Diamond Head Hawaii Vacation Rentals and Vacation Homes

 41 Rentals in Diamond Head

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Property 85291

Oceanside Elegance

  • "Oceanside Elegance" is a spectacular 7 bedroom, majestic, oceanfront retreat.
  • House in Diamond Head (Near Waikiki)
  • 7 Bedroom(s), Sleeps 14
  • 5 Bathroom(s)
Property 46090

Ali'i Beach Estate

  • This "One-of-a-Kind" South Shore Estate sits on 2.6 acres of lush vegetation and boasts over 350 feet of unobstructed ocean frontage.
  • House in Honolulu (Near Diamond Head)
  • 6 Bedroom(s), Sleeps 16
  • 5 Bathroom(s)
Property 33082

Banyan Tree Beach Estate

  • Banyan Tree Beach Estate Beach Rental - Oahu Hawaii
  • House in Portlock (Near Diamond Head)
  • 5 Bedroom(s), Sleeps 14
  • 5.5 Bathroom(s)
  • Weekly Rates from $6,650 - $10,500
Property 85276

Kailua Plantation Estate

  • The Kailua Plantation Estate is a rare jewel that comes fully appointed with Plantation style finishes and furnishings from around the world.
  • House in Diamond Head (Near Honolulu)
  • 5 Bedroom(s), Sleeps 10
  • 5 Bathroom(s)
Property 85367

Kahala Estate

  • "Kahala Estate" is a magnificent residence that boasts beautiful views of Kahala Beach Park
  • House in Diamond Head (Near Honolulu)
  • 5 Bedroom(s), Sleeps 12
  • 5 Bathroom(s)
  • Retreat to this tropical paradise at this beautiful marina front home.
  • House in Honolulu (Near Diamond Head)
  • 5 Bedroom(s), Sleeps 10
  • 4 Bathroom(s)
Property 13445

A1. The Resort

  • Luxurious home built to the finest of standards and set directly oceanfront in one of Hawaii's most sought after locations.
  • House in Honolulu (Near Diamond Head)
  • 4 Bedroom(s), Sleeps 10
  • 5 Bathroom(s)
Property 46091

Bali Luxury Estate

  • Discover this architectural masterpiece nested in a private street on the slope of the Diamond Head Crater.
  • House in Diamond Head (Near Honolulu)
  • 4 Bedroom(s), Sleeps 8
  • 4 Bathroom(s)
Property 46140

Tropical Oaisis

  • KAHALA VACATION HOME--A retreat the whole family can enjoy
  • House in Kahala (Near Diamond Head)
  • 4 Bedroom(s), Sleeps 8
  • 4.5 Bathroom(s)
  • Weekly Rates from $10,500 - $10,500
Property 26585

Diamond Head Tiki Estate

  • Oceanfront Diamond Head Tiki Estate - Oahu
  • House in Diamond Head
  • 3 Bedroom(s), Sleeps 8
  • 3.5 Bathroom(s)
  • Weekly Rates from $9,000 - $1,200
Property 46092

Bali Estate

  • Sumptuous Balinese Palace with Amazing Ocean Views Peerless Luxury at this Dream Hawaii Getaway
  • House in Diamond Head
  • 3 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)
Property 46094

Black Point Villa

  • Black Point is a gated community on the South Shore of Oahu. It sits on a Black Lava finger surrounded by the Blue Pacific Ocean.
  • Villa in Diamond Head (Near Kahala)
  • 3 Bedroom(s), Sleeps 5
  • 3 Bathroom(s)
  • Weekly Rates from $8,750 - $12,250
  • Diamond Head Seaside Vacation Home - Balinese Inspiration meets European Luxury
  • House in Diamond Head (Near Kahala)
  • 3 Bedroom(s), Sleeps 8
  • 3.5 Bathroom(s)
  • Weekly Rates from $12,250 - $17,500
Property 46097

Gold Coast Ohana Estate

  • The Gold Coast Ohana Estate is located on a magical site, filled with a rich Hawaiian History.
  • House in Diamond Head (Near Waikiki)
  • 3 Bedroom(s), Sleeps 6
  • 2.5 Bathroom(s)
Property 46101

Vintage Hawaiian Estate

  • Retreat into this Vintage 1930s hideaway that graces the enchanting upscale neighborhood of Black Point
  • House in Diamond Head (Near Waikiki)
  • 3 Bedroom(s), Sleeps 6
  • 3 Bathroom(s)
  • Weekly Rates from $10,500 - $12,950
Property 85399

Beachfront Elegance

  • "Beachfront Elegance" is a striking, mid-century, 3 bedroom, 3 bath, walled and gated beachfront property.
  • House in Diamond Head
  • 3 Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
Property 20625

Hibiscus Suite

  • Diamond Head Beach Hotel - Exclusive HIBISCUS SUITE
  • Condo in Diamond Head
  • 2 Bedroom(s), Sleeps 5
  • 1 Bathroom(s)
  • Weekly Rates from $1,800 - $2,500
Property 26624

Executive Elegance

  • Landmark Waikiki - Executive Elegance - Oahu Vacation Condo
  • Condo in Waikiki (Near Diamond Head)
  • 2 Bedroom(s), Sleeps 2
  • 2 Bathroom(s)
Property 33097

Oahu Suite

  • This luxury ocean front 2 bedroom condominium is just what you have been looking for!
  • Condo in Diamond Head
  • 2 Bedroom(s), Sleeps 4
  • 1 Bathroom(s)
  • Weekly Rates from $1,800 - $2,500
Property 46102

Honolulu Suite

  • This family friendly two bedroom oceanfront suite provides comfort, views, a tropical interior that will make you want to come back year after year.
  • Condo in Honolulu (Near Diamond Head)
  • 2 Bedroom(s), Sleeps 5
  • 1 Bathroom(s)
  • Weekly Rates from $1,800 - $2,500
Property 14179

Makapuu Suite

  • Makapu'u Suite - Diamond Head Beach Hotel and Residences on the Gold Coast
  • Condo in Diamond Head (Near Waikiki)
  • 1 Bedroom(s), Sleeps 4
  • 1 Bathroom(s)
  • Weekly Rates from $1,500 - $1,925
Property 26622

Lilikoi Lanai

  • Diamond Head Beach Hotel 11th Floor Condo - Incredible Views!
  • Condo in Diamond Head (Near Honolulu)
  • 1 Bedroom(s), Sleeps 3
  • 1 Bathroom(s)
Property 26629

Tiare Suite

  • Diamond Head Beach Hotel and Residence - The Tiare Suite
  • Condo in Diamond Head (Near Waikiki)
  • 1 Bedroom(s), Sleeps 4
  • 1 Bathroom(s)
  • Weekly Rates from $1,400 - $2,000
Property 26630

Nani Luna Suite

  • Nani Luna Suite - One of a Kind Beachfront Oasis - Diamond Head
  • Condo in Diamond Head
  • 1 Bedroom(s), Sleeps 2
  • 1 Bathroom(s)
  • Weekly Rates from $1,400 - $1,900
Property 26633

Pikake Suite

  • Diamond Head Beach Condo with Forever Views - Oahu
  • Condo in Diamond Head (Near Waikiki)
  • 1 Bedroom(s), Sleeps 3
  • 1 Bathroom(s)


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