Tips for Selecting a Hawaii Vacation Rental

Pool at Hali'i Kai vacation resort on Hawaii, the Big Island
Pool at Hali’i Kai vacation resort on Hawaii, the Big Island

As I’ve previously mentioned, renting a vacation condo/villa is a great way to save money on your Hawaii accommodations. The only issue is that there’s not a perfect rental site that covers all the islands.

When I start to look for a vacation rental, I tend to gravitate to because it has the largest inventory of Hawaii vacation rentals from all islands, plus I get to choose the exact unit I’ll be renting. I like having that kind of control. is another good source, particularly for solo travelers and couples, though they also have some accommodations for more people.

As you search for a Hawaii vacation rental, how can you make sure you’re not getting a dud? Sadly, there are scammers who are looking to take advantage of tourists. So, what can you do to protect yourself as you use VRBO or any other vacation rental company? Here are six tips that should help.

1.  Pictures are worth a thousand words.
Don’t waste your time considering any rental that only offers a minimal number of photos. Virtual video tours are a definite plus. When I look for a rental, I want to see these photos:

  • Views of and from the lanai (balcony) and not just one cleverly angled photo that’s zoomed in a bazillion times to make a far away condo look like it’s oceanfront.
  • Multiple kitchen photos
  • Multiple photos of all bedrooms
  • Multiple photos of all baths
  • Multiple photos of the living area
  • Photos of the shared amenities, such as pool, tennis courts, hot tub, etc.

Do the photos indicate that the unit is well kept? Don’t be shy about asking the owners to email you additional photos.

2.  Talk to or email with the owners.
Ask them as many questions as you can think of. You need to be comfortable that these people really do own the place, that they’ve honestly described their rental, and that they’ll take care of any problem that pops up. Politely ask the owners to provide proof of their ownership such as a link to online tax documents. Ask them what their procedure is for getting a key. Ask them what they will do to respond to any issues that might pop up with their rental during your stay – for example, what would happen if the refrigerator didn’t work. Ask them where the nearest grocery store is. Politely ask, ask, ask until you’re comfortable with the owners.

3.  Pay with protection.
On the last rental we chose from VRBO, we paid by credit card on PayPal. That’s probably the safest possible way to pay because only PayPal has access to your credit card number, plus if a dispute arises, PayPal will act as the intermediary. Your credit card company may also offer you a level of protection. Please note that you do not have to have a PayPal account in order to pay via PayPal with your credit card.

On this same note, if an owner asks you to wire money to them, I recommend you move on to another property. That is a common practice of phishing scams. (For an example of phishing scams, see this link.)

4. Search for reviews.
Fortunately, vacation rental reviews have become more readily available in recent years. I’ve noticed that TripAdvisor has lots of vacation rental reviews. To find rental reviews, google the name of the condo resort along with the unit number or address.

5.  Check around for pricing to make sure you’re paying a fair rate.
If you google the name of the resort complex, you’ll find other sources for renting in that area. From that you’ll be able to compare pricing.

6. Negotiate.
We are not hard core wheelers n’dealers, but I don’t think we’ve ever paid what the owners asked. It never hurts to ask for a better price, especially if you are staying longer than a week.

Since we originally published this article, we’ve written another article with even more tips for selecting a Hawaii vacation condo.

  1. We stayed in a hotel the first trip without kids. The second trip ( with kids) we stayed in some bungalows right on the beach, they had a kitchen etc. The third trip ( with kids) we stayed in a rental house. With kids I think a kitchen is an absolute must for us! I really like the privacy and uncrowdedness of a condo or house.

  2. Excellent article, Sheila! I have started googling the address of condos/houses I am considering for rental to make sure they aren’t in foreclosure or a short sale. With the issues in the housing market I don’t want to put down a deposit on a place that may not be available when I get to the Islands.

  3. Attention Hawaii Vacation Rental Owner/Companies —

    Please do not leave fake reviews. Your comments will not be approved.

  4. I’ve used vrbo three times now for private homes with great success. I recommend it to everyone!

  5. Great tips.
    I suggest that if you do rent a really good place that you post review for the property on HomeAway/VRBO and Trip Advisor. Yes, there are rental management companies who post bogus reviews, but if enough genuine people provide feedback either good and bad it helps. Services like Trip Advisor provide a blind message service, so you can contact the reviewer to ask follow up questions.

  6. Hi Sheila, my girlfriend and I are looking at travelling to Hawaii for about 10 days with our partners, next year around April/May and the 4 of us were wanting to stay in a private villa/ beach front house, we dont want to pay the high prices of the hotels either. Do you have any recommendations? Even suggestions about not staying on the mainland? This is our first trip to Hawaii. Thank you 🙂

  7. HI Sheila, my wife and I are planning on a trip to Molokai. We have narrowed our search down to two places to stay and I just wanted to see if you or anyone has stayed at these areas. The first one is at the Paniolo Hale condo complex and the other is at Wavecrest in Kaunakakai. Any thoughts on these would be so great.
    P.S. Thanks for all the articles it really helps!

    1. Hi Don – thanks for reading Go Visit Hawaii.

      I haven’t stayed at either condo complex so I can’t say for certain what the experience is like. I tell you that so that you take my opinion with a grain of salt. 🙂 If I were deciding between the two, I’d choose Wavecrest because of it’s central location and proximity to the island’s restaurants.

      At one time, Paniolo Hale was probably a very nice and well kept resort. When we drove by it in June, it seemed a bit deserted. I do recommend that you drive out that way to check out the beaches in that area and/or catch a sunset. Just make sure that the conditions are safe before getting into the water.

  8. The next time I go to Hawaii, I will for sure go with a rental as opposed to a normal hotel. As you listed here, pictures are worth a thousand words as a good rental would have a wide variety of pictures to where you can really see what you’ll be getting into. That and I would talk to the owners as it would be a good way to see about the availability and how they go about doing business.

  9. Hi Sheila,

    We are planning a trip for 10 to Maui or Oahu in November. I have been searching several sites for a 5 bdrm home/villa with a pool and hopefully oceanfront. Very hard to find. My husband and I have visited Maui on several occasions and have stayed at the Grand Wailea and the Four Seasons but with 9 adults and a toddler we now need different accommodations. Any suggestions?


    1. Assuming you’ve already looked through VRBO, FlipKey and HomeAway?

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