Hawaii House RentalsDuring the 10 years we lived in Boca Raton, Florida, Sam went to Hawaii numerous times on business. Each time, he invited me along. We would pay for the airfare with frequent flier miles and I could fill the other half of his hotel room for free. The only real expense would be food.

But each time I declined. We lived in South Florida, for heaven's sake. Why go to Maui or Oahu when I already lived in the subtropics? I saved my miles for trips to Portugal and Holland (yes, I still call it Holland and always will!) and had wonderful trips with him.

Finally in 2002 — just a few months after moving to Utah — I decided to take up Sam's offer to meet him in the islands. In fact, we decided to take the entire family. And I learned that I had been dead wrong. Hawaii is nothing like Florida. The weather is more glorious, the scenery sublime, and Polynesian people are probably (collectively) the nicest on the planet earth. I have not been to a more amazing spot.

Just a few years later, our family went again. We'd already done the tourist thing in the city. The second time we opted to rent a house — right on the beach — on the North Shore in Oahu. We used  Vacation Rentals by Owner to find our home. Although we didn't ultimately use them due to availability issues, we found our first choice beach house through HomeAway. (HomeAway apparently owns VRBO now, but I don't think they did when we used them.)

Renting a house in an out-of-the-way location has particular advantages, among them:

  • Prices that beat hotels by a mile — especially when you have a big family to house!
  • Kitchen access saves big bucks by allowing cooking and eating at home (although some products, like milk, are still really expensive compared to most of the US)
  • Roomier, more comfortable accommodations
  • Quieter experience with less hustle and bustle
  • Feels more like being a resident than a tourist

There are a few items on the downside to home rental:

  • No maid service
  • No room service
  • Farther from tourist destinations you may want to see
  • Less security

No air conditioning — this obviously isn't a given, but we didn't think to ask about this, the house we rented had none and that made some days (and nights) very uncomfortable

People rent out nice homes for all sorts of reasons. In our case, the owner was a 20-something bachelor who couldn't really afford a Hawaiian beach house. So he rented it out whenever he could (crashing on the couches of (really nice, accommodating) friends) and lived in the home when he couldn't rent it. The rentals helped pay for the mortgage and, eventually, this young guy will have a very valuable piece of property!

Similarly a few years ago we rented a townhouse in Orlando for a quick amusement park jaunt with the kids. The cost savings were similar, and the place was lovely.

If you want a more affordable family vacation — in paradise or anywhere else — look into home rental. It was a great experience for our family with considerable cost savings. We will certainly do it again.