I second the Bed and Breakfast idea. It's possible that you can find better deals on BnB's than hotels. If you have a smart phone, you can use an app called Airbnb to search almost any city for different setups and time frames. Good luck!

 

Thanks guys, got one.... 286 a night but very nice, hell you only live once

Be Safe, JIM

 

Check out Southernmost in KW in Sept and early reservation you should be able to save $$$. Hampton Inn in Islamorda in off season should be great deal. Usually stay at Navy Lodge or Temp Q being Retired US Army the rate is the best for me but only available to active then retired on a space available.

 

G/F and I just got back from Key West. Stayed in little house called Jasmine house. 1 Block off Duval. Center Street. It was a room with little fridge and a coffee machine but was about $175 per night. Walk everywhere. Off street park at church next door ($10 per night). Only there to sleep and shower so amenities didn't matter. Great place to spend my B-Day.

 

Look into a Bed and Breakfast we stayed here a few years ago and would recommend it.
http://www.oldtownmanor.com/

But it looks like they are booked that weekend.

 

I have a solution for you. Look up Stephanie under "Floridakeysgirl.com" This girl writes a blog about Key west, she is a travel agent and she is a good friend of mine. She has a house down there and I see her weekly. I can tell you if your looking and have not booked she is the one to go to. She will get you the right place at the right price. Talk is cheap so give her a shot. Better to deal with someone that is local and writes about the island then a computer.

 

Right on,, we are frequent flyers there you will spend and extra 450,but its worth it !

 

We are in Marathon and I was gonna say good luck finding something in Kw for $150 a night. I dont think I've ever seen anything for less than $200 a night that I would recommend staying in. We stayed with a friend last year at the Navy motel and that was like $80 a night for military. We were just down in KW last week and I saw that 3 of the "cheap" hotels along Roosevelt as you come on the island were gone. gone as in demolished. I think it was the Econo Lodge, Days Inn and one other one. By you saying downtown I'm guessing you mean "old town" as on Duval. I guess I'd have to go with the others and say look into a B&B. Let me know if you would like me to check out a place for you that you find. I should be down there a few times in the next couple weeks. Good luck!

 

It really depends on the season/ holiday/ event. I have gone down in October and stayed in really nice places for 139 to 149 that during the poker run are 325. They get what the market lets them.

For me I visit the keys often staying all over from Key Largo to KW. I have heard about the Poker Run for years but could never get the time to go, This year I can and can't wait, I will just have to pay a little more..... LOL

Be Safe JIM

 

Like everybody has already said, you will be lucky to get a paperbag to pull over your head for $150.00.

We rode down once three years ago; DEFINITELY check KAYAK or other sources for other events happening!!

Such fools we were! We went on the week of University of Miami's graduation and tried to get a decent room in Miami after a day on the road from north of Orlando.
We did eventually, but then on the way down the Keys there was a friggin' relay foot race all the way down!!

Rooms, restaurants, and even open road was choked by runners and their chase teams!!

We did make it, and were lucky to get in a dumpy motel for around $275.00 a night on the north side of everything.

Everything got better after a few drinks at Sloppy Joe's, and now we can look back and laugh at our poor planning and luck such as it was.

Good luck and let us know how you made out.