7 Must-Read Tips For Booking a Hotel In Key West

guide booking hotel Key West

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 gateshotelkeywest.com)

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 hotels.com.

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!

Pin me for later…

tips booking hotel Key West

Don’t forget to follow Luxury Backpack on facebooktwitterinstagram, & bloglovin‘. 

  • Siarra Chantal Turner July 1, 2017 at 3:49 pm

    I needed ALL of this in my life. I’m headed to the Keys in December and I’m definitely saving this for when I book my hotel.


    • Emily July 2, 2017 at 3:05 pm

      Thanks Siarra! Have a wonderful time in December

  • Erin July 1, 2017 at 8:17 pm

    I want to go back to the Florida Keys so badly! Hopefully I can relax there for a week or two after grad school. I’ve looked at hotels and vacation rentals in Key West before, just to get an idea of what’s out there, and it is overwhelming! This post helps break down the choices. Thanks for sharing!

    • Emily July 2, 2017 at 3:05 pm

      It really is overwhelming! Having lived in the Keys for a year and a half I finally learned some secrets, and now know what to book when we stay overnight in Key West – which is pretty often! Hopefully you will get to come back soon 🙂

  • Tracy Schwartz July 1, 2017 at 9:23 pm

    I absolutely love the Keys!!! I’ve stayed in friends houses as well as the resorts and I have to say I like being a little on the outskirt. Exploring and walking everywhere is so fun as around every corner is something new and exciting. Hope to get back soon!

    • Emily July 2, 2017 at 3:04 pm

      That is handy having friends to stay with – lucky you! The hotels can get pretty pricey, especially during peak season. I don’t think I’ll ever love anywhere as much as I love Key West!

  • Harmony at Momma To Go July 1, 2017 at 9:32 pm

    I’ve still never been to key west. I’m in naples a lot, and there is a ferry over I’d love to take! These are great tips I didn’t realize key west was so big!

    • Emily July 2, 2017 at 3:03 pm

      It is quite big, and crammed full of hotels and bars! Despite the hustle and bustle it is beautiful, and I cannot recommend it enough.

  • Aurelia Teslaru July 2, 2017 at 4:47 am

    Never been here but I would definitely want to go! This place looks amazing and your recommendations are on point!

    • Emily July 2, 2017 at 3:02 pm

      Thanks Aurelia! You should definitely visit one day