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 Toll Free: 808.650.3995

International: +1 941.500.4555

Our Most Popular 5+ Bedroom Kailua Rentals

Kailua Home 896344

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 8 Bedrooms
  • 8 Bathrooms
  • Property #896344
  • Available
  • Average $13500 per Night plus taxes and fees
  • Map Request Quote

Kailua Home 896304

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 5 Bedrooms
  • 5 Bathrooms
  • Property #896304
  • Available
  • Average $1200 per Night plus taxes and fees
  • Map Request Quote

Luxury Beachfront Vacation Villa with Pool

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 10 Bedrooms
  • 10+ Bathrooms
  • Property #896925
  • Available
  • Average $11895-19795 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 4 Bedroom Kailua Rentals

Luxury Villa in Kailua Experience Real Hawaii Living

  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms
  • Property #895955
  • Available
  • Average $1853 per Night plus taxes and fees
  • Map Request Quote

Kailua Home 896246

  • Gold
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms
  • Property #896246
  • Available
  • Average $900 per Night plus taxes and fees
  • Map Request Quote

The Ultimate Most Beautiful of Vacation Homes - Beach House

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms
  • Property #896743
  • Available
  • Average $1,595-2,495 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 2 Bedroom Kailua Rentals

Kailua Condo 896053

  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms
  • Property #896053
  • Available
  • Average $119 per Night plus taxes and fees
  • Map Request Quote

Kailua Condo 896054

  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms
  • Property #896054
  • Available
  • Average $149 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 1 Bedroom Kailua Rentals

Kailua Condo 896055

  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 1 Bedroom
  • 2 Bathrooms
  • Property #896055
  • Available
  • Average $139 per Night plus taxes and fees
  • Map Request Quote

Kailua Condo 883435

  • Silver
  • Condo
  • No Pool
  • Max Occupancy: 2
  • 1 Bedroom
  • 1 Bathroom
  • Property #883435
  • Available
  • Average $235 per Night plus taxes and fees
  • Map Request Quote
Marni - Emerald Kite Destination Agent

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

USA Toll Free: 808.650.3995

International: +1 941.500.4555

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.