Get the inside scoop on Oahu vacation home rentals, where you can live like a local and experience the essence of tropical living.
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 residents 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. Similarly, 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.
If the idea of staying at a beachfront home on an island is your dream, you can make this a reality. And expect 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 guests, 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). Depending on the house’s proximity to the highway, rush hour traffic makes for a rude awakening (often as early as 5 a.m.) So again, ask for specifics.
Depending on where you stay on the island, vacation homes, along with bed and breakfasts, are easy to find. But it’s worth noting that similar to what’s happening on other Hawaiian islands (see Maui B&B Battles sidebar), there is a move to decrease the number of rentals and B&Bs on Oahu, in particular in the Kailua and Lanikai areas.
While most B&Bs are legal, some are not. When considering booking a rental property, play it safe and inquire. At a minimum, ask the booking agent or property manager if the property holds a Non-Conforming Use Certificate or zoning variance that allows them to operate as a B&B, and try to get as much information as you can to ensure your arrangement is legal.
Below are several of the providers I’ve either rented from or referred friends to over the past two decades.
With more than 30 years pioneering this alterative form of vacationing, Hawaii Beach Homes offers access to more than 40 homes, primarily on the South and North Shore of Oahu; they do not offer rental homes in Kailua or Lanikai. Started in the 1970s, the owners maintain a base of mostly beachfront properties, with concierge services available (housekeeping, baby equipment, private chef, massage and grocery shopping services) for those guests who want additional attention.
The company provides the full range of homes from cottages to executive homes, but its style is really well suited to family-friendly home rentals in exceptional locations such as Lanikea, where you might even have a chance to swim with turtles. Like many who use Hawaii Beach Homes, I am a repeat client. I appreciate the fact that the homes are professionally managed by a team residing on Oahu who not only know the island but also provide recourse if something is needed. Prices vary depending on style/size of the home, number of guests, seasonal factors, etc., but a general average is about $50 per person per night.
Note: Be sure to ask the rental company about seasonal rates, discounts and last minute specials, which you can also find on its Web site.
Hawaiian Beach Rentals is a solid starting point for travelers looking to stay in luxury or high-end homes on Oahu, and it includes rentals on Kailua and Lanikai beaches, two of the world’s top-rated and pristine beach areas. The company is also favored by a VIP customer list of musicians, royalty, politicians, actors and sports figures (no names released publicly).
Properties in its portfolio range from one to seven bedrooms and include the Paul Mitchell Estate (Lanikai, $5,500 to $7,500 per night) and Oahu Lani ($7,500 per night), which features indoor/outdoor wading pools, an outdoor hot tub, a game room, nursery and entertainment area, concierge, chef and daily room cleaning. There also are plenty of more affordable homes to choose from for $300 to $800 per night. The company claims to have the largest selection of alternative (non-hotel) rentals in Hawaii, and its inventory is impressive. In addition, the company’s agents reside in Hawaii, which allows them to provide an insider’s look and tips to truly experiencing Oahu.
Like Hawaii Beach Homes, the company’s Web site offers a last minute “vacation deals” and a price-match guarantee for nearly 1,000 of its units—so rates are competitive.
For drop-dead beautiful luxury rentals, Hawaii Hideaways has booking access to about 60 private homes on Oahu (and about 200 throughout the whole of Hawaii). All are luxury, high-end properties, located either beachfront 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 surfing 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 the 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.
Another option specific to the Kailua area is Hawaii’s 10 Best Vacation Homes, which offers access to more than 20 Kailua gems. With a collection of executive homes as well as traditional B&Bs and beach cottages, the owners help visitors, from the budget-minded traveler to larger families to entire wedding parties.
Prices on rentals often depend on the season as well as number of bedrooms, length of stay, number of guests and area of Oahu. While some accommodations are available on a nightly rental basis (though several require a multiple-night stay), the houses are available only by the month. Prices range from $85 per night for a double in a guesthouse to $19,000 per month for the top beachfront house.
I was unable to follow the link to the Hawaii's 10 Best Vacation Homes. But, I do have to point out one that is available now that is a $36 million dollar property The Royal Kailua Estate Check it out.