Diamond Head Grand Escape

United States / Hawaii / Oahu

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.

Villa Overview

Up to 10 Guests
Up to 5 Bedrooms
5.5 Bathrooms
from 30 Min. Nights

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
  • TA-085-937-5616-01

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

Features

5 Bedrooms, 5.5 Bathrooms

Sleeps 10 People

Beach Front

Wifi/Internet

Hot Tub

Private Pool

Scuba diving or Snorkeling

Boogie Boards

Spa and wellness

Iron

Dryer

Washer

Hair Dryer

Shampoo

Linens

Extra Pillows And Blankets

Additional Bedding

Oven

Rice Cooker

Freezer

Kettle

Espresso Machine

Ice Machine

Blender

Toaster Oven

Coffee Grinder

Food Processor

Mixer

Stove

Dishes Utensils

Dishwasher

Microwave

Coffee Maker

Refrigerator

Toaster

Dining Area

Kitchen Basics

Outdoor Shower

Parking space

Garden

Private yard

Outdoor Kitchen

Suitable for Elderly

Garage

Ceiling fans

Free Parking

Car Recommended

Smoke Detector

Garden View

Lanai/Balcony

Fire Extinguisher

Stair Gates

Outdoor seating

Wine Fridge

Deadbolt Lock

Keypad

Security Cameras

Private Entrance

Outdoor Lighting

Pool Table

Speaker System

Satellite or Cable TV

Game room

Smart TV

Sonos Audio System

Beach Umbrella

Insulated Cooler Bag

Cooler - Ice Chest

Beach Chairs

Beach Towels

Ethernet Connection

Laptop Friendly

Details

Bedroom Details

Bedroom 1: Master with King bed, primary en-suite including both his and hers bathrooms, steam shower, ocean and garden views, central AC, ceiling fan
Bedroom 2: Guest with King bed, en-suite bathroom, central AC
Bedroom 3 – Guest with King bed, en-suite bathroom, central AC
Bedroom 4 – Guest with King bed, en-suite bathroom, central AC
Bedroom 5 – Guest with King bed, en-suite bathroom, central AC

Bathroom Details

Bedroom 1: Master primary en-suite including both his and hers bathrooms, steam shower
Bedroom 2: Guest en-suite bathroom
Bedroom 3: Guest en-suite bathroom
Bedroom 4: Guest en-suite bathroom
Bedroom 5: Guest en-suite bathroom
Powder Room 1: Half bathroom

Beach Details

Beachfront property
Diamond Head Beach Park: 2 minutes
Kaalawai Beach: 3 minutes

Pool Details

Private Pool
Hot Tub

Location Details

Ala Wai Golf Course: 9 minutes
Roger Dunn Golf Course: 12 minutes
Daniel K. Inouye International Airport: 18 minutes

Villa Notes

Non smoking
Sorry no pets
A car is recommended

Exclusive Offers

Book now and get 5% off regular villa rates for travel March 1 to May 15, 2026.


Valid for new bookings made now to 5/10/26 for travel 3/1/26 to 5/15/26. Subject to availability and may not be combinable with other offers. Additional restrictions may apply; please call for full details.

Tax Service Charge Details*
Please add 18.712% tax to all rates
Service fee: $295
$2,750 Plus tax departure cleaning fee
Mid-stay cleaning after 14 days: $880 Plus tax
2.3% Booking fee
Accidental Damage Waiver
A $299 Accidental Damage Waiver applies to every reservation.
Minimum Stay Details
Minimum night stay may vary by season. Contact a villa specialist to confirm.

Location

Villa information may change without notice and should be confirmed with our villa rental specialists.