We’ve never stayed in a vacation rental condo before, but I’m kind of interested in renting one for this year’s vacation in Kauai. The prices seem good.
However, I’m aware that pitfalls await the unwary and the inexperienced. Are there any regular condo renters here who can share their wisdom with me?
We’re looking at the Princeville area of the island of Kauai.
I have never had a problem with Prosser Realty. I’ve rented houses and condos from them. Plenty of rentals on the North Shore / Hanalei / Princeville area.
What exactly are you looking to do on your vacation? Princeville is in the rainy side of the island, but it is close to great golf, excellent snorkling, and the Na Pali coast.
However, it’s very far from everything else, including my favorite little town of Kapaa, and it’s a long, long way from Lihue, the main city.
You can find pretty good rentals at the Plantation Hale or several other condos near Coconut Grove, which is more centralized (and near Kapaa).
And, when are you going?
Air conditioning. Ask.
I was thinking Princeville, because I love a warm, humid, jungly climate, and I know that the north side of each island is the more tropical side. I also liked the idea that it was not near any large towns. We saw Waikiki last year and didn’t want to repeat that experience.
However, LargeMarge’s post is starting to make me rethink that. I now know that even the largest town on Kauai is pretty small, so perhaps Kapaa won’t be too urban for us.
We’ll spend a day or two around the pool or the beach, but we’re not really beach people. We instead like to drive around and see jungles, birds, tropical botanical gardens, plantations, people, and little villages. We also like to go out to Japanese and Chinese dinners, and we love plate lunch joints.
As a curious aside, what sort of seasons does Hawaii have? Is there a rainy, dry and hot season (like other tropical places I’ve lived?) I ask because one of Mrs. Shibb’s relatives has a condo there someplace that we can use for free if we want to fly our family out there.
Kauai is a little different from the other Hawaiian islands (at least that I’ve visited - don’t know that much about the big island). It has both one of the wettest spots on earth, and also one of the dryest spots on earth - within only a few miles of each other. There is definitely a “wetter” side (the east coast) and a dryer side (west coast). So Princeville is on the wetter side. The good thing is to keep this disparity in mind - if it’s raining too much, just drive to the other side of the island.
If you’re not into the beach thing as much, then you might do some Menehune artifact seeking as a means to do the kind of things you like to do. The Menehune are these almost mythical people (said to still be living in seclusion in the hills in the heart of the island), and these various structures are attributed to them and were said to have been constructed “over night” (cue Twlight Zone music 
There’s this menehune aquaduct, and the Menehune fish pond (you need to take this kayak tour on a river to see this one. It’s pretty fun, and you’ll get to see the spot where Indiana Jones swung into the river at the opening of “Raiders of the Lost Ark”). I started to get intrigued by these stories, and so I started checking out these various artifacts. Note: the reason these structures are said to have been built over night is because, being smaller in stature, the Menehune were getting their butts kicked by the polynesians that had moved in. So they needed to work at night, covertly to do their thing.
Although it is a bit pricey, I think Kauai is the best island for a helicopter tour. Not only the best way to see the Napali coast, but also you’ll get to see Waimea canyon up close (as in fly right through it).
One other word of warning, unless you have a desire to see what Hawaiian tourism was like in the 50’s, DO NOT waste your time and money on the Fern Grotto. I warn everyone about this.
Also, DO partake in the Lappert’s Kona Coffee ice cream (even if you don’t like coffee ice cream). Kauai is the home of Lappert’s, so they’re all over the place. You won’t regret it.
Have a great trip.
We stayed in a house in Kailua on Oahu. It didn’t have air conditioning, and we never needed it. With Hawaii’s climate, a fan’s all you’d ever need.
-Lil
OK, I have rented condo’s by owner on Maui for a total of approximately 50 weeks in the past 4 years (8 different condos). And I have stayed in numerous bed and bf’s in the past 10 years on all of the islands. You can get a great place or a not so great place and you can’t tell by the pictures.
You have to decide what kind of risk you are willing to take. When we first started renting condos we did it for only the minimum amount of time required (3 to 7 days) so that if it was horrible we weren’t locked in forever. Most of the time we were very happy, or at least satisfied. But for the right price we are reasonably easy to please. $1300 a month for an ocean front condo on maui in the summer that desprately needs remodeling is ok for me. But would probably not be a good deal for someone on their honeymoon.
The more you rent the easier you feel about it. But the first time you send a money order for $1000 sight unseen is pretty tough.
A good place to start is vrbo.com, that’s where we found our first place. Now we know owners and have seen their condos so that makes it easier. But you can get great deals by renting directly by owner.
We have had only one “bad” experience and we have had so many laughs about it that it has become a “memory” rather than a “nightmare” 
I don’t know if this helps but if you have any questions post again, Aloha and Mahalo.
Thanks for all the advice, everyone. It’s really helping me narrow down what we want. One more question: what’s the kid factor at condos? Are they generally rather kid-intensive?
In my experience, if there’s a pool there’ll be some kids. But you also see a lot of retirees.