Where to stay in Key West in early May?

April 3, 2019 4:21 PM

Two adult women (mother and daughter) planning a 5 day getaway, May 6 through 10. We would like to be walking distance to eateries and sightseeing.

Both like architecture and gardens, walking, beaches. A pool would be a nice perk. Don't want to spend a ton of money, but realize that it's not going to be cheap. Open to smaller hotels, bed and breakfast, airbnb..just want a quiet, clean place. Prefer 2 beds, can be in the same room, but a king would suffice. Any recommendations will be gratefully accepted! Old Town Key West would be perfect, but where do we stay??

posted by LaBellaStella to Travel & Transportation around Key West, FL (7 answers total)

Best answer: It's definitely not cheap (we stayed in the cheapest room and it was, IIRC, close to $300 a night), though in any case "cheap" didn't seem to be an option when we were in Key West -- but Simonton Court was so nice. Super beautiful grounds, nice pools, pretty rooms with comfy beds and big porches, and very quiet, within a block or two of all the stuff. We had a car but we parked it after check-in and didn't use it again while we were there.
posted by goodbyewaffles at 4:34 PM on April 3, 2019

Best answer: First, I'd be wary of Airbnb in KW because the city prohibits it and there have also been scams where people claim to represent a property that isn't even theirs.

My family is associated with the Ambrosia Guesthouse, so I'm partial to it, but I've had friends stay at the following places and they've said good things: Island City House, Artist House, Eden House (lots of houses, I know), Not Your Average Hotel (this might be more of a hostel).

A good friend of mine also runs a travel planning service in KW, so I'll bet she could also give you recommendations: https://vacationkw.com/. She's great and very knowledgeable about the town.

May is a good time to go because it will probably be less busy and maybe some of the hotel rates will be a little less expensive.

Have fun!
posted by 6and12 at 5:19 PM on April 3, 2019

Response by poster: Thanks! This is so helpful!
posted by LaBellaStella at 5:08 AM on April 4, 2019

We stayed at Old Town Manor a few years ago. I don't remember it being cheap, but it wasn't terribly expensive either (IIRC, it was significantly cheaper than our South Beach hotel), and we stayed in one of the larger rooms. The location was just about perfect: far enough away from Duval street that you didn't hear the noise at night, but close enough that you could walk there if you wanted. No pool, though.
posted by Comrade_robot at 5:14 AM on April 4, 2019

Not your Average Hotel is definitely a hostel. I don’t recommend it to folks over 30.
posted by mrfuga0 at 6:43 AM on April 4, 2019

We stayed at Papa's Hideaway through VRBO and it was lovely. Also, The Merlin is gorgeous and both places are in the perfect location for parking your car and walking everywhere.

Enjoy!
posted by kiwi-epitome at 7:54 AM on April 4, 2019

I've only been there once, a couple of years ago, but we stayed at Courtney's Place and found it lovely and convenient.
posted by Occula at 8:24 AM on April 4, 2019