Diamond Head Grand Escape

Honolulu, HI 5 Bedrooms Vacation Rental

5 Beds 5 Baths Sleeps 10
Step onto your lanai to take in uninterrupted ocean vistas, the perfect spot for coffee or cocktails. Enjoy seamless indoor-outdoor living with the infinity pool just steps from the great room.
Enjoy seamless indoor-outdoor living with the infinity pool just steps from the great room.

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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 King

5 Beds 5 Baths Sleeps 10

Amenities

Private pool
Air conditioning
Beach Front
Hot Tub

Description

This award-winning oceanfront residence, Diamond Head Grand Escape, offers a rare opportunity to experience contemporary Hawaiian living in one of Honolulu’s most coveted enclaves. Set directly on the sand within the exclusive Cove area of Diamond Head, this home is one of only 27 with private beachfront access. With 7,324 square feet of refined interiors, five ensuite bedrooms, and spectacular outdoor spaces, it is perfectly curated for families, friends, and guests seeking a true sense of place.

What You’ll Love About Diamond Head Grand Escape
• Direct beachfront location in Diamond Head Cove, steps to Cromwell’s surf break
• Infinity-edge pool and spa with tiki torch ambiance
• Dramatic floating glass staircase and modern wine closet
• State-of-the-art automation, elevator, and whole-home audio
• Outdoor lounge with full kitchen, professional landscaping, and surfboard storage
• Primary bedroom features an ensuite with both his and hers bathrooms

Living & Dining
Walls of glass frame sweeping Pacific views, filling the great room with natural light. Elegant design elements include a floating staircase with glass railings, soaring ceilings, and handcrafted finishes. Multiple seating areas invite conversation and relaxation, while the dining space connects seamlessly with both the chef’s kitchen and lanai for effortless indoor-outdoor flow.

Chef-Ready Kitchen
The gourmet kitchen is outfitted with professional-grade appliances, marble island countertops, and custom cabinetry. A butler’s pantry provides additional storage and prep space, ideal for private chefs or group entertaining.

Outdoor Oasis
Step outside to an infinity-edge pool and spa framed by tiki torches, swaying palms, and the sound of waves. The outdoor lounge features a full kitchen, dining space, and comfortable seating designed for gatherings. Professional landscaping enhances privacy, while direct access to the sand makes the ocean your backyard.

Sleeping Quarters
• Primary Suite – King bed, primary ensuite including both his & hers bathrooms, steam shower, ocean & garden views, central AC, ceiling fan
• Guest Suite 2 – King bed, ensuite bath, central AC
• Guest Suite 3 – King bed, ensuite bath, central AC
• Guest Suite 4 – King bed, ensuite bath, central AC
• Guest Suite 5 – King bed, ensuite bath, central AC
• Powder Room – Half bath

Extras
A glass-enclosed wine closet, home office, library, and game room provide versatility for work and play. The residence also includes whole-home automation, a security system, elevator, and audio throughout. Surfboard and outrigger storage are conveniently located steps from the sand.

Nearby
Walk to Waikiki’s vibrant dining and nightlife or hike the iconic Diamond Head crater. The surf break at Cromwell’s is just offshore, while a short drive brings you to Ala Moana shopping, cultural venues, and championship golf.

Good to Know
This home is available exclusively for 30-day minimum stays. The property is also currently for sale; a marketing disclaimer will be provided at booking. Occupancy is exclusive for your rental period. TAT and applicable taxes apply.

TMK: 310390060000
TAT:

Reserve your dates now at Diamond Head Grand Escape and experience an oceanfront lifestyle defined by elegance, comfort, and design.

Room

Beds


Primary Bedroom

King (1)

Ensuite Bathroom, Ocean View, Garden View, Central AC, Ceiling Fan


Guest Bedroom 2

King (1)

Ensuite Bathroom, Central AC


Guest Bedroom 3

King (1)

Ensuite Bathroom, Central AC


Guest Bedroom 4

King (1)

Ensuite Bathroom, Central AC


Guest Bedroom 5

King (1)

Ensuite Bathroom, Central AC


Primary Bedroom Ensuite

full bathroom


Guest Full Bathroom 2

full bathroom


Guest Full Bathroom 3

full bathroom


Guest Full Bathroom 4

full bathroom


Guest Full Bathroom 5

full bathroom


Powder Room 1

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 Grinder
  • Coffee Maker
  • Dining Area
  • Dishes Utensils
  • Dishwasher
  • Disposal
  • Espresso Machine
  • Food Processor
  • Freezer
  • Ice Machine
  • Kettle
  • Kitchen
  • Kitchen Basics
  • Microwave
  • Mixer
  • Oven
  • Refrigerator
  • Rice Cooker
  • Stove
  • Toaster
  • Toaster Oven
  • Wine Fridge

Amenities

  • Dryer
  • Essentials
  • Ethernet Connection
  • Extra Pillows And Blankets
  • Garage
  • Hair Dryer
  • Iron
  • Keypad
  • Linens
  • Parking space
  • Private Entrance
  • Shampoo
  • Washer
  • Wifi/Internet

Suitability

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

Emergency

  • Emergency Fire Contact
  • Emergency Police Contact

Cleanliness

  • 24Hr Check-In

Safety Features

  • Deadbolt Lock
  • Fire Extinguisher
  • Outdoor Lighting
  • Security Cameras
  • Smoke Detector

Entertainment

  • Game room
  • Laptop Friendly
  • Pool Table
  • Satellite or Cable TV
  • Smart TV
  • Sonos Audio System
  • Speaker System
  • Television

Pool/Spa

  • Heated Pool
  • Hot Tub
  • Private Pool

Internal Amenities

  • Additional Bedding
  • Beach Chairs
  • Beach Towels
  • Boogie Boards
  • Stair Gates

Outdoor Amenities

  • Beach Umbrella
  • Cooler - Ice Chest
  • Garden
  • Insulated Cooler Bag
  • Lanai/Balcony
  • Outdoor Kitchen
  • Outdoor Shower
  • Outdoor seating
  • Private yard

Themes

  • Family
  • Luxury
  • Romantic

Car

  • Car Recommended

Location/Property Types

  • Beach Front
  • Garden View
  • Ocean Front
  • Popular Town
  • Private / Secluded
  • Walk to Shops / Restaurants
  • Waterfront

Property Manager

  • Claudia Evenschor

Promos

  • Holidays

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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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