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Diamond Head Vacation Rentals

Vacationing on the foothills of the most popular and photographed extinct volcano in the world is an experience of a lifetime! Most of the Diamond Head vacation rentals are vacation condos located on the Gold Coast of Waikiki. Here you will never be bored. You can go swimming at Kaimana Beach (a nice family beach, great for swimming and snorkeling), do Hawaii's most popular hike to the Diamond Head lookout, or just immerse yourself into the abundant selection of seaside shops and restaurants located along Waikiki's Kalakaua Avenue. Find your favorite Diamond Head vacation rental below.

  • Oceanfront Luxury Estate, Pool, Spa, Gourmet Kitchen, Theater, Steps to Beach

    MINIMUM REQUIREMENTS APPLY. INQUIRE FOR DETAILS. Designed to capture Island indoor-outdoor living, this 4 bedroom & 5.5 bath oceanfront home offers all of the features expected in a luxury home. Complete with a gourmet kitchen, and WOLF appliance...

    4 Bedrooms, 5 Bathrooms, Sleeps 10

    HI>Honolulu

    3,500 USD - 6,600 USD

    nightly

  • Convenient Location - Walk to Waikiki

    Beautiful remodeled spacious cottage style house. The house is fully furnished and is located in a very desirable neighborhood in Oahu. You can walk to Waikiki Beach, walk to the amazing Kapiolani Park, you can also go to The Zoo and the Aquarium...

    3 Bedrooms, 1 Bathrooms, Sleeps 10

    HI>Honolulu

  • Gold Coast Hideway at the Foot of Diamond Head

    This spacious two story home nestled in a quiet historic neighborhood at the base of Diamond Head. The second story has a long lanai with views of Diamond Head. This home has 3 bedrooms with a study that can also be used as a bedroom. All bedro...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Honolulu

  • Quiet Beachfront Home at the Base Of Diamond Head

    Please no party or event inquiries. As you drive onto the property of this Historic Home, built in 1937 by Charles W. Dickey and recently restored, you are greeted by your own private park. Native Kukui and Ulu trees rustle in the cool trade wi...

    3 Bedrooms, 4 Bathrooms, Sleeps 8

    HI>Honolulu

  • Diamond Head - Gold Coast Jewel - Ocean Views

    This Gold Coast Jewel has been completely renovated and divided into two separate living quarters (2bd/2ba upstairs; 2bd/1ba downstairs). Downstairs currently rented long term. Our renovated home provides shellstone counters and floors, (bamboo f...

    2 Bedrooms, 2 Bathrooms, Sleeps 5

    HI>Honolulu

  • Spectacular View - Luxury Living on a Private Beach Cove

    PLEASE SCROLL BELOW CALENDAR TO FIND RENTAL RATES. *NO EVENTS/WEDDING Elegant, Hawaiian style, 4600 sq. ft. home with spectacular ocean views and lush, tropical gardens. Located 100 feet from the ocean in a secluded beach-side community, the ho...

    4 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Honolulu

  • Xmas and New Year Special $300 off

    Gold Coast - foothills of Diamond Head area ! Great lifestyle living in this area because it is within walking distance to two private clubs and several famous beaches such as Waikiki Beach. Not to mention you are across the street from the Kapio...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Honolulu

  • NEXT AVAILABILITY - August 23-31,2016 -- SPECIAL RATE

    Sans Souci is an 80% 'owner occupied' building consisting of 12 floors plus 3 penthouse apartments (88 units total). All entrances require a security key. Garage parking space is assigned and within the secured area. Laundry facilities are on t...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Honolulu

    875 USD - 875 USD

    weekly

    3,000 USD - 3,000 USD

    monthly

  • GOLD COAST HOME - TWO BEDROOM OCEAN VIEW (Sleeps 6) STEPS FROM THE OCEAN!

    TAT# W78510761-01 *THIS PROPERTY IS ONLY AVAILABLE FOR THE MONTHLY RATE* Beautiful, quaint, newly remodeled home located steps from the ocean at Diamond Head. Complete remodel finished December 2013. Perfect location to explore the island from. ...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Honolulu

  • Gorgeous Remodeled Colony Surf, Hi-Speed Internet March 2016 Special

    This beautiful, remodeled and updated luxury condo with high-speed internet access is on the eighth floor of the prestigious Colony Surf beachfront building. The condo apartment is decorated in a relaxing island style with pastel shades throughout...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Honolulu

  • Gorgeous Diamond Head Ocean Front Lg 2 Bdrm Condo. Ocean Views and water access

    After lounging around in your 2nd floor oceanfront condominium, (Overhead fans , air conditioning or just the amazing ocean breezes) walk across the street to the 108-acre Queen Kapiolani Park with tennis courts, running trails, picnic areas, arch...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Honolulu

    1,925 USD - 1,925 USD

    weekly

    8,250 USD - 8,250 USD

    monthly

  • Upscale 900 SF Colony Surf Condo - Beachfront

    PLEASE NOTE THAT WE HAVE BEEN ON THIS VRBO WEB SITE SINCE YEAR 2000. WE ELECT NOT TO USE ONLINE BOOKING THROUGH VRBO, IN ORDER TO SAVE YOU THE NEW 5.5% (APPROX. $200+ PER MONTH) VRBO SERVICE FEE. May, 2017 is the first available month. . As alwa...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Honolulu