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.

List
Map
  • Blue house ocean view (Top floor)4BR/ 2.5 BA/ 2parking

    We have two Apartments. Both are beautiful and spacious with lots of light and ocean breezes. Both were completely remodeled and decorated recently and they provide a comfortable and airy base for a tropical vacation close to the city and resort...
    Registration Number: TA-002-804-3264-01, GE-00

    • 0 bedroom
    • 1 bathroom
    • Sleeps 5
    HI> Honolulu
    30 night min stay2  reviews
    from $220 per night
      Book Now
  • 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-14

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    HI> Honolulu
    30 night min stay1  reviews
    from $750 per night
      Book Now
  • 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: TA-019-756-4416-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    HI> Honolulu
    28 night min stay41  reviews
    from $450 per night
      Book Now
  • Luxe- Beach House Minutes from Waikiki.

    Imagine staying 10 steps from a sandy beach with access to camping, fishing, surfing, and more... Quiet, private, peaceful. Walk along the beach with your morning coffee. Relax to the sound of the waves as you lounge day and night next to the ...
    Registration Number: TA-127-322-3608-01, GE-12

    • 2 bedroom
    • 1 bathroom
    • Sleeps 6
    HI> Honolulu
    2 night min stay3  reviews
    from $1,170 per night
      Book Now
  • Blue house (Main floor) 5 bedrooms 2.5 baths

    Please read all the descriptions. This listing is for the main floor apartment. with 5 bed rooms and 2.5 bathrooms. There is another apartment with 3 and a attic bedrooms and 2.5 bathrooms which is on the top floor and we offer an option so ...
    Registration Number: TA-002-804-3264-01, GE-00

    • 5 bedroom
    • 2 bathroom
    • Sleeps 5
    HI> Honolulu
    30 night min stay3  reviews
    from $220 per night
      Book Now
  • Nicely Remodeled w/ Ocean Views | 1 Block to Beach | Free Parking

    ** PLEASE NOTE: - The tennis court is temporally closed until further notice - POOL CLOSE for Maintenance FROM May 8th to May 18th, 2022 **POOL OPENS May 19th at 8am SPAS CLOSE for Maintenance May 9th to May 27th, 2022 ** SPAS OPEN May 28th ...
    Registration Number: TA-198-263-8592-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 5
    HI> Honolulu
    1 night min stay36  reviews
    from $236 per night
      Book Now
  • Right on the beach near Diamond Head and 4 miles from Waikiki!

    On the beach, in a coveted luxury resort location are the Kahala Beach condos, adjacent to the Kahala Hotel, the only 5-star Hawaiian destination. Secure, with 24/7 guards, keyed building access, and a private underground parking garage. Sited ...
    Registration Number: TA-165-278-3616-01, GE-16

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    HI> Honolulu
    30 night min stay1  reviews
    from $198 per night
      Book Now
  • Deluxe 12th Floor Garden View Condo at Waikiki Banyan by RedAwning

    2 Queen Sized Beds, 1 Bath, Waikiki Banyan, Free WiFi and Parking Enjoy a fully-equipped kitchen and comfortable seating in the living room. Kitchen includes refrigerator, range, microwave, rice maker, coffee maker, and other standard kitchen ...
    Registration Number: TA-121-578-0864-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 6
    HI> Honolulu
    2 night min stay0  reviews
    from $231 per night
      Book Now
  • Waikiki Banyan High Level Condo with Private Lanai by RedAwning

    2 Queen Sized Beds, Waikiki Banyan Condo, Free Parking & WiFi Enjoy a fully-equipped kitchen and comfortable seating in the living room which opens up to your private lanai. Kitchen includes refrigerator, range, microwave, rice maker, coffee ...
    Registration Number: TA-121-578-0864-01

    • 1 bedroom
    • 1 bathroom
    • Sleeps 6
    HI> Honolulu
    2 night min stay0  reviews
    from $219 per night
      Book Now
  • Immaculate Balinese Style Home, near Diamond Head

    Begin your Hawaii vacation by stepping into a Balinese-Style Oasis located just mauka (the mountain side) of Diamond Head and minutes from the beach. This 5 bedroom, 4 bath home combines pleasingly aesthetic features, plentiful space and an ...
    Registration Number: TA-096-950-5280-01, 13205

    • 6 bedroom
    • 4 bathroom
    • Sleeps 13
    HI> Honolulu
    3 night min stay0  reviews
    from $1,314 per night
      Book Now
  • Luxurious Kahala Grand Splendor: Private Home w/Pool, Spa, AC & Lush Landscaping

    Admiration starts at first glance with this contemporary vacation residence, located in a luxury residential area in Kahala, right at the slopes of Diamond Head. The luxury residence was completed in 2015, boasting a huge pool, luxurious rooms ...
    Registration Number: TA-139-412-1216-01, GE-13

    • 5 bedroom
    • 5 bathroom
    • Sleeps 10
    HI> Honolulu
    7 night min stay0  reviews
    from $4,000 per night
      Book Now
  • 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-04

    • 3 bedroom
    • 2 bathroom
    • Sleeps 4
    HI> Honolulu
    30 night min stay0  reviews
    from $198 per night
      Book Now
  • Home in the Sky!

    Stunning brand new home with 3 bedrooms and 3 full bathrooms with beautiful views and absolute serenity. All new stainless appliances & new furniture, beautiful kitchen with granite and spectacular view and WIFI.! Wake up to the best sunrise on...
    Registration Number: TA-048-102-1952-01, GE-04

    • 3 bedroom
    • 3 bathroom
    • Sleeps 3
    HI> Honolulu
    30 night min stay0  reviews
    from $218 per night
      Book Now
  • Cozy 3BD, 2BA fully furnished with beautiful mountain views.

    Nestled in beautiful Palolo valley just inland from Diamond Head, Honolulu, our family and PET-friendly fully furnished home is a spacious 3 bedroom retreat with mountain views near fantastic hiking trails, parks, beaches, surfing spots, and ...
    Registration Number: TA-155-402-0864-01, GE-15

    • 3 bedroom
    • 2 bathroom
    • Sleeps 4
    HI> Honolulu
    30 night min stay0  reviews
    from $133 per night
      Book Now