Kailua Vacation Rentals - Privately Owned Professionally Managed®

Come discover Oahu and unwind on our wonderful world renowned tropical beaches, visit our historic Pearl Harbor, play in the Waikiki surf, or hike along Leahi (Diamond Head). Oahu presents a delicate mix of the sophisticated West and our traditional native Hawaiian cultures creating an exotic blend of past and present. We invite you to view the finest selection of vacation rentals on our beautiful Hawaiian Island of Oahu.


Marni - Emerald Kite Destination Agent

Call Our Local Agents 7 Days a Week from 9am - 10pm EST

USA: 808.650.3995

International: +1 941.500.4555

Our Most Popular 5+ Bedroom Kailua Rentals

Kailua Beach House Vacation Rental Luxury all the Way!

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 6 Bedrooms
  • 4 Bathrooms

Upscale Six Bedroom Home Rental on Kailua. Call Agent Today.

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Kailua Vacation Home Rental Sleeps Ten Guests Private Pool

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 5 Bathrooms

Our Most Popular 4 Bedroom Kailua Rentals

Kailua Vacation Home Sleeps Eight Guests.

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Our Most Popular 2 Bedroom Kailua Rentals

Kailua Condo 896053

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  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Kailua Condo 896054

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  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Our Most Popular 1 Bedroom Kailua Rentals

Kailua Condo 896055

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  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 1 Bedroom
  • 2 Bathrooms

Dining in Oahu is simply delectable and the influence of Japanese, Portuguese, Korean and Indonesian cultures are reflected in the delicate fusion cuisine that Hawaii is renowned for. Locally caught seafood is at the top of most menus and let’s not forgets to make a reservation for a traditional Hawaiian Luau.

Oahu shopping is the best in all of Hawaii and while local arts and crafts are abundant you’ll find a wide array of world-class malls such as Ala Moana Center, Windward Mall and Kahala Mall.  Shop in         Waikiki’s DFS Galleria and the Royal Hawaiian Center where you will find an abundance of Hawaiian jewelry, arts, crafts, and exclusive designer fashions.

The nearest major airport is Honolulu International Airport (HNL / PHNL). Situated 9 miles from the center of Waikiki. Another major airport is Molokai Airport (MKK / PHMK) which is located approximately 48 miles from Waikiki.