Diamond Head Grandeur

Honolulu, Hawaii 5 Bedrooms Vacation Rental

5 Beds 5 Full Baths, and 1 Half Bath Sleeps 10
From the Primary Bedroom, step outside on your own private balcony to take in the gorgeous views The kitchen overlooks the living area, allowing for easy conversation while preparing meals in your Hawaii vacation retreat.
The kitchen overlooks the living area, allowing for easy conversation while preparing meals in your Hawaii vacation retreat.

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Rooms

  • bed icon

    Bedroom # 1

    Primary Bedroom

    1 King

  • bed icon

    Bedroom # 2

    Guest Bedroom 2

    1 King

  • bed icon

    Bedroom # 3

    Guest Bedroom 3

    1 King

  • bed icon

    Bedroom # 4

    Guest Bedroom 4

    1 King

  • bed icon

    Bedroom # 5

    Guest Bedroom 5

    1 Queen

5 Beds 5 Baths Sleeps 10

Amenities

Private pool
Air conditioning
Mountain View
Ocean View

Description

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.

Room

Beds

Primary Bedroom

King (1)

Upper Level, Ensuite Bathroom, Ocean View, Central AC

Guest Bedroom 2

King (1)

Lower Level, Ensuite Bathroom, Central AC

Guest Bedroom 3

King (1)

Main / Center Level, Ensuite Bathroom, Central AC

Guest Bedroom 4

King (1)

Upper Level, Ensuite Bathroom, Central AC

Guest Bedroom 5

Queen (1)

Upper Level, Ensuite Bathroom, Central AC

Primary Bedroom Ensuite

full bathroom

Guest Bedroom 2 Ensuite

full bathroom

Guest Bedroom 3 Ensuite

full bathroom

Guest Bedroom 4 Ensuite

full bathroom

Guest Bedroom 5 Ensuite

full bathroom

Half Bath

half bathroom

Nearby Activities

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

Kitchen and Dining

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

Amenities

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

Cleanliness

  • Self Check In / Check Out

Suitability

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

Entertainment

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

Pool/Spa

  • Hot Tub
  • Private Pool

Internal Amenities

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

Outdoor Amenities

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

Themes

  • Family
  • Luxury

Car

  • Car Recommended

Location/Property Types

  • Garden View
  • Mountain View
  • Ocean View
  • Ocean View (Partial)
  • Walk to Shops / Restaurants
  • Walk to beach

Property Manager

  • 30 Day Properties
  • Claudia Evenschor
  • Mark LeRoy Hualalai

Promos

  • Holidays

promo

  • 2025BF25
  • 2025Cyber
  • 2026Spring15
  • 20Holiday25
  • BDD2026
  • EarlyBF2025

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February 2026

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January 2027

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    Available     Unavailable  Check-In Only  Check-Out Only

Adults

Ages 18 or above

Children

Ages 2-17

Infants

Under 2

Pets

Bringing your pets?

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