Travel Brainstorm

Key West Getaways for $66

Key West Getaways

Key West Sunset from Mallory Square

Enjoy Affordable Key West Getaways

by Jon Mohatt, aka Travel Brainstorm

As I mentioned in my last post I am in the process of retiring from the Air Force, so to celebrate, my wife Courtney and I wanted to spend a few days away, preferably in a place we’ve never been and near or on the ocean.  With three daughters, trips alone are few and far between so wanted to make sure this one was special.  We also wanted to ensure, as always, that we had great accommodations without breaking the bank.  Therefore, I turned to reward points to see what I could conjure up.  I remembered reading an article on Million Mile Secrets (MMS) web site about a trip Emily and Daraius took to Key West.  Courtney and I had never been to Key West, and it is certainly near the ocean, so we felt it was a great choice.

Flight Planning

As I have said before, if you are going to use points to elevate your travel experience on a budget, you need to plan well in advance.  At the time of this trip our home airport was IAD (Dulles) in northern Virginia.  Many airlines, to include Southwest Airlines, fly in and out of IAD so I knew having a Southwest Companion Pass would be a great way to go for our airline tickets as Southwest Airlines also flies out of Key West.  Following the advice of Daraius from MMS, I started working on acquiring the points necessary to gain my Southwest Companion Pass.  I began this quest in late 2013 so that it would be activated as early as possible in 2014, making it valid through the end of 2015.  This process will be detailed in a future post (Link).  Long story short, I was successful and had a valid companion pass in hand by February ’14.   I was anxious to put it to good use so Courtney (my “Companion” and wife) could fly free to Key West with me.  It was worth the effort and worked like a charm.  We decided to fly into Ft. Lauderdale so we could drive out to Key West and stop in Key Largo on the way to experience all the scenery.  It too, worked out great and we’re glad we did it but were happy to be flying directly out of Key West on the way home.

Southwest and Key West

Our Southwest Companion Pass really made this trip possible for such a low price

Hotel Accommodations

On our drive out to Key West from the Fort Lauderdale airport we picked Key Largo to stop and visit and spend the night.  Since I had acquired Platinum status with IHG Rewards Club I looked for IHG hotels in the area.  I found a Holiday Inn resort right in Key Largo on the marina with good reviews so I reserved a room.  With Platinum status I was hopeful for an upgraded room and that is exactly what happened.  Upon check-in we were upgraded to a deluxe room with marina view.  All worked out as planned and our trip was off to a great start.

When looking for a room in Key West the first thought was to find a hotel with a nice beach area.  Having never been to Key West we didn’t immediately realize that Key West has very little beach front.  After reviewing the accommodations available (on TripAdvisor of course) and researching where folks liked to stay it became apparent that finding a hotel on a beach in a desirable location in Key West was next to impossible.  Many of the hotels that do have beaches really only have small man-made beach areas so we decided location was more important than having a place to sit on a beach because that is not really why people go to Key West.  People go to get out on the water!

After looking at all the choices we decided we wanted to stay at the Hyatt Key West Resort and Spa or The Westin Key West Resort & Marina.  We were only in Key West for a total of two nights and wanted to make sure we spoiled ourselves and knew we couldn’t go wrong with either choice.  Since I didn’t have enough Hyatt points for the two nights and didn’t want to transfer Ultimate Reward points to my Hyatt account, we went with the Westin.  We also liked the Westin’s location better than the Hyatt’s because it is right on Mallory Square which is the perfect spot to base out of if you want to be in the middle of it all and watch the beautiful sunsets from your room right on Mallory Square. Since we were going to celebrate, we definitely wanted to be in the middle of it all!

Our balcony sunset views were a special treat

Our balcony sunset views were a special treat

Rental Car

Since we were flying into Ft Lauderdale we were going to need a rental car to get to Key West.  I figured that if we were going to do the drive we should get the most out of it, and what better way to do that than with the rag-top down?  I did the usual check of the Budget, Alamo, Enterprise, Expedia, Travelocity, Orbitz, Hotwire, Chase Ultimate Rewards and Citi Thank You travel portals for the lowest rates but settled upon the Costco Travel site to book as they provided one of the lowest cash rates for a convertible and allowed me to save my Chase and Citi points for better redemption opportunities.  I also knew that if I used my Barclays Arrival credit card to charge the car I could pay my bill using Arrival points once it hit my credit card statement.  Always be sure to check several sources to compare when booking travel with cash or points to ensure the best deal.

Key West getaways are more fun in a convertable

Key West getaways are more fun in a convertible

Trip Expense Summary

Here is a breakdown of the trip’s total travel cost and analysis of our savings through the use of loyalty and reward points.

Travel Expenses Cost What we paid Savings
Southwest Airline Flights $593.50 X 2=$1,187$10.00 (Fees) 35,610 Southwest Pts.$10.00 $1,187
Westin Hotel (Key West) Ocean View Deluxe Room $1,392.26 (2 Nights) 40,000 SPG Pts.
$56.26 Resort Fees
Holiday Inn (Key Largo)Marina View Room $336.38 (1 night) 35,000 IHG Pts. $336.38
Alamo Rental Car $142.40 12,816 BarclayCard Arrival Pts. $142.40
Totals: $3,068.04 123,426 Points
$66.26 Cash


There were a few key events that made this trip possible for only $66.26 in travel expenses.  One was the acquisition of the Southwest Airlines Companion Pass that allows your companion to fly with you for free on any Southwest flight.  The second was having points acquired and saved in multiple loyalty programs so we could take advantage of the hotels and services that were available in the locations we visited.  The beauty of the BarclayCard Arrival and Chase Ultimate Reward points is that they can be used for most brands but sometimes having points in the system you want to use, like in the case of Starwood Preferred Guest program, is the most point efficient way to get what you want.  I like to be efficient with my point utilization to stretch my points as far as possible.  With this trip we were able to save over $3000.00 by using points, thus making a budget busting trip well within our travel budget.

Key Lime Pie at Kermit's

Key Lime Pie at Kermit’s

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I don’t think you are allowed to go to Key West without getting this photo?

As always, happy brainstorming and safe travels!  Be sure to sign up to be notified of future blogs posts (top of right sidebar), let your friends know about this blog and please “Like” the Travel Brainstorm Facebook page!

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9 thoughts on “Key West Getaways for $66

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  3. Rachel Johnson

    Quick questions that I am struggling with…. I am a small business travel planner. I probably book $3000 in airfare per month, but it is all booked on my various clients cards. If I book their travel through the Ultimate Rewards portal on Chase, but I am not using my card do I still earn Ultimate Reward points? I have never done this, but am now wondering if it is a missed opportunity for me. Thanks!

    1. Jon Post author

      Rachel, so sorry for not getting back with you sooner but I really don’t have much experience with being a travel planner for business travel for others. I’ve always booked my own travel, but I do know that some travel portals will grant the points and/or rewards to the one making the bookings. I suggest you contact some other travel planners to see what they are doing for loyalty program accumulation. In the end the points or miles normally go to those doing the flying and having the charges placed on their cards, sorry.

    2. Diane

      I have booked hotel rooms for my husbands company thru the Ultimate Rewards portal (thru and earned ultimate reward points for them. In my case, I logged in to my Ultimate Rewards portal, then selected (4x points) and made my hotel reservations. I would get an email in about 10 days that I had earned Chase bonus points. I did not have to use a Chase card for the transaction or even my credit card. I used my husband’s business credit card.

    3. Jon Post author

      Diane makes an excellent point, thanks Diane! One could also use the same method to book using a cash back site such at and earn a cash rebate if they prefer that over points. I just checked and noticed Marriott was paying 3% and was offering up to 7%.

      1. Rachel Johnson

        Thanks for your replys. I am definitely going to try. I also have been using Expedia for the last year, and just recently discovered that Orbitz pays much better rewards, I may be changing my booking engine of choice, plus trying to capitalize on points as much as possible.

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