I am a big key west proponent, but i go there to fish.

Depends on what you want to do, and how tolerable you are for the inflated keys prices. Will you be driving all the way from Miami/FLL? Will you have a car the entire duration of your stay?

There are a few ways to get there via AA and Delta but they mostly go through ATL. AA has a direct flight from Dallas I have not done yet.

Year round, United partners with a regional carrier prop plane provider that can be hit or miss. I've been ridiculously delayed once on that airline - silver airways - and opted to make the drive instead. But I've also done the flight from Tampa and FLL, and it is a pretty cool experience.

But At least part of the year you can fly direct from IAH on United, but I think it is only a short period.

There are a few name brand places that you can use points for, but the Marriott properties aren't walking distance to the old town/duval street area. If you're a Hyatt person, there's a property next to the marina.

If you're balling, ocean key, pier house or the Hyatt are right there in the water at the end of duval. Have done a vrbo/airbnb with a private pool as well off Duval.

Laconcha is a mid rise hotel in the middle part of Duval.

On the south end of key west close-ish to the famous mile marker zero there's a Waldorf property but not my style.

There's the resort type place on sunset key but you have to take a tender to get there which seems like a lot of work.

Lots of little bed and breakfast places you can find online too if that's up your alley. They seem to be rated as three stars but look like they would be fine by me, and I'm sure I will go that route at some point.

There are some great places in islamorada as well. I have to do marathon yet but plan on it in the future.

If you're thinking of driving down the keys from the mainland, you should. Some of it is not great, but you see some really cool stuff driving through the different keys and bridges.

I would check out a visit to Fort Jefferson which is 68 miles West of Key West. Book early.

https://www.nps.gov/drto/learn/historyculture/fort-jefferson.htm

I am a fan. It is not for everyone, but if you don't have a good time there, that is on you. Just bumming around with no real plans or schedule, bumping into small interesting bars, restaurants and shops. Stop and have a beer and some conch whenever you feel like a sit in the shade. You can get in the key west vibe real quick and it is good.

Duval is a better version of Bourban street (by that I mean, much cleaner with better clientele). Lot of history and things to see in town. We did the trip out to Dry Tortugas, it was a long day but memorable. If you can I'd try to stay somewhere that is within a reasonable walk to everything.

With all due respect Noble, we had no idea about Duval, and brought little kiddos with us. What a huge mistake. In my opinion, Key West is not the place for minors...and we did not know that when we went there. Our mistake.

There is a really nice beach at Zachary Taylor State Park.

We took our then 5 y/o to Key West 3 years ago. Had a blast! Stayed at the Blue Marlin, did the ferry to Dry Tortugas, did Hemingway's house, did one sunset at Mallory Square. And as stated above, loved the beach at Zachary Taylor State Park. We mostly avoided Duval Street, especially at night. We did have an afternoon drink at the Green Parrot, and our kid had a Sprite. We saw lots of families.

We'd definitely would go back, and we will when our kid is old enough to dive.

Personally, I like Marathon the best. But that's because I dive.

When I'm ready to quit the rat race, I want to live in Islamorada.

Seaplane to the Dry Tortugas was one of the coolest things we've ever done. Saw dozens of sharks, turtles, dolphin and Tarpon! We aren't big drinkers, but still enjoyed Duval street. The food was good and the key lime pie is great!

Casa Marina. Formerly the Waldor Astoria.

Resort grounds are nice but the rooms are wildly boring/sterile looking online.

Get a nice room at the Marquesa.

If she's a Ritz Carlton only style of vacationer, KW might be miserable to her if she expects Maui. The vibe is flip flops and t-shirts. The person sitting next to you at the bar may be a bum, or he may be millionaire 50 times over. You won't know it by looking at him.

That said - there is absolutely fantastic food in KW. Lots of great seafood and cuban restaurants.

Here in Key West. Neat little island. Love the laid back vib! Just what I needed

I have been several times in the last few years. While the Keys are not known for their beaches, the beach at Fort Zachary Taylor State Park is fantastic, with Australian pine trees providing fabulous shade for the beach and of course there is beautiful water and great people watching. Lots of picnic tables under the pines. Very relaxing and beautiful. Walkable from Duval Street but there is a small parking lot and bike racks there. I like to visit there most every day.

I usually stay near Duval at a place where there is parking and I never move my car. Just walk everywhere. Accommodations are expensive but I usually can find a decent value. Have stayed recently at the Speakeasy Inn (a pretty famous rum bar is on premises), the Casablanca Hotel (has an Irish bar on premises, make sure your room is not too close to it), and the Best Western Hibiscus. There first two are the more authentic Key West type spots (among many) and the latter is more like a motel you would stay at in the rest of the US (nice spot, much bigger rooms, location a bit less convenient). Expect rooms to be very very small as a rule. But that is fine, you spend your days out of the room.

Mallory Square for sunsets and street performers is not to be missed. I usually go there 2-3 times during my several day visits. Buy some popcorn from the old school cart vendor there. He has a blackboard that usually points out it is 17 degrees in Eerie, Pa and 78 in Key West (this is in winter). Key West First Legal Rum Distillery is good to tour and sample rum. There are a few others if you enjoy that.

Lots of great places to eat but I like low-key places like the Waterfront Brewery (near Mallory Square), Ram's Head Southernmost (another microbrew place where it is all outdoors) and many more that do not immediately come to mind. Great food both places and most everyplace in Key West. You want to go to the Green Parrot, Sloppy Joes, and Bull and Whistle but the Rum Bar at the Speakeasy Inn is small, neighborly and fun.

Get a Cuban sandwich at Ana's Southernmost which is near the Hibiscus. They also have a great breakfast and cafe con leche which is to die for. It is all carryout. There is a 2nd location closer to the wharf as I recall. Key West Cuban Coffee on Truman street near Duval has similar fare and fantastic cafe con leche.

You want to try the Key Lime pie. it is good but I am never blown away. Still try, I may be a harsher critic.

The Butterfly Museum is interesting, especially for kids (though as others have said, this is not so much a kid place). The Southernmost point is a popular picture spot but I never wait in long line there for a shot. I have not been to the Hemingway House or the Truman Little White House but can catch those on future trips. Always more to do.

The little train or trolley that goes around town is good to do once so you have the lay of the land.

I usually stay a few days, always have fun and plan to go back soon, maybe in January.

I would surmise that KW could be a little wild on NYE. Not like Fantasy Feat wild, but wild nonetheless.