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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.

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  • 7 Bedroom Estate with 2 pools, jacuzzi, private tennis court, gated

    Spacious beachfront estate is situated on lush tropical grounds, nestled in between palm trees. Enter the grounds thru the privacy gate to enjoy...

    • 7 bedroom
    • 7 bathroom
    • Sleeps 14
    HI> Honolulu
    7 night min stay1  reviews
    $3,675 per night
      Book Now
  • It's paradise! Come & experience the calmness & serenity with the birds singing!

    Beautiful new home, very quiet with view of Diamond Head, ocean and Waikiki. Super spacious of 1780 sq. ft., 3 bedrooms/2 bathrooms, open floor ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Honolulu
    10 night min stay1  reviews
    $521 per night
      Book Now
  • Private Quiet Seperate Studio

    Private 400 studio with a natural breeze. Quiet valley living. Only 2 miles to waikiki beach. Seperate unit from main house. Private entrance, ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    HI> Honolulu
    3 night min stay1  reviews
    $75 per night
      Book Now
  • 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 ...

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Honolulu
    7 night min stay26  reviews
    $1,725 per night
      Book Now
  • Luxury Modern Oceanview Villa built by Architect walking distance to

    Beautifully appointed and maintained, large 5,000 square foot elegant home in Oahu's most prestigious neighborhood. Open floor plan, beautiful ...

    • 4 bedroom
    • 5 bathroom
    • Sleeps 10
    HI> Honolulu
    7 night min stay5  reviews
    $1,400 per night
      Book Now
  • Luxury Tropical Oasis Kahala Home

    Come and experience a luxury island style right here in Kahala. This 3146 sq. foot 4 bedroom, 4.5 bath luxury estate is on one of the largest ...

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    HI> Honolulu
    10 night min stay3  reviews
    $1,750 per night
      Book Now
  • 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 ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Honolulu
    5 night min stay16  reviews
    $250 per night
      Book Now
  • Kahala Beach Ocean Front & Garden View 2 Bedroom/Bath

    The Kahala Beach Condo Is Fully Renovated with Koa Wood Flooring Throughout. Modern Asian Inspired Furnishings & Conveniences Such As Free ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Honolulu
    30 night min stay1  reviews
    $250 per night
      Book Now
  • Secluded Mountain Top Home

    NEW LISTING - INTRODUCTORY PRICE THROUGH NOVEMBER 2017!! Hale Mauka, which means Mountain House, provides a rare Hawaiian vacation opportunity ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 8
    HI> Honolulu
    3 night min stay1  reviews
    $500 per night
      Book Now
  • Private Resort Living Near Famous Kahala Beach

    This recently built 2 story Kahala home is like your own private resort, with complete privacy behind coral-rock stone walls and lush ...

    • 4 bedroom
    • 6 bathroom
    • Sleeps 8
    HI> Honolulu
    10 night min stay1  reviews
    $1,100 per night
      Book Now
  • 150-200 yards from Kahala Beach Park

    1000 sq ft studio with 2 partitioned bedrooms with queen beds, washer/dryer, stove, microwave, coffee maker, pool, outdoor barbecue & dining ...

    • 0 bedroom
    • 1 bathroom
    • Sleeps 4
    HI> Honolulu
    7 night min stay7  reviews
    $186 per night
      Book Now
  • ESCAPE TO HAWAIIAN PARADISE~ STEPS TO THE BEACH POOL & SPA A/C IMMACULATE

    HIGH SPEED INTERNET & WIFI CENTRAL AIR CONDITIONING FLAT SCREEN TV'S NETFLIX/AMAZON TV CUSTOM POOL & SPA COVERED LANAI BUILT IN GAS BBQ ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    HI> Honolulu
    10 night min stay29  reviews
    $945 per night
      Book Now
  • Gorgeous Estate on the Slopes of Diamond Head

    Treat yourself to ultimate island luxury in this architecturally designed $4M home on 15,000 sq ft lot in one of the most desired locations on ...

    • 4 bedroom
    • 6 bathroom
    • Sleeps 9
    HI> Honolulu
    10 night min stay9  reviews
    $740 per night
      Book Now
  • Luxuriously Private Tropical 6br/5ba Villa

    Kahala Ali'i - Luxuriously Private Brand new to the luxury vacation rental market, Kahala Ali'i is a large villa completely fenced in with an ...

    • 6 bedroom
    • 5 bathroom
    • Sleeps 14
    HI> Honolulu
    7 night min stay1  reviews
    $1,800 per night
      Book Now
  • Executive Diamond Head Retreat

    This spacious home is located in the exclusive Kahala community. The EXECUTIVE DIAMOND HEAD RETREAT, has everything you need for your vacation! ...

    • 5 bedroom
    • 7 bathroom
    • Sleeps 10
    HI> Honolulu
    14 night min stay3  reviews
    $700 per night
      Book Now
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