Diamond Head Luxe - Image 1
Diamond Head Luxe - Image 2
Diamond Head Luxe - Image 60
1/60

Diamond Head Luxe

5 bedrooms·4.5 bathrooms·11 guests
Beach access
Pool

Situated at the end of a private road in Honolulu's prestigious Diamond Head neighborhood, this exceptional estate offers a luxurious setting for extended island living. Designed with spacious interiors and seamless indoor-outdoor flow, the multi-level residence welcomes natural trade winds through expansive accordion doors that connect the open living areas to a resort-style outdoor retreat. A private swimming pool, covered lanai, and second-story balcony with tranquil ocean views create inviting spaces to relax, while multiple ensuite bedrooms, a separate pool house, and a media room provide comfort and flexibility for families and groups. Every detail has been thoughtfully curated to deliver a refined yet relaxed Hawaiian lifestyle. Just a short walk from the beach and minutes from Diamond Head, Waikīkī, Kahala, and some of Oʻahu's most iconic attractions, the home places the best of the island within easy reach. Spend the day exploring scenic coastal paths, snorkeling in crystal-clear waters, or discovering nearby cafés, shopping, and dining before returning to unwind in the privacy of this peaceful retreat. Complete with a well-appointed kitchen, high-speed Wi-Fi, air-conditioned bedrooms and media room, and generous indoor and outdoor gathering spaces, this residence offers an unforgettable blend of comfort, convenience, and island luxury.

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

Diamond Head Beach Park is a 1-minute walk, with the Diamond Head State Monument trailhead 5 minutes on foot. The estate sits at the end of a private road on Kaalawai Beach, one of the quieter stretches of Honolulu's South Shore coastline. Waikiki dining is about 10 minutes by car; Diamond Head Market & Grill is 4 minutes; Kahala Beach is a 2-minute drive.
The main living areas have no A/C — the home relies on trade wind ventilation. Split A/C units are in all five bedrooms and the media room, but the kitchen, dining room, and main living spaces are open-air by design. This works beautifully in Honolulu's trade wind climate for most of the year — worth noting for groups visiting in summer or who prefer fully climate-controlled common spaces.
Every bedroom has an ensuite, but Suites 4 and 5 share a Jack-and-Jill bathroom. The three king suites each have independent private bathrooms. The queen suite and the two-queen suite share one bathroom between them via a connecting door. The detached pool house suite has its own private entrance, kitchenette, and ensuite — ideal for guests wanting full separation from the main house.
The private pool is the centerpiece of the outdoor space. A covered lanai with lounge seating surrounds the pool, with an outdoor shower and multiple powder rooms adding practical convenience. A second-story balcony provides partial ocean views for quieter morning and evening moments.
Monthly only, with a media room and sofa bed as additional sleeping. The full monthly rate applies regardless of nights used. The media room — with split A/C, kitchenette, sofa bed, and a half bath steps away — accommodates an 11th guest comfortably. KEY.co grocery delivery is a natural fit here; Diamond Head Market & Grill is 4 minutes away, and arriving fully stocked allows the well-equipped kitchen to deliver from the first evening.

Amenities

Indoor
TV
Microwave
Internet
Dryer
Washer
Outdoor
Pool
Garden/Backyard
Beach chairs
Lanai/Balcony
Outdoor shower
Misc
WiFi
Additional bedding
Beach towels
Carbon monoxide detector
Essentials

Bedroom details

Bedroom 1: King
Bedroom 2: King
Bedroom 3 - Pool House: King
Bedroom 4: Queen
Bedroom 5: Two Queens
Media Room: Sleeper Sofa

Location

Inside the destination

Neighborhood: Diamond Head - Nestled at the end of a private road, beach access is a quick one-minute walk away. - Located near Diamond Head, guests are a short drive from Waikiki, Kahala, and some of O'ahu’s most loved beaches. Enjoy easy access to coastal walking paths, local cafés, dining, and world-class snorkeling. Daniel K. Inouye International Airport (HNL) is within convenient reach.

Parking information

- Private driveway parking. - 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
Pets allowed by request

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

Self Check-in / Check-out

Long-term stays allowed.

Suitable for the elderly.

This property is offered as a monthly rental only.

Monthly rate applies in full regardless of the number of nights stayed.

Split A/C is available in all bedrooms and the media room. The kitchen, dining area, and main living spaces are not air-conditioned and rely on natural trade winds and island breezes.

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.