Since my first visit to Oahu in 1989, I have stayed in only one hotel on the island- the Kahala Hotel and Resort on the night of my honeymoon. while we have 'ohana (family) on the island, getting a hotel room is generally not the route we take. We've found that Oahu vacation home rentals make us feel more like residetns than tourists and provide a great alternative, especially for families with kids, like us.

Let's face it: People come to Oahu for different reasons and to experience different things. Similary, accommodations come in all styles, from luxury resorts to cottages. Staying in a house with a kitchen and all the related amenities offers a much more rewarding experience than booking a block of hotel rooms with no shared spaces. Even our new president chose this route, spending his 2008 winter holiday on Oahu in a private home in Kailua.

Before You Rent

If the idea of staying at a beachfront home on an island is your dream, you can make this a reality. And expcet to be impressed. But, with this expectation also comes a few caveats that you should investigate before your trip.

Find out what you're getting, prior to securing a vacation rental property. Be sure to visit the property Web sites, as you'll often find information to get you started, including, in some cases, online calendar/booking options.

Ask questions. Are there shared amenities with other guest, like pool, parking, etc.? Does the house offer Wi-Fi or provide beach equipment (surfboards, boogie boards, lounge chairs)? Many properties have guest limits and will increase the cost if you're over that limit. Some properties have rules on things like animals, quiet times and pool/jacuzzi hours. More often than not, the property owners do not reside on site but will have a manager, so talk with them.

Note: in some rental areas, properties are located off of major roads (as an example, several homes we rented from Hawaii Beach Homes are located off Kalanianiole Highway), rush hour traffic makes for a rude awakening (often as early as 5 a.m.) So again, ask for specifics.

Hawaii Hideaways

For drop-dead beautiful luxury rentals, Hawaii Hideaways has booking accss to about 60 private homes on Oahu (and about 200 throughout the whole of Hawaii). All are luxury, high-end properties, located either beacfront or with an ocean view and a pool, with sizes ranging from three-to eight-bedrooms, though its Grand Pavillion home (where President Obama and his family stayed) is a 10-bedroom property.

Services include a 24-hour concierge and hotel-like amenities, such as on-call massage, mani/pedi and spa services. Staff can also book accommodations to cater to guests' activity preferences-e.g., if a client wants to plan a surf vacation, Hawaii Hideaways can book a beachfront property with a surf break and arrange for private surf lessons.

Rates start at $800 per night or $6,500 per week and can go up to $10,000 per night or $70,000 per week, with a 50 percent deposit due at time of booking, and the balance due two months prior to the stay. According to Anne Pawsat-Dressler, president, advanced reservations are not necessarily needed as last-minute bookings are quite common, and the company is "known for brokering good deals at the last minute." However, if planning a very large family holiday stay, she does recommend reserving one year in advance.  

 http://www.travelmuse.com/articles/oahu/oahu-vacation-home-rental/2