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Pros and Cons About Booking a Vacation With Points

Beaches in South Kauai

Poipu Beach

I’m sure you are all sick of hearing about my Hawaii vacation by now, but it really was the highlight of the year for us so far. It also took more than a year of planning to book most of the trip with points and miles for our family of three. We’ve booked smaller, closer trips with points before, but this was the first time we’ve really used our credit card rewards for high end resort stays and expensive flights. Let me say that this is in no way a negative post. Taking a two week vacation is something I used to only dream about, but now that I know the ropes, I think we can do even longer periods of travel in the future. However, there really is no such thing as a free lunch, so here are the pros and CONS of booking a vacation with points.

Cons of Traveling With Points

Again, I am not being negative. Maybe these should be called reminders instead of cons?

Award Rooms Are Small

When you book a standard award with points, it usually isn’t for the nicest room in the place. If you’re like me, you probably don’t have hotel status unless it automatically comes with a credit card you have in your wallet. I’m never going to stay anywhere enough nights to be a “valued guest.” Award rooms might be on the floor with no view or in the least desirable part of the hotel. They also might be small, with two double beds or one king. In non-US locations, they might even have twin beds.

award room with Hyatt points

Rollaway beds were free at the Grand Hyatt

This might be fine for a single or couple, but if you are traveling with kids, putting 4 or 5 people in a room with a one bed could be a challenge. Personally, I could care less about a view or what floor we are on. If we have a view, great. If not, I didn’t come on vacation to see the sights from my bed.

We will sometimes use extra points or pay an upgrade fee to have a bigger room with a pull out couch or rollaway bed. If we are staying briefly, it’s no big deal, but I know our time in Hawaii was much better because we had some extra space. It’s all in what you value, but just be prepared that your room with points might not be the one featured on the website.

Watch Out For The Extra Fees

Many people think travel with points is free, but with flights, you still have taxes and sometimes fees to pay. With our tickets on Hawaiian Airlines, we only had to pay $10 for each reward ticket, which is a smokin’ deal. Some international airlines tack on fuel surcharges that can be hundreds or even thousands of dollars on a business or first class tickets. Make sure to check the airline you want to fly before planning which points you’ll need to book.

With hotels, when you book a higher end place on points, there won’t be taxes, but some might still make you pay daily resort fees or parking charges. Even if there are no fees, it might be valet only or you might have to use a bellman to carry around your luggage. I guess you could not tip, but that’s pretty rude. All in all, if you pick options with self parking and try to avoid unnecessary services, you should come out ahead, but if your “free” room costs $100 a day in fees and tips, you might have been better off booking a less fancy place, at least from a financial stand point.

Beaches in Kauai with water spouts

Spouting Horn. No crowds right before sunset!

Vacation Lifestyle Inflation

I never stayed anywhere nicer than a Ramada or Holiday Inn growing up. Motel 6 used to be my lodging of choice when I was single. Now that I’ve been in a few nice hotels and resorts, my tastes have gone up. Not having groups of motorcycle gangs in the parking lot or weird stains on the carpet is not really a bad thing, but it’s easy to get caught up in vacation lifestyle inflation.

The Grand Hyatt in Kauai really is all that and a bag of chips, but you will pay lots for that extra bag of chips.  Standard rooms go for $700 a night. The room we had books for $1200/night. People who actually pay these rates are either really stupid rich and don’t need to worry or they can’t afford it and are living beyond their means. Regardless, you will feel special if you stay here or somewhere similar. I don’t know how many times Jim and I looked at each other and felt like we had “moved on up” like George and Weezie.

Staying for a reduced rate might make you feel like it’s OK to eat the $31 continental breakfast (yes, actual price!) or pay $150 a day to rent a cabana so you can sit by the pool under a tent. We did spend some money on this trip, but it was pretty much planned ahead of time. Make sure not to get sucked into a $19 room service hamburger if that isn’t what you wanted to spend your vacation money on.

Pros of Traveling With Points

Monk seal in the wild

Rare Monk seal sighting!

Duh, It’s Cheap or Free!

There is no way on earth we would have gotten to stay in some of the places we stayed on this trip if we hadn’t booked with points. If you’ve never stayed in a nice hotel, it’s a wonderful experience and one I highly recommend.

If we had to pay out of pocket for this trip, even staying in a cheaper place would have been a few thousand dollars. I won’t say it would have stopped us, but it would mean we could only go on vacation every few years instead of taking  some sort of trip every month or two.

So far this year, we’ve been to visit family in Kentucky twice, to Phoenix, San Diego, Aspen, Moab, and now Las Vegas and Hawaii. We’ll also be heading to Yellowstone National Park this fall and back to Phoenix and Moab later in the year. I realize most of these are not expensive trips, and we don’t use points on all of them.

By using our points for the bigger trips, we are able to take several smaller ones throughout the year. If that isn’t reason enough to pay off your debts and get your financial life in order, I don’t know what is. I didn’t get to see much of the world growing up. I think I still turned out OK, but I know travel makes me a happier person, and life is just too short not to be happy!

About Kim Parr

Kim Parr is a private practice optometrist, freelance writer, and personal financial blogger. You can follow her journey to 20/20 financial vision at Eyes on the Dollar.


  1. I can definitely see how my vacation expectations have risen – and I haven’t even booked with points yet! That’s probably the main reason why we haven’t gone on vacation in a little while :-). But really, vacation inflation is just like lifestyle inflation. Once your standard goes up, it’s crazy hard to get it to go back down!

  2. Sounds like a great trip Kim. I’d like to add one potential con to the list. I believe for some people the “lure of getting reward points” causes them to overspend in the present. In other words, it becomes a justification for spending…”It’s OK to spend on this because I’m getting points.” If that is the case, then the trip is costing them more than they realize.

  3. George and Weezie – funny. 🙂 Wow – I heard that Hawaii was expensive, but man, $31 for a continental breakfast? OUCH! Thanks for sharing, Kim. As for me, I never get tired of hearing about your Hawaii vacation. 🙂

    • Thanks Laurie. There were some good deals on food that we took advantage of, but for the most part, you do pay a high price to live in paradise.

  4. From the pics I saw on FB, it looked like a great trip! I hear you on the vacation lifestyle inflation. We’ve been on a couple of rewards trips and when we have to book on our own we want the nicer hotel. But, I guess that just means more churning to get the nicer spots. 😉

    • I think there has to be a limit at some point, but as long as we aren’t crazy with our applications, it’s a fun and really rewarding hobby.

  5. Wow $1,200 a night is crazy! We’ve always wanted to stay at that hotel, so it sounds like we have to start churning a little more 🙂

  6. Glad you had an awesome trip Kim! Hawaii is on the list for us and we are planning on doing it with rewards. I got the taste when I paid for the FinCon trip almost in full with rewards, so I am excited about what I can do with some more practice.

  7. The price of incidentals at those places is vomit inducing. $31 for breakfast? What exactly are they serving? That’s one of the reasons I seriously enjoyed my all inclusive. 5 days with airfare for less than one night at a fancy hotel with a zillion incidentals. Though I wouldn’t mind getting it for free 😉

    • I didn’t ever check it out, but there is no way I’m paying $100 for us to eat breakfast. Even if it was filet mignon, no way. My daughter would only want a muffin or cereal anyway.

  8. I agree with Michelle that 1200 is…wow!!! I think it kind of comes down to a balance. It’s nice to do that luxury thing every once in a great while, but do the small, crappier once for quickie trips, solo trips..not something where the point of why you are staying is complete relaxation. Sounds like a great time! Loved the pics on FB too.

    • My Mom was so freaked out about all the plane incidents recently that if I didn’t post pics every day, she was convinced we were in mortal danger. I like luxury trips, but also enjoy camping and cheap road trips, so I do think a good balance is the way to go.

  9. That’s a great point about the rewards rooms being smaller than rooms you would book directly. We have grown accustomed to the small room experience, but some people may be surprised. It is also crazy how many extras the hotel can get you for like the food other costs. It makes sense to look at the hotel menu pricing before you go and make alternative plans if the hotel costs will break the budget. We typically travel with breakfast bars or grab food offsite as much as possible.

    • We stopped at Kmart right after the airport to stock up on snacks and breakfast items. There is no way I’m paying for breakfast. My family doesn’t eat that much in the morning anyway.

  10. Travel is an excellent option to use reward points. I’ve used them to help buy probably $1500 worth of tickets in 2 years.

  11. Great point about the reading the fine print on all the “extras”. Because one way or another you will get hit with a few, so like you said you want to make sure you budget for those expenses too. $1200 for a room is crazy, but I would sure would like to stay in a $1200 room … on someone else’s credit card! LOL! I can’t image … are all the faucets pure gold? 🙂 I’m glad you guys had a great time in Hawaii!

    • The faucets were not gold but the toilet did have a heated seat and a bidet option of front wash, back wash, or both at the same time! I’m sure it might be nice in a cold climate but every time I sat down, I felt like someone had just gotten up and left it all warm.

  12. Getting sucked in to justifying purchases due to saving elsewhere is TOTALLY something that I would do and have done. These are all awesome points. Nice work using a rollaway bed, I never hear about those anymore!

    • It was actually a really nice bed. I seem to remember something like an army cot when I was a kid and stayed in a motel room with my grandparents!

  13. It’s a little different than booking a trip with points, but we are staying at a very nice resort on Wakiki beach from the giveaway we won. I’m a bit worried about vacation lifestyle inflation. When we go I will already have paid the taxes, so it will feel like a true “freeroll” and might make me want to spend more on food, drinks, etc.

    • I hope you get to have your drink of choice on the beach. I normally do not drink, but there is just something about having a fruity cocktail at lunch on a warm day.

  14. Thanks for presenting the ‘cons’ side to travel hacking! It’s a much needed perspective. Reasonable expectations make for a better experience.

  15. I’ve stayed at very nice hotels that I would never pay for (700 a night room in Hong Kong). I value my points at 2 to 3 cents if I don’t get that value I don’t redeem. Looks like your family had a great time here, I often take for granted what people spend thousands to enjoy

  16. Glad you had fun, Kim! Vacation inflation is the worst part about traveling with points. My expectations are infinitely higher now that I stay at nicer places I would never spend real money on.

  17. Awesome post, I do love the moving on up feeling, and I’ve got to say, my vacation lifestyle has inflated a bit. Kind of funny when you think I pay much less overall for vacations now…because of points!

  18. Great wrap up. I am going to be posting about my ‘free’ vacation soon. It’s nice to be able to just go and not have to worry about when and where you can use points. I do not go on vacation nearly as often as you, so I do not save as much.

    I am splurging a bit on this vacation, but I am going during the off-season to make up for it.

  19. Kauai! We were there 2 years ago. We went on Air Canada points but shared a time share 2 bedroom condo with my BIL/SIL We were there for a family wedding. My first time to Hawaii. We drove all around the Island a few times. It was really nice there on the North shore.

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