Is there any chance of finding an affordable place to stay in old town Key West this coming January or Feb if I book early? We stayed in new town key west last year, and I wouldn't want to repeat that again. Recommendations for places to look into, hopefully keeping the per night cost to $100 max.

I would definitely attempt to avoid Key West Race Week, which is in mid-late January. My parents go every year and it is a madhouse. Prices will definitely be higher then.
Sorry I don't have anywhere to suggest-- I've only stayed in a hotel once (Wyndham Casa Marina) and wouldn't recommend it!

I don't think you will find any deals by booking early. It never hurts to ask though. Doing a quick look at places I know of (but have never stayed), the Angelina Guest House has rooms with a double bed and private bath for $99.00 in high season. It gets good reviews on Trip Advisor, but I know it isn't fancy. I've walked by many times, has a small pool and appears pleasant.

Last time we were there another couple decided at the last minute to join us and had difficulty finding a room. They ended up at a place called Eaton Manor (not Eaton Lodge). Their room was very, very small, but clean and the place was cute. Their web site lists rooms startng at about $80.00 for high season. If you really aren't going to spend any time in your room, this place could work. Keep in mind that these are probably 2004 rates, I doubt 2005 rates are published yet. I'm guessing there are other possibilities. The web site I use is http://keywest.com/ and has a huge listing of accomodations with direct links to the properties' own web pages. Happy browsing!. Jean

I think Eaton Manor has been sold. Either that or Eaton Lodge was sold.

Good luck finding something under $100 in Key West during peak season. Let me know if you do because I'm also looking.

January and February are peak season months, so you won't be able to find anything inexpensive by trying to book early. $100 max in Old Town will be difficult, but try keywestinns.com

There are a number of Key West lodgings that you can get through priceline. The best way to bid on hotels through priceline is to go to a site such as www.biddingfortravel.com and read up on it.

I'd be afraid bidding on Priceline that I'd end up in one of the chain hotels, and probably not in Old Town. To me, that would defeat the purpose of coming to Key West. Jean

Last winter, I didn't see any hotels in old town that went for under $100 per night.

What is the Southernmost going for at that time?

The good thing about biddingfortravel.com is they keep a list of the hotels that have come up through bidding. Who knows, there may be at certain quality levels, only independent hotels. Of course Priceline could always put in a new hotel, but at least with biddingfortravel, you can get a fairly good idea of the hotels you will get. It definitely is true that if you absolutely can't have some time of room - such as one in a chain hotel - then priceline is not for you. I've never had a problem getting non-smoking, but I have heard problems about people bringing 4 adults because when you bid on priceline, it's only for 2 adults (and 2 kids I believe) per room. Usually it's OK but I just read a story about a hotel that enforced this rule....

I just went to the biddingfortravel web site and there are no hotels listed under Key West that aren't chain properties. I know that occasionally some people have gotten other properties, but I'd bet the odds are slim in high season. Jean

Totally agree with Jean H., you want to stay in Old Town. A friend booked through Priceline on our last trip and ended up way out by the airport, had to rent a moped, and ended up speniding more per day than some of the options in Old Town. I don't think booking early has an impact on your rate in Key West.