I and my 2 daughters,ages 24,and 15, hope to spend 3 nights on KW and would like recommendations on lodging.

Prefer a smaller, hotel, inn or B&B with a "Key West" feel.
Don't want a resort like the Casa Marina or Hyatt
In the historic Old Town, near Duval...but on the quieter side.
Swimming pool a must

Any advice is greatly appreciated. I had really wanted the Gardens Hotel, but they have an age restriction(>16y/o) and were not willing to make a concession.

Thanks, everyone, for your input.

Can't help you with hotel recommendation, but since you are traveling with your kids here is a little warning. Do not go there between Oct 18-27 because of FantasyFest. Great deal of public nudity, street drinking, etc.

Actually, we're planning to go mid-June of the year. Hopefully, things will be a bit tamer then!

Check out Island City House...should be what you are looking for....

We stayed at The Conch House a few years ago and like it a lot

http://www.conchhouse.com/

DH and I stayed at the Southernmost Hotel a few years ago and enjoyed it. The branch Southernmost on the Beach has a pool, according to their website. I think the site said they were finishing pool renovations this month, so call to ask before making a reservation, if you decide on it. It is definitely on the quiet end of Duval street.

try www.keywesthistoricinns.com

Check out www.tropicalinn.com

Southernmost, while fine for frequent visitors is at the opposite end of Duval away from where all the action is - I'd look into the Marquesa or Pilot House.

The Butterfly Observatory is a must see! Smathers beach and the state park (Zachary Taylor?). You may know this but expect the temps neat 90 with s breeze and pm thunder showers. You can rent jet skis to go around the island, parasail and snorkel. For the trip of a lifetime get on the ferry to Dry Tourtugus!!

We stayed at
http://www.orchidkeyinn.com/ on Duval but a 10 - 15 minute walk to Pier House, so its on the quieter side.
We enjoyed.
We rented bikes that we kept overnight locked up at the hotel to get around the island without having to worry about parking and driving. There was a bike shop very close by.
On word of caution on the bikes - you need to have a light to drive it at night or you will get a ticket. Make sure to rent a light.