you're going in the month of October, your Key West experience may differ from others.

YouTube "Fantasy Fest Key West" if your interest is piqued.

J

P.S. Be sure you visit Better Than Sex desert restaurant while you are there. It's a trip!

And dont go expecting great beaches, that's not the place for that

The Keys are all about boating. You'll never really get the full experience until you haul a boat down there. Of course, there's great fishing, but also great snorkeling and diving. Just exploring all the uninhabited keys can provide days of entertainment. And then there are the sandbar parties. Hanging out in Key West is fun, but that's secondary for us when we are down there.

Fantastic restaurant...especially breakfast and brunch.
La Te Da

Favorite Bar
Schooner Wharf Bar

Outstanding Breakfast
Pepe’s Cafe

Can't help ya . . . Last time I was on Key West was in 1968 . . . . don't remember much but no commies got past our Hawk batteries.






God Bless America ! ! !

Smoke a J and ride a scooter around the entire place , just chill. That’s what I did last time I was there.

I won a sales contest back in the mid-eighties . There was ten couples that won an all expense paid trip Key West . The travel agency that set it all up , provided a brochure . The brochure advised that at least half the population was gay . I am totally OK with that , ---but when my wife and I showed up at the Marriot Hotel , there was a long dock next to that area , probably 200 feet long and I swear , there must have been at least a hundred dudes , all tanning themselves , making out , groping each other and most of them were wearing the skinniest black thong you'll ever see . I told my wife ---" welcome to Key West "
If you go , try to get into a boat and try the fishing . We went and got tons of snapper and I ended up with a giant Cobia . We had a boat set for the next day to get some barracuda , but a storm blew in and cancelled the trip . There used to be a shop close to the harbor that made " while you wait " sandals . same design , just made to your exact size -- all leather with a rubber sole . They do it in like 5 -10 minutes per pair , the line to get in was like a hundred people .

Key West is a big disapointment unless you go in late October. Hemmingways house specially the cats. Look at their paws ! Lighthouse gives a nice view but a bu=it of a climb if older or infirmed. Bars and restaurants are very Commercial.. Mallory square packed with people close to ea h other *( this was pre covid) . I preffered Marathon. Less crowded , a little less expensive, A nice excursion is a boat ride to an island on 7 Mile bridge to see Flaglers work area when constructing the railway. S K I P the Key Largo Bar. A real dump. You can hand feed Tarpon at one of marathon restaurants. They selll bait right there and some of the tarpon were huge, I'd say get a car but if you only stay in Key west just walk or scooter. It may be less crowded now as this was years ago

I think mid May is the perfect time for Key West, especially for fishing,

Where else can you catch , Tarpon , Permit , groupers , snappers , mackerels , sharks , rays, barracuda , cobia ,within 10 minutes of the dock ?

I usually would book a 6 hour trip, and have caught as many as 14 species in one trip.

Seems like it was 6 miles to a wreck in 160 ft of water, It took longer to get the bait to the bottom than it took to get bit. I caught 3 AJ's in three drops,
each a little bigger than the last, My Captain said " we can do this all day long " , I said , NO we can't, Lets do some thing else.

that is the beauty of fishing the light tackle boats out of Key West Harbor , endless possibilities , I took my Son down there when he graduated
high school, We fished 5 days with 5 captains , never fished the same way or location twice.

good luck

Mo

This is what I want to do for a bucket list trip for my 40th. Can you bring fish back with you? Load up on different types of snapper and grouper would be awesome. That or I'll go out of LA somewhere.

This is what I want to do for a bucket list trip for my 40th. Can you bring fish back with you? Load up on different types of snapper and grouper would be awesome. That or I'll go out of LA somewhere. [/quote]

On one trip , one of the captains was kind enough to clean fish , take home and freeze, ( we had a bunch of Dolphin on that trip) We stopped on the way out of town and picked it up. He told me to put in a cooler , duct tape closed , marked " Bait" on the outside, He said the odds of
it being stolen were less that way.

Many restaurants will cook fish that you catch for a small fee.

If you rent a house or condo , it might have a freezer, Some of the larger lodges would freeze your catch, I would think,

MO

You could also check with bait shops, one one trip , we left fish at a bait shop in Key Largo that had a walk in cooler, picked it up on the
way to the airport

MO

Rockie Martin's nephew is down there and we fish with him and stayed at their rental house last time. We caught so many different species of fish and had fillets for days: black grouper, snapper, etc. It was awesome. Conrad Martin with BooYa Fishing Charters is who we use and he's awesome. We had a great few meals cooking our fish right there at the house on a cast iron skillet.