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.

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  • Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach

    Treat yourself to ultimate island luxury in this architecturally designed $5.5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite ...
    Registration Number: TA-047-203-9424-01, 350020180000, GE-047-203-9424-01

    • 4 bedroom
    • 6 bathroom
    • Sleeps 9
    Hawaii> Honolulu
    18  reviews
    from $690 
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  • Ocean View Diamond Head Kahala Slope

    Gated custom designed immaculate contemporary ocean view home with outdoor deck, covered lanai, unheated pool and heated jet spa in quiet Diamond Head Kahala cul-de-sac on Diamond Head Crater slope. Ocean and Koolau mountain views from every ...
    Registration Number: 131048062000, GE-098-016-0512-01, TA-098-016-0512-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    24  reviews
    from $730 
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  • Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise

    Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, ...
    Registration Number: 330310160000, GE-107-728-0768-01, TA-107-728-0768-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    23  reviews
    from $188 
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  • Family fun Cottage w/Private Pool,A/C, walk to Beach and shops, Kahala Cottage

    This home-away-from-home exudes island style and comfort! Open, airy Kahala Cottage features two charming living spaces, a nicely-appointed kitchen, and a dedicated dining area that allow guests to enjoy quality time together at home. Flexible ...
    Registration Number: 350150260000, TA-038-170-4192-01, GE-038-170-4192-01

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    6  reviews
    from $434 
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  • Beachfront, Kahala Mini Resort, w/2 pools, private tennis court, gated, A/C

    For discounted rates on Main house only, please inquire. 12 Night Minimum over the Christmas/New Years Holiday Season.

    Spacious beachfront estate is situated on lush tropical grounds, nestled in between palm trees. Enter the grounds ...
    Registration Number: 350060160000, GE-005-323-3664-01, TA-005-323-3664-01

    • 7 bedroom
    • 7 bathroom
    • Sleeps 14
    Hawaii> Honolulu
    10  reviews
    from $4,450 
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  • This house is a 7 bedroom(s), 6 bathrooms, located in Honolulu, HI.

    **If you need a smaller trip duration that what is posted, please send us a direct inquiry with the group size and preferred stay length.**

    UNPARALLELED VIEWS!
    Endless hypnotizing panoramic views await you from this well maintained 7 ...
    Registration Number: GE-007-362-3552-01,TA-007-362-3552-01,1350230020058

    • 7 bedroom
    • 6 bathroom
    • Sleeps 16
    Hawaii> Honolulu
    7  reviews
    from $1,428 
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  • Kahala Beach Ocean Front & Pool View

    The Kahala Beach Condo Is Fully Renovated with Koa Wood Flooring Throughout.

    Modern Asian Inspired Furnishings & Conveniences Such As Free Wi-Fi, Long Distance Calling To Canada, USA and Mexico, Dvr with Movie Channels Round Out this ...
    Registration Number: GE-177-124-3520-01, TA-177-124-3520-01, 350230020072

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    2  reviews
    from $300 
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  • Kahala Oceanside- 6 Bed/6 1/2 bath/Sleeps 14

    Kahala Oceanside is a private paradise retreat that comfortably sleeps 14. This luxurious ocean front hideaway on the South Shore of Oahu, known for its spectacular sunsets, is just minutes away from fine eateries, world-famous hikes, and the ...
    Registration Number: GE-053-250-7136-01, TA-053-250-7136-01, 1350030350000

    • 6 bedroom
    • 7 bathroom
    • Sleeps 15
    Hawaii> Honolulu
    15  reviews
    from $3,523 
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  • It's paradise! Come & experience the calmness & serenity with the birds singing!

    STUNNING new home with views of Diamond Head, the ocean and Waikiki. Super spacious of 1980 sq. ft., immaculate 3 bedrooms (4 BEDS! King bed & 3 queen beds) and 2 full bathrooms, open floor plan, huge and well equipped kitchen with cookware, ...
    Registration Number: TA-048-102-1952-01,+GE-048-102-1952-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Honolulu
    1  reviews
    from $195 
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  • Charming Historical Home - Crutchfield Estate

    This spectacular French Tudor exudes a casual elegance and the comfort of the islands. Inside you will find gleaming wood floors, an elegant fireplace, crown molding and spacious bright rooms. The kitchen is fully equipped with a new ...
    Registration Number: TA-112-501-9648-01,+GE-112-501-9648-01

    • 4 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    2  reviews
    from $1,350 
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  • Luxury Oceanfront Estate: Royal Kahala Estate

    Royal Kahala Estate is Oahu’s most luxurious vacation rental near the foot of Diamond Head. The exquisite home features seven bedrooms, eight full baths, and a half-bath, encompassing 14,000 square feet all within a private beachfront estate. ...
    Registration Number: 350020500000, GE-199-064-7808-01, TA-199-064-7808-01

    • 8 bedroom
    • 10 bathroom
    • Sleeps 16
    Hawaii> Honolulu
    6  reviews
    from $3,429 
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  • Historic Home+guest cottage in Kahala near the Beach w/Pool & AC: Ho'okipa Villa

    Kahala Luxury Living

    Welcome to Ho'okipa Villa! Built in 1938 and recently renovated, this luxury home offers a unique combination of vintage and modern beach charm. Four bedrooms and three bathrooms comprise the main home, including the...
    Registration Number: 350100100000, TA-088-184-4224-01, GE-088-184-4224-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    5  reviews
    from $485 
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  • Modern Tropical Home w/Pool, Private Yard, & A/C. Kahala Breeze

    Experience the laidback luxury and authentic island living of Kahala Breeze, a spacious four-bedroom home that features elegant decor and design cohesive with the natural beauty that surrounds it. 

    An abundance of windows in the living ...
    Registration Number: GE-065-534-9760-01, TA-065-534-9760-01, 350030310000

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    4  reviews
    from $653 
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  • Cottage with Private Salt Water Pool

    30 night minimum
    This beautiful recently updated cottage is nestled in the quiet, safe, and upscale neighborhood of Kahala. Excellent location! Just minutes to Waikiki, nearby parks and the pretty white-sand beaches of the East Honolulu ...
    Registration Number: GE-108-852-8384-01, 13526023, TA-108-852-8384-01

    • 0 bedroom
    • 0 bathroom
    • Sleeps 5
    Hawaii> Honolulu
    3  reviews
    from $250 
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  • Charming Studio Near Kahala Beach

    The perfect studio for a couple on their Hawaiian get-away who want to live like locals during their stay. Please inquire about your specific dates and we can try to accommodate your stay with a 7 day minimum stay. This beautiful and spacious ...
    Registration Number: TA-094-014-7712-01, 1350300320000, GE-151-279-8208-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Honolulu
    38  reviews
    from $295 
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  • Beautiful Nautical-Themed Home w/AC, Yard, Private Pool & Spa: Kahala Seaside

    Welcome to Kahala Seaside, a spacious two-story garden view home featuring four bedrooms, three-and-a-half bathrooms, and lush garden views. Nestled in the upscale seaside burg of Kahala, you’ll have access to all the fun and excitement of ...
    Registration Number: 350040510000, GE-188-470-4768-01, TA-188-470-4768-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 7
    Hawaii> Honolulu
    1  reviews
    from $667 
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  • Luxury Resort Style Living at it's Best!

    Our Kahala Beach Apartment sits on one of the most valuable strips of beachfront in Hawaii. This Elegant apartment is Beachfront resort-style Living at its best. The Apartment is steps away from the 4 star Kahala Hotel with its Elegant dining ...
    Registration Number: TA-143-627-7248-01, GE-143-627-7248-01, 350230020174

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    1  reviews
    from $633 
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  • Luxurious Oceanfront Estate w/Pool & Hot tub, Panoramic Views, Kaiko'o Villa

    NEWLY RENOVATED!
    Your very own oceanfront oasis awaits you at Kaiko’o Villa, a premier 4 bedroom and 4 bathroom estate residing on the cliffs of scenic Oahu. When you traverse through the doors of this Balinese-inspired vacation rental, ...
    Registration Number: 310410210000, TA-096-182-0672-01, GE-096-182-0672-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    2  reviews
    from $3,025 
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  • This house is a 7 bedroom(s), 5 bathrooms, located in Honolulu, HI.

    **If you need a smaller trip duration that what is posted, please send us a direct inquiry with the group size and preferred stay length.**

    UNPARALLELED VIEWS!
    Endless hypnotizing panoramic views await you from this well maintained 7 ...
    Registration Number: GE-007-362-3552-01,TA-007-362-3552-01,1350230020058

    • 7 bedroom
    • 5 bathroom
    • Sleeps 16
    Hawaii> Honolulu
    1  reviews
    from $998 
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  • Close to Kahala Beach/Air Conditioning/Heated Pool/Clean/Quiet Neighborhood

    Elegantly remodeled in 2018, this one level, very clean, 4 bedroom & 3 bath home, has 2 master suites, a gourmet kitchen, air conditioning in every bedroom & high end finishes throughout this private oasis. Please inquire about your specific ...
    Registration Number: 1350300320000, GE-094-014-7712-01, TA-094-014-7712-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    7  reviews
    from $2,000 
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  • Exclusive & Private Gated Estate, Large Family Oasis Hideaway.


    Elegant, private, tropical gated estate, with lots of room to enjoy your family.
    Kahala Luxury is a spacious 6 Bedroom, 6 1/2 Bath home located in the heart of residential Kahala and is a wonderful home to spend precious family time.
    ...
    Registration Number: 350070050000, TA-153-997-3120-01, GE-153-997-3120-01

    • 5 bedroom
    • 7 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    21  reviews
    from $1,850 
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  • Paradise Rental w/ Pool & Spa - 30 day min

    Let us welcome you to Ohana Paradise, a sophisticated, tropical retreat located in one of the most affluent and prestigious areas of Diamond Head-Kahala, world renowned for its beauty, beaches, parks, restaurants, and family fun. Leave the ...
    Registration Number: GE-203-504-0256-01,TA-203-504-0256-01

    • 6 bedroom
    • 5 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    19  reviews
    from $625 
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  • This townhouse is a 4 bedroom(s), 3 bathrooms, located in Honolulu, HI.

    **If you need a smaller trip duration that what is posted, please send us a direct inquiry with the group size and preferred stay length.**

    UNPARALLELED VIEWS!
    Endless hypnotizing panoramic views await you from this well maintained 4 ...
    Registration Number: GE-007-362-3552-01,TA-007-362-3552-01,1350230020058

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    37  reviews
    from $453 
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  • Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath

    Upscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the nearest beach, Kahala Hotel, Waialae Country club. 6-minute drive to the world famous Waikiki Beach, Diamond Head hiking, Rainbow's ...
    Registration Number: TA-008-444-7232-01, GE-008-444-7232-01, 230360390448

    • 5 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    130  reviews
    from $850 
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  • Magnificent Waikiki Mountain Views! Free Parking, Wi-Fi, Pool & More!

    Waikiki Sunset #2503 – 229 Paoakalani Ave.

    NEW TO OUR INVENTORY! Enjoy the lush greenery of the Ko'olau Mountains and exquisite Hawaiian trade winds from your private lanai! This cozy rental features central A/C, a full kitchen, free ...
    Registration Number: TA-159-961-1904-01, GE-159-961-1904-01, 260280110249

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Honolulu
    14  reviews
    from $296 
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  • This townhouse is a 3 bedroom(s), 3 bathrooms, located in Honolulu, HI.

    **If you need a smaller trip duration that what is posted, please send us a direct inquiry with the group size and preferred stay length.**

    UNPARALLELED VIEWS!
    Endless hypnotizing panoramic views await you from this well maintained 3 ...
    Registration Number: GE-007-362-3552-01,TA-007-362-3552-01,1350230020058

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    87  reviews
    from $714 
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  • Oahu's Perfect Island Getaway...5 Minutes From Waikiki

    This lower level beautifully 2 bedroom, 2 bath home, 980 Sq. ft is perfect for enjoying your Hawaii vacation. This is an attached 2 bedroom, 2 bath fully equipped home with its own separate entrance. This home comfortably sleeps 4 adults. There...
    Registration Number: GE-189-110-4768-01, 1280300620000, TA-189-110-4768-01

    • 2 bedroom
    • 2 bathroom
    • Sleeps 5
    Hawaii> Honolulu
    12  reviews
    from $250 
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  • The Gingerbread House sleeps 10 & Kahala Beach is just across the street

    The Historic Gingerbread House is a secure and gated residence directly across the street from Kahala beach. The neighborhood is between Diamond Head, the Kahala Hotel and the Waialae Country Club where the world renowned Sony Open is held. Our ...
    Registration Number: 350040120000, TA-019-756-4416-01, GE-019-756-4416-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    45  reviews
    from $825 
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  • BIG ALOHA & AWESOME VIEW AT THIS HAWAIIAN HOME!

    ~Breezy Spacious and Welcoming Vacation Home~
    This Hawaiian home sits up on the mountain with unbelievable, panoramic views of the Pacific Ocean, Diamond Head, Waikiki, and downtown. Watch sunsets, fireworks, whales, and rainbows from the ...
    Registration Number: 330310320000, TA-122-615-2448-01, GE-122-615-2448-01

    • 3 bedroom
    • 3 bathroom
    • Sleeps 7
    Hawaii> Honolulu
    100  reviews
    from $210 
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  • Charming Spanish Colonial Historic Home w/Ocean Views, A/C - Near Waikiki

    A 10-minute walk from Waikiki, discover your own private paradise nestled at the base of Diamond Head in Honolulu’s renowned Gold Coast. Built in 1926 and beautifully remodeled with modern luxuries, Hale Mahie is notable as an example of the ...
    Registration Number: TA-044-602-3680-01, GE-044-602-3680-01, 310330200000

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    7  reviews
    from $532 
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