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We stayed at the Southwind Motel a couple years ago. It was just ok. It was a great location! But the roosters made it VERY noisy starting at like 3 or 4 am. I know the price was good when we stayed there, that is why we choose it. But it was outdated and not the cleanest, but not horrid either. It made for great stories we look back on now and laugh :)
I stayed here during my minimoon after my first wedding years ago while living in Miami and getting married in Islamorada: http://www.ambrosiakeywest.com/keywesthotelaccommodations.htm It was great! It was almost 10 years ago, but great value and the room was super nice.
If you have time, spend a night at Holiday Isle in Islamorada - SO much fun!
Price and location are our main concerns. We don't have a ton of money to spend, and we aren't having a rental car while we're in Key West so we want to be able to get most places on foot or bike.
If you want to be in easy walking distance to most of the nightlife and attractions, I recommend choosing something a little farther north (north of Truman) - like the Wicker Guesthouse (I stayed here many years ago and liked it) or the Merlin Guesthouse or even closer to the northern end of Duval. I would check the reviews on TripAdvisor to make sure you get a decent place - there are lots to choose from in Key West, and some can be a bit rundown. Good luck and have fun!
Be sure to go to Blue Heaven for breakfast one day. :)
I love Camille's for breakfast. Honestly in my opinion, you can walk up/down Duval St from end to end, so I don't think any side is really a big deal.
I personally prefer the quieter side (Southernmost Point) and that hotel and the Hilton are gorgeous! But they might be pricey.
@abbyful: Did you choose where you are going to stay yet? We stayed at the Santa Maria resorts http://www.santamariasuites.com/
Not sure if it's in your price range, but we LOVED it! If you can't stay there, at least eat at the resturant attached to the hotel, Ambrosia.
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I've found a bunch of possible hotels/motels, guesthouses, and B&Bs in Key West that we can potentially afford for our honeymoon.
What part of the island is best to stay in?
Here's the possible lodging I have on my list: http://maps.google.com/maps/ms?ie=UTF8&msa=0&msid=215493264913155714363.0004a1c743ded24ad8fee&ll=24.55778,-81.792483&spn=0.031031,0.066047&t=h&z=15
I was thinking of choosing from the southernmost hotels I've marked, has anyone stayed in any of these?