Diamond Head 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: (866) 922-0575

International: +1 305-425-1750

Our Most Popular 5+ Bedroom Diamond Head Rentals

Diamond Head Seven Bedroom Vacation Rental - Full Ocean View

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy:
  • 7 Bedrooms
  • 7 Bathrooms
  • Property #877614
  • Available
  • Average $7600 per Night plus taxes and fees
  • Map Request Quote

Diamond Head Vacation Home- Contemporary Chic

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 6 Bathrooms
  • Property #895534
  • Available
  • Average $1750 per Night plus taxes and fees
  • Map Request Quote

Diamond Head Home 895897

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 5 Bedrooms
  • 4 Bathrooms
  • Property #895897
  • Available
  • Average $1250 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 4 Bedroom Diamond Head Rentals

Oahu Luxury Estate Beachfront and the Ultimate Views

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms
  • Property #895579
  • Available
  • Average $1535 per Night plus taxes and fees
  • Map Request Quote

Diamond Head Four Bedroom Luxury Rental Property Oahu

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms
  • Property #895620
  • Available
  • Average $2000 per Night plus taxes and fees
  • Map Request Quote

Diamond Head Beachfront Luxury Vacation Rental Home

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms
  • Property #895674
  • Available
  • Average $4500 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 3 Bedroom Diamond Head Rentals

Diamond Head Home 895669

  • Platinum
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 4 Bathrooms
  • Property #895669
  • Available
  • Average $2500 per Night plus taxes and fees
  • Map Request Quote

Three Bedroom Retreat Sleeps 6 Just 3 Minutes Drive to Beach

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms
  • Property #896864
  • Available
  • Average $6,895-9,395 per Night plus taxes and fees
  • Map Request Quote

Diamond Head Luxury Vacation Rental Home with Views

  • Gold
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 4 Bathrooms
  • Property #895622
  • Available
  • Average $2500 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: (866) 922-0575

International: +1 305-425-1750

Play at Kailua Beach against the cosmopolitan back drop of Honolulu or embrace our historic architecture and timeless spiritual traditions by visiting our many museums and historical sites.  Oahu is also home to Hawaii’s top tourist destination, Pearl Harbor. For the adventurous visitors, let’s not forget a must do hike along magnificent Diamond Head.

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.