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Diamond Head Grand Escape

5 bedrooms·5.5 bathrooms·10 guests·7,324 sq/ft
Beachfront
Pool
Hot tub/Jacuzzi
Pool table

An exceptional beachfront retreat in Honolulu’s exclusive Diamond Head Cove, this award-winning residence redefines luxury island living. With direct access to the sand and panoramic ocean views, the home spans over 7,300 square feet and features five expansive ensuite bedrooms, a floating glass staircase, and refined finishes throughout. Soaring ceilings, a sleek wine closet, and a chef-grade kitchen seamlessly merge with walls of glass that open to the Pacific, blending indoor elegance with outdoor serenity. A private elevator, smart automation, and a state-of-the-art audio system elevate the experience with effortless comfort. Outdoors, an infinity-edge pool and spa create a resort-caliber escape framed by tiki torches and swaying palms. The covered lanai is fully equipped with a kitchen and lounge area, ideal for sunset dining or post-surf relaxation. Whether gathered around the pool or unwinding in the oceanview primary suite with dual bathrooms and a steam shower, every space is curated for beauty and ease. Just minutes from Waikiki’s vibrant energy yet worlds away in feel, this home offers the rarest of opportunities: a modern sanctuary set directly on one of Oʻahu’s most treasured coastlines.

Our promise

Satisfaction Guarantee

We've reviewed thousands of homes and approve only the best. Each one is professionally managed and vetted for comfort and style, raising the bar for every stay.

KEY Curation Notes

One of only 27 properties with direct beachfront access in Diamond Head Cove — and Diamond Head Beach Park is a 1-minute walk. The estate sits on the sand at the foot of the crater, steps from Cromwell's surf break and the Diamond Head State Monument trailhead. The coastal walking path to Kapiolani Park, Waikiki, and the aquarium begins outside the front gate. Diamond Head Market & Grill is 4 minutes by car.
Every bedroom is a king with its own ensuite, and the primary suite has dual bathrooms. Five king suites with private bathrooms throughout. The primary suite includes both his-and-hers bathrooms, a steam shower, ocean and garden views, and a private lanai. An elevator accesses all levels — practical given the 7,324 square feet across multiple floors.
The entertainment infrastructure is genuinely resort-scale. Infinity-edge pool and spa, outdoor kitchen and full bar, game room with billiards, glass-enclosed wine closet, home library, media lounge, whole-home automation, and Sonos audio throughout. Surfboard and outrigger storage sits steps from the water — this is a home built around active ocean use.
Monthly only, currently for sale, and security cameras are present. The full 30-day rate applies regardless of nights used. A marketing disclaimer is provided at booking confirming exclusive occupancy during your rental period. Worth factoring into planning for any group sensitive to the property being actively shown.
KEY.co grocery delivery makes strong sense at this scale. Diamond Head Market & Grill is 4 minutes away for daily provisions, but arriving fully stocked for a month-long stay allows the chef's kitchen and butler's pantry to deliver from the first evening without a grocery run on arrival day.

Amenities

Indoor
Blender
Ceiling fans
Coffee grinder
Coffee maker
Dishes utensils
Outdoor
Garden/Backyard
Pool
Hot tub/Jacuzzi
Balcony
Outdoor dining area
Misc
WiFi
Additional bedding
Beach towels
Essentials
Ethernet connection

Bedroom details

Bedroom 1: King
Bedroom 2: King
Bedroom 3: King
Bedroom 4: King
Bedroom 5: King

Location

Inside the destination

Neighborhood: Diamond Head - Set directly on the sand within the exclusive Cove area of Diamond Head, this home is one of only 27 with private beachfront access; steps to Cromwell’s surf break. - 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.

Parking information

- Parking space provided. - Free parking is available. - Please park in your designated parking areas. Please be respectful of the neighbors and do not block driveways, sidewalks, or mailboxes.

Getting to the property

Car is recommended.

We're here to help

Whether you have questions on this home or want us to source other options, we're a message away!

Policies

Check-in: 4:00 PM
Check-out: 10:00 AM
Renter's age: 21+ years old
Quiet Hours: 8:00 PM - 8:00 AM
No smoking allowed
No events allowed
No pets

Cancellation policy

Plans change, we get it.

Enjoy peace of mind when booking with KEY.co.

90% Refund: Receive a 90% refund when you cancel your reservation at least 46 days before check-in.

50% Refund: Receive a 50% refund when you cancel your reservation at least 31 days before check-in.

No Refund: Reservations canceled 45 days or less before check-in are not eligible for a refund.

Refunds subject to a 5% processing fee of the total.

Things you need to know

24Hr Check-in

Suitable for the elderly.

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.

Hotel-like amenities such as daily cleaning and bell service are not provided. Additional services can be requested with advanced notice at an additional cost.

Guests who are staying for an extended period of time may require one or more mid-stay cleaning services. The frequency of mid-stay cleanings will vary by property and guest preference. If you prefer to have additional cleanings scheduled during your stay, then it should be discussed in advance with your Reservations Manager so that all of the details can be arranged and the cleanings properly scheduled.

Restrictions

Guests & Occupancy

  • Primary renter must be 21+ and must be the same person as the credit/debit cardholder.
  • Limited to two guests per bedroom unless otherwise specified. For tiered-rate properties, occupancy is restricted to the number of guests booked. Full legal names of all occupants are required prior to check-in.
  • Additional guests require prior written approval and are subject to extra nightly fees.
  • For personal vacation use only. No commercial, business, or event use unless pre-approved in writing (additional charges may apply). No subletting.
  • Guest is responsible for all invitees and for any damages, fines, service calls, excessive cleaning, repairs, or assessments caused during occupancy (charged to card on file).
  • Special Resort Terms_ (if applicable – Hualalai)_: Daily resort fees and charges paid directly to resort. Amenities and access subject to change without notice; no refunds for limitations.
  • Resort Amenity Limitations _(if applicable – Hualalai)_: Amenities and access controlled by resort; no guarantees or refunds for restrictions.
  • Optional management coordination services billed at $75/hour with prior agreement.

Events & Noise

  • Parties, weddings, or gatherings exceeding maximum occupancy are prohibited. Violations may result in immediate termination of rental agreement.
  • Any event or non-standard use requires prior written approval and may incur additional fees.
  • Strict Good Neighbor Policy. Excessive noise (indoors or outdoors, including pool/spa, patios, lanais) is prohibited.
  • Guests must comply with posted community quiet hours. Violations may result in eviction without refund.

Prohibited Activities

  • Smoking/Vaping: Strictly prohibited anywhere on property (including lanais and balconies). Guest responsible for all remediation, deodorizing, damage repairs, and potential lost rental income.
  • Illegal Activity: Use of property for illegal or unlawful purposes is prohibited.

Equipment & Amenities

  • Pool & Spa _(if equipped)_: Use at own risk. No unsupervised children. Follow all posted safety rules. No diving in shallow areas. No glass near pool/spa. Comply with posted occupancy and hour restrictions. Pool fences available upon request for an additional fee (must be scheduled in advance). Turn off hot tub heat when not in use.
  • Recreational Equipment _(if equipped)_: Inspect before use; report issues immediately. Use according to laws and safety guidelines. Guest assumes all risk of injury or damage.
  • Utility Usage: Rental includes normal utility usage. Excessive usage will be charged to guest + 4.5% processing fee. Stays over 30 days may have utility caps.
  • Mechanical/Electrical Systems: No guarantees on AC, appliances, internet, TV, water, power, etc. Guests must report issues promptly. Service calls caused by guest misuse will be billed. No rent deductions for failures.
  • Extended outages may occur due to wildfire safety programs or extreme weather.

Checkout & Care

  • Early arrival requires prior approval.
  • Property must be left tidy and in similar condition to arrival.
  • Late departures without approval incur hourly charges (minimum one hour). After 4 pm, fee may equal the full daily rental rate.
  • Excessive cleaning billed at a minimum of $45/hour per cleaner.
  • Guests must report pre-existing damage upon arrival. Failure to report issues during stay may void refund consideration.
  • Guests must immediately report access issues or equipment malfunctions.

Liability & Disclaimers

  • Not liable for injuries or accidents.
  • Not liable for injury or loss. Guest assumes full responsibility.
  • No refunds for weather, hurricanes, road conditions, tsunamis, volcanic activity, pests, beach/ocean conditions, or similar acts of nature. Travel insurance is recommended. If the property becomes uninhabitable and insurance not purchased, rescheduling within one year may be offered.
  • All Hawaii beaches are public and not controlled by management. Lifeguards are not present on many beaches. Ocean conditions (tides, currents, rip tides, sea life, storms) are unpredictable and vary by location and season. Guests use the beaches and ocean at their own risk. No refunds for beach or ocean conditions.
  • No refunds for nearby construction noise.
  • No refunds for failure of utilities, appliances, internet, AC, or similar systems.
  • If property becomes unavailable (sale, law change, safety issue, loss of management), refund limited to payments made.
  • Not responsible for lost, delayed, or undeliverable mail/packages.
  • Hawaii is subject to environmental hazards. Guest responsible for evacuation awareness.