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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 1 bdrm best location free parking private beach washer/dryer

    Affordable luxury on Hawaii's most exclusive water front address! Castle Surf is the most sought after building because it is small, friendly and easy to live in. Parking space is very accessible to the unit. Charming and spacious 800 sq foot c...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Honolulu

    117 USD - 167 USD

    nightly

    5,000 USD - 5,000 USD

    monthly

  • Delightful Hawaiian Cottage Style Oceanfront Studio Apartment

    “The Cottage” is a sunny, charming 'Hawaiiana-style' unit ocean view studio condominium on one of the upper floors of the Diamond Head Beach Hotel and Residences on the Gold Coast of Waikiki. Lovingly furnished by its Owner, its a 'home-away-from...

    0 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Honolulu

    140 USD - 140 USD

    nightly

    950 USD - 950 USD

    weekly

    2,250 USD - 2,250 USD

    monthly

  • 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

  • Diamond Head, Pool, AC, Walk from Waikiki & Beach, Beautiful Interiors

    Large open floor plan, central AC and freshwater pool with spa make this home the perfect getaway. Second level features a master suite with view of Diamond Head and den. This highly sought after location is steps to some of the best beaches and s...

    3 Bedrooms, 1 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

  • Hawaiian Luxury Living

    Hawaiian living at its best. Wake to the spectacular ocean view. Sleep to the sound of waves and palm trees. Just a few steps to the beach where you can enjoy surfing, kayaking, paddle boarding, snorkelling, swimming or just a good bain de soleil...

    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

  • Black Point Villa Located in Exclusive, Gated Community, Private Pool, Walk to Beach

    MINIMUM REQUIREMENTS APPLY. INQUIRE FOR DETAILS. This one of a kind villa sits high a top the private gated community of Black Point, in one of the most exclusive locations on Oahu's south shore. Oahu's south shore is the top location for touris...

    4 Bedrooms, 3 Bathrooms, Sleeps 10

    HI>Honolulu

  • Hidden D.H. Estate Paradise-Truly in Diamond Head Neighborhood

    Hidden Diamond Head Estate Paradise located in a truly Diamond Head District, is nestled above world famous Waikiki Beach, in a secluded, tropical, tranquil environment directly below Diamond Head’s Le’ahi Peak State Monument (one of the best know...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Honolulu

    1,600 USD - 2,100 USD

    weekly

    4,500 USD - 5,000 USD

    monthly

  • Ocean front condo, diamoned head

    Large 1200sq feet studio, ocean front condo, AMAZING!! sunsets and ocean view as well as Waikiki skyline views. Comes with 1 assigned parking stall. The unit is on very HIGH floor very private and 1 floor below the pent house. Condo is diamond ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Honolulu