Tips for Booking a Vacation Rental

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I am so excited to write my first travel related post here on Momma To Go. I anticipate that is what I will mainly focus on (with fitness and parenting being a close second), but over the last week I have been trying to get out seasonal content (Halloween costumes #1 and #2) and had both kids sick, so I am only just writing this now!

I have so many important travel stories and great tips and tricks I want to share with you all. But I need to start with an article that will help you not only get the most out of your trip, but save you a ton of money as well.

If you read my first post, you know that my family traveled to the state of Hawaii for three weeks this past summer. One of the ways we were able to afford to stay so long, was to rent condos for the majority of our stay. We did stay the last 5 nights at a resort, but the other 2 and a half weeks we stayed at three different rental homes.

There are definitely pros and cons to rentals (vs. a hotel). I will go deeper into that in a later post, but the pros for this trip were to have more space, to be able to cook some of our own food (important in a place like Hawaii where EVERYTHING is priced at a premium) and to be able to do laundry. You can’t go three weeks without doing laundry!

In the past, when traveling with my awesome group of girlfriends (I tend to refer to them as #thegirlfriends) I have stayed in rental apartments and houses. But I was never the one to actually book the accommodations, just happy to write a check for my share. So with this trip, I was a little nervous about finding a place over the Internet and forking over a chunk of money without having the security of a hotel name attached. What if we showed up and it was like a John Candy/Summer Rental situation? P.S. I love that movie!

Friends seem to recommend and trust sites like Vacation Rental By Owner (VRBO) and Airbnb, so that is where I began. However, I quickly realized there are so many properties for rent and I was very overwhelmed. I literally didn’t know where to start! So I went to my trusted friend, Google and searched “tips for booking a vacation rental”.

And surprisingly there was not much information!

I was on my own. So after doing a ton of research, ultimately booking three different vacation rentals in Hawaii, and having come out, happily, on the other end, I am so pleased to share my tips for booking a vacation rental.

Tips for booking vacation rentals (VRBO, Airbnb, etc.) employing one of these tips saved me $80 in Maui!

Tips for Booking a Vacation Rental

Start with a list of non-negotiable amenities. Since we had recently stayed at a family member’s Florida condo, we had an idea of what we could, and could not, live without. I easily put together the list of must haves:

  • Wi-Fi (in the Florida condo there was no Wi-Fi and we spent an obscene amount of money buying data from AT& T)
  • Bathtub (my kids hate showers, again for one or two nights that would be fine, but not for 7 or 8 days)
  • Air conditioning (not all places in Hawaii have AC)
  • Washer and dryer
  • Pool on site
  • Parking

The rest was gravy. I mean some units had Netflix- awesome, some had a second bathroom – nice, some had stainless steel appliance – modern, but not a deal breaker.

I literally kept the list in front of me so when perusing the long descriptions of the properties I could check off the features. You look at so many listings they start to blend together. It was helpful to have this list right there.



Narrow down search area first. The first island we visited was Maui. I started chronologically and went onto VRBO and figured I’d find a nice 1 or 2 bedroom condo to rent. But I quickly discovered that Maui is actually a decent sized island, with distinct areas. I had to first figure out what part of the island we wanted to stay at so I could narrow the search!

Tips for Booking Vacation Rentals (VRBO, Airbnb, etc.) one tip saved me $80 in Maui!
There are over 7000 units for rent in Maui on VRBO! Need to narrow it down! I recommend Kihei area.

So that took some research. I read blogs and consulted my Fodor’s Hawaii. I read the descriptions of the areas, looked obsessively at maps and tried to ascertain what would be the most convenient, fun and not super expensive place to be. I narrowed it down to  Kihei and Wailea and thus was ready to begin my accommodations search..

So unless you have a very specific destination in mind, or something you want to be close to (for example, being close to Disney on an Orlando trip) you need to first figure out your preferred location to narrow your search.


Look at the pictures. This one might seem obvious, but pour over the

tips for booking vacation rentals (vrbo, airbnb, etc) one tip saved me $80 in Maui!
View from lanai, Maui Kamaole H-111, Maui, Hawaii

pictures and read every detail in the property description. If a property did not have good pictures, or any pictures, I skipped over and kept going. When looking at photos of one specific room or space, I tried to envision how the entire unit was set up. To get a feel for the flow and size.

Sometimes pictures can distort and make you think something is larger than it really is. Look closely to get a sense of how well the unit is maintained (and the grounds if they have photos of the pool or clubhouse).

Look at the reviews. I’m a skeptic. I look at good reviews with a grain of salt (I mean did the owner get his best friend to write this?). As with any review-oriented site (Trip Advisor, Yelp, etc.) I look for patterns and consistencies in the glowing comments, and I also read the negative reviews closely. For the area I was searching there was so much inventory that if a unit had a bad review, even one, I just moved on.

Tips for Booking a vacation rental (VRBO, Airbnb, etc). one tip saved me $80!Don’t look at the Cost Per Night. For me, when searching on VRBO especially, it was hard to always compare units using the average cost per night. Each one had different fees (cleaning, processing, some refundable, some not) so if I liked a property; I just clicked through on GET AN INSTANT QUOTE and looked at the total for my dates to get a more accurate comparison.



Book directly – if possible. This is a tip that saved me $80 on my Maui stay. If the unit you are interested in is being offered through an agency, go ahead and book directly through the agency itself. In Maui, I got the same unit, for the same price by booking directly through Rentals Maui and saving the $80 VRBO fee that I would have paid when you book through that site (it seems the renter is not always assessed this fee, varies by property). Now in Kona, I was booking a unit owned by a gentleman who lives in Michigan and just rents out his townhouse when he is not using it, so that was not an option. For that property I booked through VRBO.

Tips for Booking Vacation Rentals (VRBO, airbnb, etc) one tip saved me $80 in Maui!

In the end, we were very happy with all of our rentals. After a lot of work (worth it in my opinion) we ended up staying at these three properties in Hawaii:

Maui Kamaole H-111 for 7 nights (on the island of Maui in the town of South Kihei). This was a one bed, 2 bath condo.

Mack’s Shack for 1 night (on the island of Maui in the town of Hana) I also booked this directly through the owner but originally found it on Airbnb. This is a free standing plantation home on the remote part of the island (Road to Hana post coming soon!). It was a one bed, one bath, that slept four.

Kona for 8 nights (on the Big Island in the Keauhou Resort area in the town of Kona). This was a 2 bed, 2 bath townhome.

To me, staying in a vacation rental means having a bigger space, some separation from the kids, and significant savings and convenience from having a kitchen. I think its a great way to enjoy your vacation and live like a local. You need to do the legwork to find the property that is right for you, but its so worth it!

What are your best tips for booking a vacation rental? Please, please, share in the comments!



Check out Epidsode 130 of Epic Education Podcast where Jason gives AMAZING tips for booking an AirBnB!


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Vacation Rental Booking Tips. Best tips to get you a cheap and wonderful vacation rental. #travel #traveltips

Other awesome Hawaii posts:

Maui Must-Do Activities

Road to Hana Tips and Itinerary

Best Big Island Beaches

Hawaii Money Saving Tips


please share:


  1. This was really helpful! Traveling with a 4-year old and a baby, we love the space of renting a whole property, but it is scary to book in the beginning! I have heard great things about VRBO and Air BNB, you might have just give me the push to give them a try!

  2. I love your idea about writing down your non-negotiable items. So smart. There are a few things that we definitely want to have on-site when renting on vacation. Pinned!!

  3. Love your tips! We use HomeAway, VRBO and Airbnb a ton since we are a family of 7. We’ve only had positive experiences and that is mainly because I too pour over the details, study the pictures and read the reviews. And agree that you always have to check to see if you can book the property directly to avoid the VRBO or HomeAway fees. Smart!


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