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How to get a FREE Hotel or Airbnb in Key West

(disclaimer : This was not planned, it is not recommended, and we did not stay in the Airbnb)

I’m honestly a little skeptical to share this with you guys. Not because I don’t love sharing how to get good deal, but this, my friends…. I wouldn’t exactly consider a good deal. Seeing as we almost got arrested. I'm really swallowing my pride to fill you guys in on this crazy night.

After a long day of bar hopping on Duvall St., (because what else is there to do in Key West?) my friend Taylor and I decided we wanted to do some star-gazing. Not really.. we just didn’t know where to go and figured laying on a pallet made for a better time than freaking out about “what now.” Plus, we had already been basically kicked out of the strip club.

(yep. we almost fought a stripper)

We had never been to the Key’s before, and were not very familiar with the area. All we wanted was a good spot to lay a pallet, while we rest a bit and figure out where we would stay for the night.

We drove for a while, discussing different options, and we agreed on a spot aside a bridge, where there were several cars parked and people were night fishing.

I mean… this seemed ok? There were cars, and people and music…

We didn't think anyone would be bothered by our pallet.

After sitting on our phones for a while, not paying attention to our surroundings (or discussing where we would actually sleep), I looked up to realize we were now the only car left.

Before I could even complete my sentence “Tay, did you realize we are the only ….”

Two police cars pulled up. GREAT! But hey, no longer alone out here.

We sat in silence, unsure of what to do, just kind of looking at each other & waiting.

We are really good under pressure, can’t you tell?

They obviously spotted my car and the beer bongs in the backseat before they found us lying on our pallet. Of course they shined their flashlights all in our faces and proceeded to tell us we could not “camp” there. We explained we were not camping, just hanging out looking at the starts. They did not like (or seem to believe) that answer, especially the lady cop. They also didn’t believe that we had been casually walking up and down Duvall St. with a beer bong in hand all day. WELL WE WERE, OKAY?!

& now we are just hanging out, not bothering anyone. OKBYE!

Now we weren’t DRUNK by any means (or wouldn’t have drove there, duh) ..

but I was in no place to argue with a cop who suggested we call an Uber or Cab back to our hotel.

This is where shit gets tricky!

You see, as mentioned, we actually came there to decide where to sleep

and did not actually have a hotel room for that night.

Good thing we knew a little about the hotels in Key West (from searching and booking other nights) when the police were interrogating us about where we were staying, how much we were able to get the room per night, etc. In a panic, we told them we were staying at the Best Western, and that an Uber was on the way. We literally had to sit there and download Uber, which had only been in Key West for about a week, come to find out.

Of course the police waited there with us until the Uber arrived, which actually made for some good conversation. The male cop was very polite , social, and told us some interesting facts about Key West.

The guy even provided his card with his cell phone number and told my friend she had a “free pass” for her birthday. Meaning, if she got into any trouble while we were here ON HER BIRTHDAY ONLY, we could call him (after 12pm) and he would take care of it. (loorrrddd, what has he done)

When the Uber finally arrived, after what seemed like lifetime, we were faced with quite a challenge. We had the destination set to Best Western, but didn’t actually have a room there. I also made a HUGE deal about leaving my car on the side of the road so the cops said they would “watch it” until the end of their shift (8 am). Meaning we couldn’t have the Uber driver circle around and go back to get my car

(why do I do these things to myself).

The Uber driver dropped us off at Best Western, all we had were some clothes in our hand, our wallets, and our cell phones, which were ironically dying! Of course, we tried to get a room at the Best Western, where we were stranded & OF COURSE they were booked.

If you know my life at all, you probably guessed this would happen. At that point, we googled nearby hotels & set out on foot. The closest hotel was about a mile away (“we can do this! we will figure this out” We said). aaanndd Yep! You know it – they were booked as well.

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With now dead phones, completely exhausted - we trekked our way to one last hotel, which was OF COURSE past our starting point, in the OTHER DIRECTION. I knowwww – the misfortune, right?! (we were hanging onto “Third times a charm” hope for dear life)

Now, let me go ahead and skip to the point where, yes, the third hotel also had NO VACANCY!

How were we even going to request an Uber back to my car? (with dead phones)

We literally laughed at life at this point. It was sometime between 3 & 4 am and all we wanted to do was lay down. Even the pallet would have sufficed. We walked outside of the hotel door after being let down, and just sat. Right there. On the steps. And laughed.

Because its better than crying, right?

While we were sitting there, a taxi full of people our age pulled in. We were so excited! Since we couldn’t use our phones, this was our chance to catch a ride back to my car. The group of people, however, asked us if we were about to “go out.” To which we replied sarcastically “yeeaaa, going out.. at 4am. Woo!” They didn’t catch the sarcasm and were trying to join in on our “fun.” HA. We then explained our last few hours, and out of pity, they offered us their pull out bed in their hotel room. THERE IS A GOD!

Yes, this was kind of risky, but OH MY GOODNESS we were being offered a bed (for free) after this wild goose chase for one. We stayed up for a bit, getting to know these people (mainly to make sure they wouldn’t try to drug, rape, or kill us while we were asleep). We eventually passed out, on OUR OWN BED.

*queue the angels singing*

After using their bed & phone charger, we were able to get our lives together enough to call an Uber back to my car. $35 later (to & from) we finally made it! Now what? Lol. It was 8am, we still had no hotel, we were still exhausted.

My friend napped the whole Uber ride to the car & it was all I could do to get her out of that car, into mine. The morning Uber driver was really cool! He gave me a map, told me some cool spots to check out, even showed me where he lived (on the water!).

“don’t tow or ticket” When we got back to the car there was a nice note on the window sayingwith the Police Officer's badge ID number. Well, at least there's that... and my car was still there.


While Tay finished napping, I called every single hotel in Key West (at least that’s what it felt like) trying to find a hotel that we could check into RIGHT THEN! I called at least 8, before I finally lucked out. I woke Taylor up whenever we pulled in. It was her birthday weekend and I was determined to figure this out.

I ended up getting a room at The Perry Hotel on Stock Island. I even got a discount with my AAA membership. I’m not sure how things turned around so quickly, but wow! We went from: a roadside pallet, to walking the streets with dead phones, to a strangers pull out couch, to a luxury hotel. LIFE! So neat. So full of roller coasters.

I may write a separate post for the hotel

We were the definition of exhausted and decided to get some rest. & OMG THE BEDS!

Aside from trying to find one all night – I kid you not, that was the most comfortable bed I’d ever laid on. Regardless of if it was from exhaustion or comfort, we basically slept that whole day away.

The most we slept the whole trip!

When we eventually got our lives together enough to head back to Duvall St (what else) we looked back at the note left on my car and laughed about the crazy night we had. Then we see the back………


Although we could have saved nearly $300 on the hotel room & stayed in the Airbnb,

we had such a great experience at the hotel. (Plus, we needed somewhere to go at 8 am)

Robes, full size bottles of essential oil bath products, hammocks by the pool, 3 bars… need I say more?!

Would you have stayed in the Airbnb offered by the Police?

♥ Haley Jane

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