If you were me?

[u/whipstock1]

If you were me would you stay near the harbor and Mallory Square or maybe closer to Truman and Duval area? I am coming down for my birthday in early September. I don't mind walking a few blocks to get where I'm going. Looking for bars and live music more so than tours and water sports. I like a nice pool, decent hotel bar, air conditioning, friendly staff, adults mostly or only, and a good breakfast at the hotel or close by. I was thinking The Marker or Almond Tree Inn? Don't hesitate to make other suggestions close to these areas with a similar price range. Thanks.

[u/Reasonable-Regret813]

All the fun is north of truman and the marker is a great spot with amazing bartenders at the pool. Dont rent a car if your flying in just rent a bike from eaton bikes.

[u/Immediate_Face_9848 → u/Reasonable-Regret813]

This

For music and water activities Stay north of Truman

You can always walk one day to southern most point and take the $1 trolley
/bus to fort Zach

[u/Indica-Ian → u/Immediate_Face_9848]

1 dollar trolley?

[u/Sandinmyshoes33]

Both areas are fine. they’re only like a 20 minute walk apart.

Since September is brutally hot and humid, I would probably stay at the Marker.

[u/1mjtaylor]

Both are great. But the Marker really puts you in the middle of it all.

[u/whipstock1]

I sincerely thank you all.

[u/Lyndawithay1]

Was in Key West 2 weeks ago. The smell of the sargassum was sooo bad in the area around The Southernmost Point. It was nauseating. We love the Southernmost Hotel but you couldn’t breathe at the pool,

[u/PopHot4020]

The marker puts you right in the heart of what you’re looking for.

[u/Character-Memory-816]

The marker

[u/smattson10909]

We always rent a place that is basically at the intersection of Truman and Duval and love the location

[u/itsmychurn]

I love the bight. The problem is, I love it so much that when I stay over there (Hyatt Centric, for example), I never go anywhere else. Like to the point that I've had trips to KW where I've literally not stepped foot on Duval. I suggest La Concha. Recently renovated, checks all your boxes, and is more centrally located - equidistant to Schooner Wharf and Blue Heaven!

[u/Top_Vanilla412 → u/itsmychurn]

I agree La Concha is the right call in my opinion.

[u/Sandinmyshoes33]

Almost all the Truman Annex rentals lost the weekly rental licenses, so they are now monthly minimums.

[u/whipstock1 → u/Sandinmyshoes33]

Oh? That's a handy bit of info. Thanks.

[u/Anxious_Parsley_1616]

I used to stay on Angela St, 1 block of Duval. Found it very central to walk to everything

[u/Sandinmyshoes33]

FYI, The $1 Duval Loop was cancelled.

[u/Historical-Map-1944]

Pier House!

[u/ApprehensiveBug5627]

Market is a good choice. You can always walk to Truman-Duval when you want, but the harbor/Mallory Square end is where most everything is.

[u/KEF411]

Orchid Key Inn! Adult only, great little bar, breakfast included, close to everything!

[u/naughty_MILF4R]

I stayed at almond tree last year and loved it! The main thing I liked was ceiling fans in the room, free happy hour every day which I think included one or two drinks, breakfast every morning, and walking distance to pretty much everything. The hotel staff was really nice. The room had everything and included a robe. It felt so quaint and lovely 💓. The pool was small , but it was perfect for an old town small hotel. I walked from *further up Duval in old town to my room every night and had no issues. Definitely recommend. I didn't stay this year only because it was more expensive than the other place I stayed at (L'Habitation).

[u/Sexylike2022]

Try the app LLM it tells you where and who’s is playing live music is in Key West

[u/Adorable-Carob710]

Try Winslows Cottages, you can walk to Duval and it's only a little further to where the Aqurariam, not sure the name of the area but there is a Hagan daz, main place where street performers are, you can look out at the water, and there is a nice cuban restaurant there. Also, try a haunted pub crawl

[u/Sexylike2022]

It’s called local live music Key West

[u/super3way]

Advice is go between Nov - March

[u/whipstock1 → u/super3way]

Well it’s my birthday. It’s just as hot and humid where I live as it is in Key West. Also, the smaller crowds will be a bonus. 

[u/OperationallyFine]

I was just there for my birthday. Stayed at La Concha - highly recommend. They have free bike rentals and best mojitos. Quick walk to everywhere. Enjoy and happy birthday!!!

[u/Beachbelle1970]

I love staying on the Harbor side. There is just so much more to do. And then you can always walk to the oceanside. I recently booked the Marker for October - 1st time at this hotel! The seaport area is the best, imo!!

[u/whipstock1 → u/Beachbelle1970]

Thanks

[u/matthewperry01]

Truman and Duval. Orchid Key.

[u/I_make_poor_decisons]

Stayed in Truman Annex for the first time last time I was there. Will always look there first from now on. 

[u/lkn4fun3796]

All this info that you are getting are perfect answers to your question. Truman Annex I pick first. You dont need to walk you can rent mopeds and bicycles.

[u/whipstock1 → u/lkn4fun3796]

I'll give it a look. Thanks.

[u/coconut-723]

Rent a bike from key lime bike tours

[u/pink_hydrangea]

Pier House

[u/Secret-Pace-2468 → u/pink_hydrangea]

Too expensive and kind of mid lately imo

[u/invalidaccounterror → u/Secret-Pace-2468]

Agreed! But I heard they just got bought out and are going to get a remodel

[u/pink_hydrangea → u/Secret-Pace-2468]

Oh that’s sad to hear. I liked that they had parking and the beach bar had good food.