Somewhere between a little grass shack in Kealakekua and the penthouse suite in the Hilton lies the condo—a place to call your own that has all the luxury of a resort. Condos will appeal most to active visitors who get out and explore during the day and want a comfortable place to come home to at night. Here are some tips to get a good deal on condo, and not wind up with a lemon.
1. Book way in advance and negotiate with the owner, using websites like VRBO and Home Away.
2. Book in a "shoulder season" like spring and fall, when demand is low.
3. Buy in bulk: The longer you stay, the lower the price you will be able to negotiate. Perhaps you can share a month with someone else, or think big and stay for a month!
3. Travel with friends and split the cost of a larger unit. Half the cost of a 2 or 3 bedroom will be less than the cost of a one bedroom or studio.
4. Ask the right questions. Is this a top floor or end unit (more desirable)? How new are the furnishings (Hawaii is tropical, and mold and mildew smells exists is some older buildings)? Is is quiet? How close is the beach (or other features)? Most owners will gladly answer questions. An owner who is not forthcoming is a red flag for a unit that has shortcomings.
5. Spend a little more for a nice condo and then save money by eating in and not going to restaurants.
Of course, each island will have really nice condos, as well as some that suck. To find the nice ones, start by selecting the best regions:
On Kauai, Princeville on the north shore and Wailua on the east shore near Kapa'a are desirable locales. Poipu Beach is sunny (and therefore arid) with lots of choices. Give Suite Paradis a look for Poipu.
On Oahu, Waikiki is where most people stay; avoid Kuhio Avenue (unless you want noise and kind of tacky nightlife) and stay beachfront—or select a unit on the more residential backside of Waikiki along the Ala Wai Canal.
On Maui, sunny Kihei is good for families and couples who want to log beach time near restaurants and shopping. (Kihei has become better by comparison to Kahala, north of Lahaina, which has been overdeveloped.)
On the Big Island, most of the condos are on Ali'i Drive in Kona and Keahou—where traffic can be a hassle and beaches are few. Try South Kohala, where the last decade has seen the construction of beach villas at the backshore of destination resorts in Waikoloa, Mauna Lani, and Mauna Kea.
Once you have honed in on a desireable region and contacted specific owners, use sites like Yelp and Trip Advisor to see what other visitors have had to say. Use Google Earth to see what the physical address looks like from an aerial perspective.
All the Trailblazer guides have specific listings for condos and vacation rental agents. When planning your vacation, you may also want to download the Kindle edition of No Worries Hawaii, A Vacation Planning Guide for Kauai, Oahu, Maui, and the Big Island.