Key West is home to as many hotels as it is rum bars. For a small island town it has a hell of a lot going on, and a good few nights stay is definitely necessary for making the most of it. But how do you choose one hotel from a whole host of different kinds and price points online? Out of everywhere I have stayed I initially found Key West the most confusing when it came to booking a hotel.

These are my must read tips for choosing and booking a hotel in Key West.

Tip 1: Modern or a Dash of Original Key West Charm?

Iconic hotels such as the historical Southernmost House will make your stay very memorable, whereas modern new builds, such as The Gates are Instgram-ready. I personally love the older buildings with more history, especially those that have been restored with antiques and original items.

tips booking hotel Key West

The Iconic Southernmost House

Tip 2: Duval or Not Duval, That is the Question…

There are lots of hotels located on the main street Duval, or just close by, within walking distance. This is perfect for being right in the heart of the city, and being close to restaurants, bars, and shops. However if you have more of an escape in mind you might want to book something outside of the old town, ocean facing. This tends to be the resorts. One of my favourites which has an amazing quiet courtyard and pool despite it’s location in the heart of Duval street is the Duval House (read about my stay here).

Tip 3: Choose Wisely: Boutique or Resort?

This depends a lot on the last point, but could also make your decision for you. There are quite a few of the more luxury resorts in the old town, whereas your mid-range ones tend to be in the ‘new town’ – about a ten minute drive away. Your decision here really depends on what kind of stay you are going for. If you are more of a room service and lounge by the pool kind of person, I would recommend a resort, but if you prefer to get out there and do your own thing, the boutique hotels are wonderful.

tips booking hotel Key West

The Lovely Traditional Rooms At The Duval House

Tip 4: Kids or Adult Only?

A lot of the hotels and guest houses are adults only, and some are more family-orientated. You can even find gay only hotels if that is your thing. Make sure you check the details before you book to avoid any issues when you arrive.

Tip 5: It’s Freaking Hot, You Might Really Need That Pool…

If you are a Keys newcomer, you might be surprised to find that there aren’t actually that many beaches. Key West is home to a few, but you will most likely be very grateful of having a pool when you get there. Of course the resorts have pools, but you will also find that a lot of the smaller guest houses also have nice size pools at the back. It is definitely worth making sure your hotel has one either way, after an hour strolling down Duval you will be desperate to jump right in.

tips booking hotel Key West

The Gates Hotel (via

Tip 6: I Don’t Really Give a F**k, Just Give Me The Cheapest…

In this case, it really depends on the season. Right now, for example, there are some fantastic deals which will probably continue for the rest of the summer until October when rates are hiked back up. During peak season – October through April, I would recommend either one of the hostels (don’t get excited, they’re still relatively expensive) or doing a secret deal on

tips booking hotel Key West

The Local Beach – Small, and Pretty Crowded

Tip 7: Where To Book

I always compare hotel prices on a few different websites. Also, be sure to check the specific hotel websites too. For instance, I just booked the Southernmost House and it was considerably cheaper booking direct with their summer deal than it was on various booking websites.

My favourite booking websites are as follows:

Secret Escapes

Such a good booking website if luxury-for-less is your thing. I love scrolling through and seeing all the wonderful deals they have. Plus, get $40 free credit via this link.



For my full booking resources guide click here.

Coming Soon: the full comprehensive list of Luxury Backpack’s favourite hotels in Key West.

tips booking hotel Key West

Smiling because I got a good deal!

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tips booking hotel Key West

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