Back in the day, I had a one-track mind. (No, not THAT track! Although, as a man, I must admit that track does play pretty often.) Every time we’d travel, the first thing I’d do after securing our flights or plotting our route on interstates was book hotel rooms. For years, hotels were all we knew. The brand names grew nicer over time — Motel 6 and Super 8 at first; then La Quinta and Ramada Inn; Hyatt Place and DoubleTree Suites; and, eventually, roomier and comfier boutiques — but always hotels. When the kids were little, this worked very well. They didn’t take up much room, and we needed them close to us. But as they grew, and as those teenage attitudes began to set in, a double bed for the two of them no longer did the trick. (Heck, even a California King is too small for siblings reluctant to share a space.) At the very least, we needed two beds and a hideaway sofa. But, of course, that always bred a feud as well. (“I get the bed.” “Nuh-uh, you got it last time; you take the sofa!”) So, more often than not, we found ourselves with two rooms, at least three beds, and a price tag now double what we had come to expect, with little gain in comfort to show for it.

The Sheraton Waikiki Beach, Honolulu, Hawaii

Enter Hawaii. 2007. My son, then just shy of 13, had qualified for the regional gymnastics championships in Honolulu. My daughter, having just turned 11, was happy to tag along for the ride. As good gymnastics parents do, we booked the nicest room we could in the USAG’s discounted hotel block — upper-floor, with balcony and a decent view, at the Sheraton Waikiki — and set out on our maiden voyage to the Aloha State. The hotel was nice enough, but we learned very quickly that we really didn’t want to spend much time in Honolulu, let alone the über-touristy Waikiki Beach, so we set out each day to discover new, and much more interesting, parts of Oahu. The trip was a raging success — due mostly to Oahu’s beauty and boundless activities — but the one drag day-in, day-out was having to trudge back to a high-rise hotel (as nice as it was) and cram ourselves and our not-so-little tweens into a space built (at best!) for two.

As it turns out, Christine and I would be back in Hawaii — this time Kauai — barely eight months later for a buddy’s wedding. While exploring Oahu earlier in the year, we noticed that the island, outside of Honolulu, was chock full of houses and condos for rent to vacationers. Not wanting to repeat the Hawaii hotel experience in Kauai, we decided to find a condo instead, and we discovered Outrigger.com. Run more like a hotel for purposes of booking and check-in, but with properties that are decidedly condo in construction, Outrigger gives travelers a much more spacious and comfortable lodging experience at only slightly, if any, more cost than a hotel of similar quality. For our destination wedding in Kauai over the New Year holiday, rooms at the Grand Hyatt in Poipu (the host hotel) started (and I mean started!) at more than $400 per night. And that price didn’t buy you a suite, just a standard King room, and one with no view at that. Of course, the Grand Hyatt is a compound of the utmost luxury — high walls and pristine grounds that ensure its guests are in complete isolation from the world outside. Large families with bored, screaming kids might be trapped inside, but that’s just minor annoyance when you’re lying on a freshly combed beach with $15 mai-tai in-hand. Right?

Outrigger Kiahuna Plantation, Kauai, Hawaii

For some people, many of them my friends, that’s a vacation. Not for me. When I travel, I want to experience my destination, all of it, the good and the not-quite-so. I expect my health and safety to remain intact, of course, but in lodging I seek a clean, comfortable place that only thinly veils the grit and the flavor that make my destination worth visiting in the first place. On Kauai, that place was the Outrigger Kiahuna Plantation, a condo complex just steps from the beach and (better yet) from “downtown” Poipu and Brennecke’s Beach Broiler, home of mai-tais that are far too good and too cheap for my liver and my waistline.

At Kiahuna Plantation, Christine and I found a spacious one-bedroom condo with an en-suite kitchen, an enormous living area that gave way to a comfortable patio, and walls full of windows we could cast open to enjoy the sound and the feel of Kauai’s soft winter rains. Kiahuna was our first vacation-rental experience, and for almost a week, it was our little Kauai “home.” The cost to us was $249 a night, during what I’m told is the single most expensive time of year — the week between Christmas and New Years — in Hawaii. We loved everything about that stay in Poipu, and while we have not yet had occasion to go back, we know precisely where we’ll stay when we do.

Since then, the vacation rental has become our norm. Hotels still have a place in our life, to be sure — when it’s just the two of us for a short visit, or when we’re hopping from site to site along the interstate a night or two at a time, or when the culture and personality of the destination dictates, a hotel can be just what the doctor orders. But for much, if not most, of the travel we do these days, vacation rentals are a classic “no brainer,” giving so much more bang — room, comfort, convenience — for the buck that hotels don’t even enter the conversation as we search for places to stay. A few stories to illustrate:

Spring Training, Surprise, Arizona: A life-long baseball fanatic living 15 years in Southern California, I’m ashamed to admit that I have yet to attend a Cactus League game. But a nudge from my parents soon will change that, as we (five of us, including my teenage daughter) will meet up in Surprise, Arizona, for a few days of late-winter baseball. My parents, very much the types drawn to the comfort of the known, were set on a particular hotel … the Holiday Inn Express in Surprise. Fortunately, with minimal convincing, they were swayed to consider a rental property instead: “I bet I can find a three-bedroom house with spacious living area for less money than two rooms at the Holiday Inn Express. Would you go for that?” … “But we want to stay in Surprise!” … “No worries, I’ll only search in Surprise.” … “Deal!”

Spring Baseball! Rental house in Surprise, AZ, Cactus League home of the Texas Rangers.
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And so it was that we found (through www.VRBO.com) this four-bedroom, two-bath house with heated saltwater swimming pool and 55-inch flat-screen TV just four miles from Surprise Stadium. Our grand total (including taxes and cleaning fees) is $265 per night … just $132.50 per family, all-in! My parents were immediately sold, but just for grins, I decided to search rooms at the Holiday Inn Express for the dates of our stay. It was already booked up. For the entire month! Finally, I found a few days with availability three weeks before our visit — before Spring Training even begins. The rate: $159 a night. Plus tax. Per room. More than $330 per night for two cramped rooms. So, not only will we be staying in 1500 square feet of four-bedroom bliss, we’ll be SAVING at least $65 per night between us! As I said above, a “no brainer.”

Lake Wanaka (and the town of Wanaka, right) from several thousand feet
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Wanaka, New Zealand: My family’s “trip of a lifetime” happened this past summer, when we visited New Zealand and Fiji as a final “grand hurrah” before sending the elder kid off to college. We made many stops along the way and enjoyed every single one of them, but the one we most anticipated, by far, was the five-night stay in South Island ski country, in the small but bustling hamlet of Wanaka, situated at the eastern edge of the Southern Alps on beautiful Lake Wanaka. On a tip from the friend of a Kiwi friend, we scoured dozens of listings on BookaBach (www.BookaBach.co.nz; “bach” being the En-Zed term for a vacation property), ultimately choosing a newly constructed, three-bedroom, two-bath gem at 66 Mt. Iron Drive. The house had a beautiful contemporary kitchen (where we cooked breakfast and dinners most days), a spacious living area (where we watched the Lord of the Rings trilogy in its entirety after skiing over the course of three days), and heated tile floors throughout (a very nice touch in the dead of Kiwi winter). The price for all this luxury: $210 per night (US currency), including all taxes and fees.

Our sunrise view before hitting the slopes in Wanaka, New Zealand
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Tipsy croquet at a Central Coast property
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Paso Robles / San Luis Obispo, California: A couple of years ago we did a combined college-tour and wine-tasting trip to the California Central Coast, with four families (13 people total) sharing a four-bedroom, 2.5-bath house in rural Atascadero (found through VRBO.com). After a day of winery-hopping or campus-strolling, we’d cook our own dinners and wind down with a game of croquet or touch football in the spacious yard under the late-afternoon California sun. Split among the four families, this place cost us $135 per night apiece, all-in.

I could go on for hours and hours, pages and pages, talking about the two-bedroom condo just a two-minute walk from the lifts of Snow Summit, or the four-bedroom house shared with three other couples on the slopes of Deer Valley, Utah, or the two-bedroom townhome at the dunes of Pismo Beach, or the five-bedroom ranch house perched atop a hill in California wine country, or …. But I won’t. You get the gist. Thinking, quite literally, outside the run-of-the-mill-hotel box will transform your vacation experience, allowing you to “live” in your destination as though you belong there, as though, for a short period, it’s your very own home.

On your next vacation away from home (and I’ll talk another day about stay-at-home vacations), don’t be content with booking a room. Book the whole house!

~ JD

(Cover photo: My son, Philip, descending Mt. Meru, Tanzania, in the glow of early dawn, with the slopes of Mt. Kilimanjaro looming in the distance.)