Diamond Head Grandeur

Diamond Head Grandeur

Diamond Head, Oahu, Hawaii
  • 5 beds
  • 5 baths
  • Sleeps 10

Overview

Welcome to Diamond Head Grandeur, a breathtaking 5 bedroom, 5.5 bathroom luxury villa located in the prestigious Kahala neighborhood on Oahu’s south shore. Just minutes from the iconic Diamond Head State Monument, Kaalawai Beach, and the vibrant energy of Waikiki and Honolulu, this 5,727 square foot estate blends contemporary design, indoor outdoor elegance, and lush tropical surroundings. With panoramic ocean views, a cascading infinity pool, jacuzzi spa, and refined interiors across three levels, this exceptional home offers an unforgettable retreat for up to 10 guests.

Property Highlights

  • Unparalleled location near Kaalawai Beach, Diamond Head, Waikiki, and Kahala
  • Stunning outdoor living with cascading infinity pool, jacuzzi spa, lounge seating, and ocean views
  • Three floors of luxurious living with an elevator for easy access
  • Five spacious ensuite bedrooms with central AC
  • Sleek, modern interiors with high ceilings and natural light
  • Lower level media room with lounge seating, large TV, and ping pong table
Welcome to Diamond Head Grandeur, a breathtaking 5 bedroom, 5.5 bathroom luxury villa located in the prestigious Kahala neighborhood on Oahu’s south shore. Just minutes from the iconic Diamond Head State Monument, Kaalawai Beach, and the vibrant energy of Waikiki and Honolulu, this 5,727 square foot estate blends contemporary design, indoor outdoor elegance, and lush tropical surroundings. With panoramic ocean views, a cascading infinity pool, jacuzzi spa, and refined interiors across three levels, this exceptional home offers an unforgettable retreat for up to 10 guests. What You’ll Love About Diamond Head Grandeur • Unparalleled location near Kaalawai Beach, Diamond Head, Waikiki, and Kahala • Stunning outdoor living with cascading infinity pool, jacuzzi spa, lounge seating, and ocean views • Three floors of luxurious living with an elevator for easy access • Five spacious ensuite bedrooms with central AC • Sleek, modern interiors with high ceilings and natural light • Lower level media room with lounge seating, large TV, and ping pong table Living and Dining The main level offers an expansive open concept living area featuring a large sectional sofa, armchairs, and a 55 inch flat screen TV. Floor to ceiling sliding glass doors open onto the covered lanai, creating a seamless indoor outdoor living experience. The dining area seats eight comfortably, making it ideal for gatherings or casual meals after a day exploring Oahu. Chef Ready Kitchen The gourmet kitchen is equipped with modern stainless steel appliances, a large island with bar seating, sleek cabinetry, and everything needed for cooking or entertaining. Whether preparing an elaborate meal or enjoying morning coffee, this kitchen makes hosting effortless. Outdoor Oasis The villa’s outdoor retreat is designed for total relaxation. Enjoy the cascading infinity pool, jacuzzi spa, lounge seating, BBQ grill, and covered outdoor dining area. Tropical landscaping and ocean views create the perfect backdrop for sunbathing, swimming, or sunset dinners. Sleeping Quarters • Primary Suite – King bed, upper level, private lanai with panoramic ocean views, ensuite bath with walk in shower, dual vanities, and soaking tub • Guest Suite 2 – King bed, lower level, ensuite bath, central AC • Guest Suite 3 – King bed, main level, ensuite bath, central AC • Guest Suite 4 – King bed, upper level, ensuite bath, central AC • Guest Suite 5 – Queen bed, upper level, ensuite bath, central AC • Half Bath – Located on main level Lower Level Media Room The lower floor features a comfortable entertainment room with lounge seating, a large flatscreen TV, and a ping pong table, offering a perfect setting for movie nights or friendly competitions. Extras • Elevator to all three floors • Sonos audio system • Beach chairs, towels, boogie boards, and cooler • Outdoor shower • Private two car garage • Full laundry room • Additional bedding and essentials Nearby • Walk: Kaalawai Beach, Scenic shoreline paths, Diamond Head foothill area • Short Drive: Waikiki Beach, dining, shopping, and nightlife, Kahala Mall and Whole Foods, Honolulu Zoo and Kapiolani Park, Waialae Country Club, Hanauma Bay Nature Preserve, Kahala Hilton Hotel for dining and dolphin shows, Hawaii Kai dining, marina activities, and Costco Good to Know • Minimum 30 night rental required per Honolulu zoning laws • Full 30 day rate applies regardless of number of nights occupied • Property is exclusively available to renter for the entire rental period • No smoking permitted anywhere on property • Pets not allowed • Elevator available • Tax ID: TA-076-121-8560-01 • TMK: 310400040001 Reserve this extraordinary Kahala home and experience refined island living at Diamond Head Grandeur.

RoomsOccupancy

  • Primary Bedroom

    Upper Level, Ensuite Bathroom, Ocean View, Central AC

    • King (1)

  • Guest Bedroom 2

    Lower Level, Ensuite Bathroom, Central AC

    • King (1)

  • Guest Bedroom 3

    Main / Center Level, Ensuite Bathroom, Central AC

    • King (1)

  • Guest Bedroom 4

    Upper Level, Ensuite Bathroom, Central AC

    • King (1)

  • Guest Bedroom 5

    Upper Level, Ensuite Bathroom, Central AC

    • Queen (1)

  • Primary Bedroom Ensuite

    • Guest Bedroom 2 Ensuite

      • Guest Bedroom 3 Ensuite

        • Guest Bedroom 4 Ensuite

          • Guest Bedroom 5 Ensuite

            • Half Bath

              Nearby Activities

              • Spa and wellness
              • Zoo
              • Museums
              • Hiking
              • Fishing
              • Watersports
              • Cycling
              • Tennis
              • Scuba diving or Snorkeling
              • Shopping
              • Horseback riding
              • Golfing

              Kitchen and Dining

              • Dining Area
              • Kitchen Basics
              • Kitchen
              • Refrigerator
              • Coffee Maker
              • Microwave
              • Dishwasher
              • Dishes Utensils
              • Stove
              • Toaster
              • Oven
              • BBQ
              • Freezer
              • Kettle
              • Ice Machine
              • Blender
              • Toaster Oven
              • Rice Cooker
              • Food Processor
              • Disposal

              Amenities

              • Essentials
              • Shampoo
              • Dryer
              • Washer
              • Garage
              • Hair Dryer
              • Linens
              • Iron
              • Parking space
              • Safe
              • Keypad
              • Wifi/Internet
              • Private Entrance

              Cleanliness

              • Self Check In / Check Out

              Suitability

              • Children Welcome
              • Smoking Not Allowed
              • Air Conditioning
              • Bath Tub
              • Hot Water
              • Free Parking

              Entertainment

              • Television
              • Stereo
              • Satellite or Cable TV
              • I-Pod Station / Bluetooth Speaker
              • Sonos Audio System

              Pool/Spa

              • Hot Tub
              • Private Pool

              Internal Amenities

              • Beach Towels
              • Beach Chairs
              • Shipping Items
              • Boogie Boards
              • Additional Bedding
              • Recent Property Upgrades

              Outdoor Amenities

              • Cooler - Ice Chest
              • Beach Umbrella
              • Outdoor Shower
              • Garden
              • Private yard
              • Beach Equipment Rentals Available ($)
              • Lanai/Balcony

              Car

              • Car Recommended

              Property Manager

              • Claudia Evenschor
              • 30 Day Properties

              Promos

              • Holidays

              September 2026

              SMTWTFS
              04$1,60005$1,600
              06$1,60007$1,60008$1,60009$1,60010$1,60011$1,60012$1,600
              13$1,60014$1,60015$1,60016$1,60017$1,60018$1,60019$1,600
              20$1,60021$1,60022$1,60023$1,60024$1,60025$1,60026$1,600
              27$1,60028$1,60029$1,60030$1,600

              October 2026

              SMTWTFS
              01$1,56102$1,56103$1,561
              04$1,56105$1,56106$1,56107$1,56108$1,56109$1,56110$1,561
              11$1,56112$1,56113$1,56114$1,56115$1,56116$1,56117$1,561
              18$1,56119$1,56120$1,56121$1,56122$1,56123$1,56124$1,561
              25$1,56126$1,56127$1,56128$1,56129$1,56130$1,56131$1,561

              November 2026

              SMTWTFS
              01$1,56102$1,56103$1,56104$1,56105$1,56106$1,56107$1,561
              08$1,56109$1,56110$1,56111$1,56112$1,56113$1,56114$1,561
              15$1,56116$1,79417$1,79418$1,79419$1,79420$1,79421$1,794
              22$1,79423$1,79424$1,79425$1,79426$1,79427$1,79428$1,794
              29$1,79430$1,794

              December 2026

              SMTWTFS
              01$2,20002$2,20003$2,20004$2,20005$2,200
              06$2,20007$2,20008$2,20009$2,20010$2,20011$2,20012$2,200
              13$2,20014$2,20015$2,20016$2,20017$2,20018$2,20019$2,200
              20$2,20021$2,20022$2,20023$2,20024$2,20025$2,20026$2,200
              27$2,20028$2,20029$2,20030$2,20031$2,200

              January 2027

              SMTWTFS
              01$2,20002$2,200
              03$2,20004$2,20005$2,20006$2,20007$2,20008$2,20009$2,200
              10$2,20011$2,20012$2,20013$2,20014$2,20015$1,60016$1,600
              17$1,60018$1,60019$1,60020$1,60021$1,60022$1,60023$1,600
              24$1,60025$1,60026$1,60027$1,60028$1,60029$1,60030$1,600
              31$1,600

              February 2027

              SMTWTFS
              01$1,60002$1,60003$1,60004$1,60005$1,60006$1,600
              07$1,60008$1,60009$1,60010$1,60011$1,60012$1,60013$1,600
              14$1,60015$1,60016$1,60017$1,60018$1,60019$1,60020$1,600
              21$1,60022$1,60023$1,60024$1,60025$1,60026$1,60027$1,600
              28$1,600

              March 2027

              SMTWTFS
              01$1,60002$1,60003$1,60004$1,60005$1,60006$1,600
              07$1,60008$1,60009$1,60010$1,60011$1,60012$1,60013$1,600
              14$1,60015$1,60016$1,60017$1,60018$1,60019$1,60020$1,600
              21$1,60022$1,60023$1,60024$1,60025$1,60026$1,60027$1,600
              28$1,60029$1,60030$1,60031$1,600

              April 2027

              SMTWTFS
              01$1,60002$1,60003$1,600
              04$1,60005$1,60006$1,60007$1,60008$1,60009$1,60010$1,600
              11$1,60012$1,60013$1,60014$1,60015$1,60016$1,60017$1,600
              18$1,60019$1,60020$1,60021$1,60022$1,60023$1,60024$1,600
              25$1,60026$1,60027$1,60028$1,60029$1,60030$1,600

              May 2027

              SMTWTFS
              01$1,600
              02$1,60003$1,60004$1,60005$1,60006$1,60007$1,60008$1,600
              09$1,60010$1,60011$1,60012$1,60013$1,60014$1,60015$1,600
              16$1,60017$1,60018$1,60019$1,60020$1,60021$1,60022$1,600
              23$1,60024$1,60025$1,60026$1,60027$1,60028$1,60029$1,600
              30$1,60031$1,600

              June 2027

              SMTWTFS
              01$1,60002$1,60003$1,60004$1,60005$1,600
              06$1,60007$1,60008$1,60009$1,60010$1,60011$1,60012$1,600
              13$1,60014$1,60015$1,60016$1,60017$1,60018$1,60019$1,600
              20$1,60021$1,60022$1,60023$1,60024$1,60025$1,60026$1,600
              27$1,60028$1,60029$1,60030$1,600

              July 2027

              SMTWTFS
              01$1,60002$1,60003$1,600
              04$1,60005$1,60006$1,60007$1,60008$1,60009$1,60010$1,600
              11$1,60012$1,60013$1,60014$1,60015$1,60016$1,60017$1,600
              18$1,60019$1,60020$1,60021$1,60022$1,60023$1,60024$1,600
              25$1,60026$1,60027$1,80028$1,80029$1,80030$1,80031$1,800

              August 2027

              SMTWTFS
              01$1,80002$1,80003$1,80004$1,80005$1,80006$1,80007$1,800
              08$1,80009$1,80010$1,80011$1,80012$1,80013$1,80014$1,800
              15$1,80016$1,80017$1,80018$1,80019$1,80020$1,80021$1,800
              22$1,80023$1,80024$1,80025$1,80026$1,80027$1,80028$1,800
              29$1,80030$1,80031$1,800

              September 2027

              SMTWTFS
              01$1,60002$1,60003$1,60004$1,600
              05$1,60006$1,60007$1,60008$1,60009$1,60010$1,60011$1,600
              12$1,60013$1,60014$1,60015$1,60016$1,60017$1,60018$1,600
              19$1,60020$1,60021$1,60022$1,60023$1,60024$1,60025$1,600
              26$1,60027$1,60028$1,60029$1,60030$1,600

              October 2027

              SMTWTFS
              01$1,70002$1,700
              03$1,70004$1,70005$1,70006$1,70007$1,70008$1,70009$1,700
              10$1,70011$1,70012$1,70013$1,70014$1,70015$1,70016$1,700
              17$1,70018$1,70019$1,70020$1,70021$1,70022$1,70023$1,700
              24$1,70025$1,70026$1,70027$1,70028$1,70029$1,70030$1,700
              31$1,700

              November 2027

              SMTWTFS
              01$1,70002$1,70003$1,70004$1,70005$1,70006$1,700
              07$1,70008$1,70009$1,70010$1,70011$1,70012$1,70013$1,700
              14$1,70015$1,70016$1,80017$1,80018$1,80019$1,80020$1,800
              21$1,80022$1,80023$1,80024$1,80025$1,80026$1,80027$1,800
              28$1,80029$1,80030$1,800

              December 2027

              SMTWTFS
              01$1,80002$1,80003$1,80004$1,800
              05$1,80006$1,80007$1,80008$1,80009$1,80010$1,80011$1,800
              12$1,80013$1,80014$1,80015$1,80016$2,20017$2,20018$2,200
              19$2,20020$2,20021$2,20022$2,20023$2,20024$2,20025$2,200
              26$2,20027$2,20028$2,20029$2,20030$2,20031$2,200

              January 2028

              SMTWTFS
              01$2,200
              02$2,20003$2,20004$2,20005$2,20006$2,20007$2,20008$2,200
              09$2,20010$2,20011$2,20012$2,20013$2,20014$2,20015$2,200
              16$1,70017$1,70018$1,70019$1,70020$1,70021$1,70022$1,700
              23$1,70024$1,70025$1,70026$1,70027$1,70028$1,700
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