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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.

  • 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: 350020180000, GE-047-203-9424-01, TA-047-203-9424-01

    • 4 bedroom
    • 6 bathroom
    • Sleeps 9
    Hawaii> Honolulu
    from $1,256 
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  • Island Adventure: Minivan Rental, Contact Us for Stays Under 30 Days

    **Short Stays Welcome!** While local regulations prevent us from advertising rentals for less than 30 days, we're happy to accommodate shorter stays within a 30-day booking window. If you're looking for a stay under 30 days, please reach out to ...
    Registration Number: GE-123-456-7890-01, TA-123-456-7890-01

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    from $469 
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  • Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath

    **Minimum 30 days required for reservation**
    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 ...
    Registration Number: 230360390448, TA-008-444-7232-01, GE-008-444-7232-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    from $530 
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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: GE-107-728-0768-01, TA-107-728-0768-01, 330310160000

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    from $232 
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  • Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops

    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: TA-038-170-4192-01, GE-038-170-4192-01, 350150260000

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    from $454 
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  • Fall Price Drop! Exclusive & Private Gated Estate, Large Family Oasis Hideaway


    Elegant, private, tropical gated estate, with lots of room to enjoy your family.
    Once you have booked, contact us regarding your actual stay dates for price.
    Kahala Luxury is a spacious 6 Bedroom, 6 1/2 Bath home located in the heart ...
    Registration Number: 350070050000, TA-153-997-3120-01, GE-153-997-3120-01

    • 5 bedroom
    • 7 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    from $802 
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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: GE-005-323-3664-01, TA-005-323-3664-01, 350060160000

    • 7 bedroom
    • 7 bathroom
    • Sleeps 14
    Hawaii> Honolulu
    from $7,289 
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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: 1350030350000, GE-053-250-7136-01, TA-053-250-7136-01

    • 6 bedroom
    • 7 bathroom
    • Sleeps 15
    Hawaii> Honolulu
    from $4,583 
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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
    from $1,602 
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  • 10% Off Summer Special! Luxury Oceanfront Estate: Banyan House

    Prices start at $150,000/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

    Banyan House is Oahu’s most luxurious vacation rental near the foot of Diamond Head. The exquisite home features...
    Registration Number: TA-199-064-7808-01, GE-199-064-7808-01, 350020500000

    • 8 bedroom
    • 10 bathroom
    • Sleeps 16
    Hawaii> Honolulu
    from $6,131 
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  • Ho'okipa Villa: Historic Home+guest cottage in Kahala near the Beach w/Pool & AC

    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: TA-088-184-4224-01, 350100100000, GE-088-184-4224-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    from $696 
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  • Comfort and Elegance with stunning views of Diamond Head

    Newly renovated 3 bedroom, 2.5 bath home on Maunalani Hts. Tastefully furnished with high quality bedroom, living room and dining room furniture. HD Smart T.V.s in living room, kitchen and bedroom. Fully functional kitchen with new dishes, ...
    Registration Number: TA-187-879-4240-02, 330180700000, GE-186-879-4240-01

    • 0 bedroom
    • 0 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    from $267 
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  • Kahala Breeze: 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: 350030310000, TA-065-534-9760-01, GE-065-534-9760-01

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    from $739 
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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: TA-108-852-8384-01, GE-108-852-8384-01, 13526023

    • 0 bedroom
    • 1 bathroom
    • Sleeps 5
    Hawaii> Honolulu
    from $206 
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  • Steps to Kahala Beach, quiet, King bed, patio, parking, A/C, kitchenette & BBQ

    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. This beautiful and spacious studio with 1 bathroom is ...
    Registration Number: TA-094-014-7712-01, GE-151-279-8208-01, 1350300320000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Honolulu
    from $284 
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  • Kahala Seaside: Beautiful Nautical-Themed Home w/AC, Yard, Private Pool & Spa!

    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, TA-188-470-4768-01, GE-188-470-4768-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 7
    Hawaii> Honolulu
    from $585 
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  • Hale Moana~Beachfront

    * For less than 30 day stays, please send a email onlineweb- OceanViewOahu

    At the Kahala Beach Apartments, savor the best of island life by lounging at the immaculate white sandy beach, take a plunge in the complex's luxurious ocean-front...
    Registration Number: GE-007-362-3552-01, TA-007-362-3552-01, 1350230020058

    • 3 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    from $397 
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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: GE-094-014-7712-01, TA-094-014-7712-01, 1350300320000

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    from $2,609 
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  • KAHALA BEACH APARTMENT

    FORGET YOUR WORRIES IN THIS SPACIOUS AND SERENE SPACE. THIS MODERN RESIDENCE IS NEWLY RENOVATED AND EXTREMELY CLEAN. LOCATED ON THE BEAUTIFUL KAHALA BEACH. UNIT OFFERS PRIVATE OUTDOOR PATIO WITH SEATING AND DINING TABLE TO HELP YOU ENJOY THE ...
    Registration Number: TA-058-184-0896-01, 350230020118, GE-058-184-0896-02

    • 2 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    from $300 
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  • Beachfront Condo! Beautiful Beach!

    Experience unparalleled luxury in this Oahu gem, perfectly positioned between the esteemed Waialae Country Club and the illustrious Kahala Hotel. Just a whisper away from the beach, this condo offers an intimate escape from Waikiki's fervor, yet...
    Registration Number: TA-130-276-7104-01, GE-130-276-7104-01, 350230020018

    • 2 bedroom
    • 2 bathroom
    • Sleeps 5
    Hawaii> Honolulu
    from $320 
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