Don’t Be As Dumb as Daraius When You Book a Car Rental!

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I love miles and points because they save me money and let me have Big Travel with Small Money.  Sometimes that is saving money when I rent a car and sometimes that is flying in coach with my Southwest Companion Pass.

But miles and points can consume you!

A lot of miles and points activities can’t be automated and require you to manually check and re-check.  For example, you have to keep on checking if an award seat opens up, or if a hotel or car rate has decreased, or if your credit card bonus has posted.

Don’t Be As Dumb As Daraius When You Book A Car Rental

We Had a Great Time In Key West…Except When It Came Time to Return the Rental Car!

Unfortunately, we don’t have an unlimited stash of focus and concentration.  And the manual nature of many of these tasks means that you sometimes will make a mistake.

1-Way Car Rental to Key West

Emily and I decided to drive from Fort Lauderdale to Key West after the recent Frequent Flyer University in Tampa.  We’ve (I) always wanted to drive on the Overseas Highway to Key West.

Don’t Be As Dumb As Daraius When You Book A Car Rental

I’ve Always Wanted to Drive On the Over Seas Highway to Key West!

We also wanted to fly back to Austin directly from Key West using our Southwest Companion Pass, so we booked a 1-way car rental from Fort Lauderdale to Key West.

The regular rate for a car rental on a site like Hotwire or Expedia was ~$300 for the 1-way rental.  But I used Costco Travel to book a 1-way car rental for ~$160.

Don’t Be As Dumb As Daraius When You Book A Car Rental

I Should Have Stopped Once I Got A Price I Was Comfortable Paying!

Check out the Cheap Car Rental series for the best tips on how to book a car rental!

Be Careful When you Re-Book!

~$160 was a pretty good rate for a 4 day 1-way car rental.

But no!  I had to keep booking and rebooking in the hope of finding a cheaper rate.  Rental car prices often decrease as you get closer to the time when you pick-up the car (unless the rental car company is sold-out).

I finally found a rate for ~$90 on the day we were supposed to pick up the rental and cancelled my old reservation and re-booked at the cheaper rate.  I even mentioned to Emily how I got the rate down from ~$300!

Fast forward to the airport at Key West.  We had a wonderful time at Key West and I dropped Emily off at the terminal and went to return the car.

I looked for the signs to the Alamo lot.  There were signs to other rental car agencies, but not to Alamo!  So I drove around again thinking that I had missed the sign, but there really was no Alamo lot at the Key West Airport.

So I got out my Costco Travel confirmation and realized that I had booked a round-trip rental and had to return the car to Fort Lauderdale (instead of a 1-way rental with a drop-off in Key West)!

Don’t Be As Dumb As Daraius When You Book A Car Rental

I Didn’t Double-Check the Drop Off Location!


What makes this all the more embarrassing is that I reminded folks who attended our Rental Car Session (co-presented with Rapid Travel Chai) at the Frequent Traveler University that you should stop booking and re-booking once you find a rate with which you’re happy!

Our flight was leaving in 1 hour and I needed to fix this as soon as possible.  So I called Alamo and asked them if I can return the car to their off airport location in town.  They agreed to let me return it to an Enterprise location close to the airport, but I’d have to pay the difference in rental price which they calculated at $250.

This meant that I paid ~$340 for the rental ($90 + $250 difference) which is $40 more than the regular rental rate!  Ouch.  Ouch.  Ouch.

The story ends well (besides ruining my travel budget) in that I drove fast to the Enterprise location, returned the car, paid the difference, and made it back to the airport in the free Enterprise shuttle just in time for our flight.

And Emily being a much better person than I ever will be, didn’t “remind” me of my skills at finding a cheap car return.  I’m so lucky to be with her!

Bottom Line

The lesson for me – and for you – is that it doesn’t always pay to be obsessive about miles and points.  

You don’t have to work every promotion, squeeze every mile out of your award redemptions, maximize every dollar you spend on a credit card, and obsessively check and re-check for lower rental car and hotel rates.

Once you find a rate which you’re willing to pay for a rental car or hotel, and which is much cheaper than what it costs elsewhere, let it be.

And spend your time & energy on more important things.

Oh, and double-check your drop-off and pick up location!

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26 responses to “Don’t Be As Dumb as Daraius When You Book a Car Rental!

  1. Ah, if you had tracked it with AutoSlash like you advised your readers in a previous post, you wouldn’t have had this problem in the first place! 🙂

    I’m heading to Key West over Xmas. Are you planning on doing a blog post on your recent trip? If not, any pointers on stuff to see/do?

  2. Don’t think of it as being ‘dumb’….think of it as a $250 tuition payment toward travel education! (Everyone does stuff like this once, including me.)

  3. Also heading to Key West and doing the same drive. Would love a trip report! Any thoughts on the Hyatt or the Waldorf Astorias there?

  4. I’ve been using for roundtrip car rentals. They keep checking various car rental agencies for lower rates. My FLL rental started out at $285. It gradually headed down in price to $105 all-in for an Avis car rental. No many or cc info is taken until you reach the counter.

  5. There is no National/Alamo station at the airport, it’s in town. And (at least with National) Lauderdale-Key West is not considered a one way, they treat it the same area.

    @Jonathan: My in laws live there, so we go there often. Let’s assume you don’t have kids. I would start with the usual tourist stuff, like Mallory Square sunset, the aquarium (meh..), maybe a conch train tour, Truman Little Whiet House, Lighthouse, Hemingway house, Fort Zachary (very nice beach!), Butterfly museum. (That was in order walking from Mallory Square down South). Have a beer at Sloppy Joe’s and Capt Tony’s. At The Bull you can walk upstairs to the garden of eden and see people running around nude. Might be too cold over xmas though. Catch the band at Rick’s, those guys are fun and entertaining. Have a Key Lime Mojito at Kelly’s for happy hour (was owned by Kelly McGillys from TopGun). Go have a beet at the Porch, one of my favorite places these days.

    Then do a sunset sail and cruise, if the weather is right it’s pretty awesome. One christmas couple years ago we wore our winter coats though. Check out the Stand Up Paddle boarding, that’s pretty cool.

    No idea where you are staying, but check out the Casa Marina (very nice beach) and take the shuttle over to Sunset Key and have brunch at Latitudes. Check out the sunset sitting at Louie’s Backyard.

    Best key lime pie can be bought at Publix (seriously). Good cuban food can be had at El Sibone, cheap but gets crowded after 6pm.

    Ok, enough rambling… Have fun. I hope the weather is warm and nice as it was last christmas.

  6. @Kate: Hyatt is ok, but the location is not great. You will need a cab or other transportation to get into town for the action. Too far to walk.

    The Casa Marina (Waldorf) is our favorite. Two pools, great private beach. You can have dinner on the beach, then lay in the hammocks. You can walk to Duval from there. Daniel and Adrian at the pool are the best, they will take care of you.

  7. Ouch! Thanks for sharing your embarrassing story as a reminder for the rest of us.

  8. $250. That’s like, what, 2 apps?

  9. Kudos to Emily 🙂

  10. My wife’s father drove off the old Key West bridge in an old Stingray Corvette back in the day. His seatbelt wouldn’t unlatch and he had to cut the belt. The throttle stuck and he couldn’t stop. Talk about bad things happening in threes!

  11. Good to know even pros aren’t immune to the most rookie of mistakes! (And thank goodness you have an understanding wife). Considering rental cars require constant checking and rechecking and playing arund with locations and discount codes, I’ve come close to doing that many times. One time I booked a hotel on the wrong date because I had been messing around so much. Thankfully, that particular hotel sent a “looking forward to seeing you” email a few days prior and I was able to cancel in time. Another time I forgot to cancel a Southwest reservation until they sent me that email. That’s when I knew I was juggling too many trips in the air.

  12. I’ve done this as well, but caught the mistake before going as far as you did. One time I even booked a plane to the wrong Springfield, as there is an IL and a MO Springfield. I was on the plane before I figured that one out. That is what makes travel so much fun.

  13. Hey guys-

    I’m going to Vegas in a couple weeks for a conference and will need to book a car rental. I have both the premier and plus Southwest Cards in which I need to meet the minimum spend. What is the best car rental agency to book through with one of these cards? I.e. the best rewards partner with SW?


  14. Great story. And while it does hurt that you had to pay $40 more than your original choice, you should be very thankful that it ONLY cost $40 more. A last minute one way rental could have cost a lot more!

  15. hehehe great story–but its okay bro…humans make mistakes too.

    • @Jonathan @dhammer53 – 🙂

      @Lively @Lisa @Ozaer N. – It still feels silly!

      @Kate – Trip report coming up soon. We stayed at the Hyatt, but the Waldorf was a close 2nd when I was deciding options.

      @Gaurav – I’m a lucky guy!

      @Ken – Good heavens! Good thing he had a knife or something to cut the belt with.

      @Elaine – I might have received some of those reminder emails as well for hotels which saved me from making mistakes!

      @Jeffrey – That’s quite the story!

      @Chance – Depends how long you rent for, but go to the Southwest website and see the different offers for rental cars.

      @scott – That’s very true. In that situation (wife at the airport with our bags checked-in), I would have likely paid more.

  16. Returning Alamo car to Enterprise? Very interesting experience.
    Anyway could you please remind us what credit card has the most car rental coverages in US.
    Thank you.

  17. @kate. The hyatt off front street is one of 2 best located hotels in town. Pier House. Waldorf Astoria is down at the quiet end of Duval Street. Out of the Action. You want to be down at Mallory Square and Front Street area. The other person saying Hyatt is out of the way is talking about other Hyatts near the Airport. Xmas can be cold, usually not. Go during Fantasy Fest for the best party in the US and most popular time in Key West, especially during the finale Capt Morgan parade but hopefully you like nudity and body paint to enjoy. But this is no secret and we are talking highest prices ever.

  18. Beautiful pictures! We would love to be able to cross off the Key West item in our Bucket List someday. Thanks for sharing your story.

  19. @seekingsun – I disagree that the Hyatt is too far to walk. It’s only 1-2 blocks from Duvall Street which is where all the action is. If you’re a Hyatt Diamond, it has the best breakfast I’ve had at a Hyatt. They gave a NTE $116 credit (per day) for breakfast and we were unable to use all of it. There was also one night (I think Wed) where there was a free manager’s reception in the evening with free appetizers and alcohol.

  20. I found shopping for car rentals on Kayak can save you beaucoup bucks at the Ft. Lauderdale airport, I’ll be paying $300 vs $900 the big guys wanted. Just FYI

  21. @jackieb Don’t forget to track your rental for free at We may be able to find you an even better deal!

    • @Tatyana – Short answer is that no credit card will cover you for liability towards others. The United Explorer and a few other cards have primary insurance coverage for damage to the rental car only, but not to other cars.

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  23. I’ve settled on a strategy that gets me a reasonable discount off of list prices, without taking up a huge amount of time.

    I simply scan the prices for the desired car class in Travelocity and Orbitz, then I go to Priceline and make an offer that is 25% to 40% under the list, depending on my perceived chances of scoring a big discount.

    Usually I get 25% off; sometimes even more.

    It’s probably not the optimal way to save on every rental, but like I said, my time has value too.

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