My husband and I will be in Key WEst for just two nights in August. Looking for a place to stay < $150/night. AFter reading past posts and checking with the properties, I think I have it narrowed down to the following

La Pensione
Chelsea House
Center Court
Simonton Court
I think all of these are close to restaurants, bars, shopping?
Would appreciate any advice or if there is somewhere else that you could recommend I would be grateful. Thanks

Cindy

we camped at leo's campground for $20 and it was great ... i know you're not camping, but a lot of people don't even know there's a nice little place for it in key west

Cindy - based on location alone, I think Simonton Court is the far superior choice. Your other 3 options are either on or very near Truman Avenue, which is a high traffic road.
All the sunset celebrations and most of the restaurants and tourist activities center around the Gulf - much closer to Simonton Court. I've never stayed there but have heard lots of nice comments about it.

Just realized I left out an inn - Ambrosia House. Please comment on that as well thanks
Cindy

Ambrosia House gets very good reviews, too. Simonton Court is a couple of blocks closer to the Gulf, but I think you'd be pleased with either.

Just returned from La Pensione and would never go back. We were in room 9 which is the most requested and still don't know why. The balcony is shared with 2 other rooms which offers no privacy. Bedding was stained and the blinds kept out no light. The noise was 24/7 and the owners and staff were downright rude.

The only thing I would keep in mind with Ambrosia is they are pet friendly, that always makes me nervous. Do you or your hubby have allergies?

We stayed at Simonton Court last year and are returning this year. We loved it and the location is great!

The original post was from five years ago...I'm thinking they have come & gone by now...

I've lived in the Keys for over twenty years and my business takes me to Key West monthly. We manage a timeshare in the upper Keys so we stay at a timeshare resort, The Galleon, which I would highly recommend, but unless you own a timeshare for an exchange, the rentals are quite pricey. However there are many choices of all price ranges on this little island, and price shouldn't be your only criteria. Do you prefer a standard hotel or a bed and breakfast? Do you want to be near the water or off on a charming quiet little side street, or in the middle of the nightlife action? Anywhere in Old Town you will be within walking distance of restaurants and shopping and bars, so don't worry about that. We used to try out different places that just looked interesting and had some great experiences. Forinstance, the Southern Cross is smack in the middle of Duval Street (the main drag), across the street from gorgeous St. Paul's church and next door to the historical Oldest House. The hotel is old fashioned and simple, and when you hear a scratch at the door, it means that one of the resident cats wants to come in and curl up on your bed. For some this would be awful, for others, heaven. But certainly a Key West experience. And in the evening you can sit on the balcony and watch the Duval Crawl go by below. Another interesting place is the Cypress house, a former mansion built by a ship's captain. The wood is Dade Pine and the boards are all notched and grooved, so the house sways slightly in the wind and has weathered many hurricanes. It also has a resident ghost who is shy but friendly. He just doesn't like unlocked doors and from time to time guests find doors in their suites locked without their doing. The owners put on a great cocktail hour and the atmosphere is very friendly.

So many characters in Key West, and not just the people.