Diamond Head Grandeur

United States / Hawaii / Oahu

Welcome to Diamond Head Grandeur, a luxurious 5-bedroom, 5.5-bathroom villa nestled in the prestigious Kahala neighborhood on Oahu’s south shore.

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

Overview

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Just minutes from the iconic Diamond Head State Monument and a short drive from the vibrant city life of Waikiki and Honolulu, this stunning estate offers the perfect blend of island tranquility and easy access to the best of Oahu. With its breathtaking ocean views, clean contemporary design, and lush tropical surroundings, Diamond Head Grandeur is the ultimate Hawaiian getaway for up to 10 guests.

What We Love About Diamond Head Grandeur:

  • Unparalleled Location: Situated near the gentle waves of Kaalawai Beach and just minutes from Diamond Head, this villa offers the perfect balance of serenity and proximity to shopping, dining, and outdoor adventures.
  • Stunning Outdoor Spaces: Enjoy a cascading infinity pool, jacuzzi spa, and outdoor living area with comfortable seating and dining spaces—ideal for soaking in the Hawaiian sun and taking in the ocean views.
  • Elegant Interiors: The villa’s open-concept design features high ceilings, sleek furnishings, and natural light from sliding glass doors that open to the lanai, blending indoor and outdoor living seamlessly.
  • Luxurious Accommodations: With five spacious bedrooms, each with its own ensuite bathroom, and thoughtful amenities like an elevator for easy access across three floors, comfort and convenience are guaranteed.

As you step into Diamond Head Grandeur, you’re welcomed by an expansive open-concept living area designed for relaxation and entertainment. The main room features a large sectional sofa and armchairs centered around a 55” flat-screen TV, offering plenty of space for guests to unwind. The grand kitchen is fully equipped with modern stainless steel appliances, an island countertop with bar seating, and a formal dining area with seating for eight. Perfect for hosting family meals or celebrations, this space opens directly to the covered lanai overlooking the pool and ocean.

The villa’s five bedrooms are thoughtfully distributed across three floors, offering privacy and luxury for all guests. The primary suite on the upper floor is a true retreat, featuring a king-sized bed, sitting area, and private lanai with panoramic ocean views. The ensuite bathroom includes dual vanities, a walk-in shower, and a separate soaking tub with serene ocean vistas. Also on the upper level are two guest bedrooms: one with a king bed and ensuite bath, and the other with a queen bed and ensuite bath, each with plush linens and elegant decor.

On the main level, you’ll find the first guest bedroom, offering a king bed and ensuite bath, while the second guest bedroom on the lower floor also includes a king bed and ensuite bath. The lower level features a cozy den with comfortable seating, a large flatscreen TV, and a ping-pong table—perfect for movie nights or friendly competitions.

The villa’s outdoor area is nothing short of spectacular. A large infinity pool and jacuzzi are the centerpieces of this tropical oasis, with a spacious lanai offering outdoor seating, a dining area for eight, and a BBQ grill for al fresco meals. Poolside lounge chairs invite you to relax and enjoy the Hawaiian sun, while the stunning views of the Pacific Ocean create an unforgettable backdrop.

Located less than 10 minutes from the world-famous Waikiki Beach, guests have easy access to fine dining, luxury shopping, and vibrant nightlife. For those looking to explore Oahu’s natural beauty, the villa is close to popular activities like snorkeling, hiking, and golfing, as well as the Kahala Hilton Hotel, where you can enjoy dolphin shows and exquisite dining.

Book your stay at Diamond Head Grandeur and experience the epitome of Hawaiian luxury. This exceptional villa promises a vacation filled with elegance, comfort, and unforgettable island memories.

The property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period. Rates based on a 30 day rental period. Please Inquire.

TA-076-121-8560-01
TMK 310400040001


Features

5 Bedrooms, 5.5 Bathrooms

Sleeps 10 Guests

Keypad

Safe

Wifi/Internet

Hot Tub

Private Pool

Iron

Washer

Dryer

Shampoo

Hair Dryer

Outdoor Shower

Linens

Ocean View (Partial)

Toaster Oven

Ice Machine

Blender

Food Processor

Rice Cooker

Kitchen Basics

Disposal

Freezer

Refrigerator

Coffee Maker

Microwave

Dishwasher

Dishes Utensils

Stove

Toaster

Oven

Kettle

Parking space

Free Parking

Ceiling fans

Lanai/Balcony

Garden View

Mountain View

Garage

Private yard

Garden

Sonos Audio System

I-Pod Station / Bluetooth Speaker

Satellite or Cable TV

Stereo

Television

Cooler - Ice Chest

Beach Equipment Rentals Available ($)

Beach Towels

Beach Umbrella


Details

Bedroom Details

Bedroom 1: Master with King (1), Upper Level, En-suite Bathroom, Ocean View, Central AC
Bedroom 2: Guest with King (1), Lower Level, En-suite Bathroom, Central AC
Bedroom 3: Guest with King (1), Main / Center Level, En-suite Bathroom, Central AC
Bedroom 4: Guest with King (1), Upper Level, En-suite Bathroom, Central AC
Bedroom 5: Guest with Queen (1), Upper Level, En-suite Bathroom, Central AC

Bathroom Details

Bedroom 1: Master with En-suite bathroom
Bedroom 2: Guest with En-suite bathroom
Bedroom 3: Guest with En-suite bathroom
Bedroom 4: Guest with En-suite bathroom
Bedroom 5: Guest with En-suite bathroom
Half Bathroom

Beach Details

Cromwell's Beach - 1 minute
Kaalawai Beach - 3 minutes
Beach equipment is available for rent at an additional cost

Pool Details

Private Pool

Location Details

Hawaii Kai Golf Course - 22 minutes
Diamond Head State Monument - 2 minutes
Daniel K. Inouye International Airport - approximately 25 minutes

Villa Notes

Non Smoking
Sorry no pets
A car is recommended
The property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period. Rates based on a 30 day rental period. Please Inquire.


Rates

Travel Dates Bedrooms Min. Night Stay Nightly Rates
May 08, 2025 - August 31, 2025
5 30 $ 1,733 *
September 01, 2025 - October 30, 2025
5 30 $ 2,000 *
October 31, 2025 - November 22, 2025
5 30 $ 1,733 *
November 23, 2025 - December 13, 2025
5 30 $ 2,000 *
December 14, 2025 - January 15, 2026
5 30 $ 2,333 *
January 16, 2026 - January 31, 2026
5 30 $ 1,778 *
February 01, 2026 - August 18, 2026
5 30 $ 1,733 *
August 19, 2026 - August 19, 2026
5 30 $ 4,321 *
August 20, 2026 - August 20, 2026
5 30 $ 4,379 *
August 21, 2026 - August 21, 2026
5 30 $ 4,731 *
August 22, 2026 - August 22, 2026
5 30 $ 4,722 *
August 23, 2026 - August 23, 2026
5 30 $ 3,937 *
August 24, 2026 - August 24, 2026
5 30 $ 4,150 *
August 25, 2026 - August 25, 2026
5 30 $ 3,697 *
August 26, 2026 - August 26, 2026
5 30 $ 4,054 *
August 27, 2026 - August 27, 2026
5 30 $ 4,067 *
August 28, 2026 - August 28, 2026
5 30 $ 4,337 *
August 29, 2026 - August 29, 2026
5 30 $ 4,381 *
August 30, 2026 - August 30, 2026
5 30 $ 3,653 *
August 31, 2026 - August 31, 2026
5 30 $ 3,743 *
September 01, 2026 - September 01, 2026
5 30 $ 3,320 *
September 02, 2026 - September 02, 2026
5 30 $ 3,659 *
September 03, 2026 - September 03, 2026
5 30 $ 3,717 *
September 04, 2026 - September 04, 2026
5 30 $ 4,004 *
September 05, 2026 - September 05, 2026
5 30 $ 4,178 *
September 06, 2026 - September 06, 2026
5 30 $ 3,660 *
September 07, 2026 - September 07, 2026
5 30 $ 3,683 *
September 08, 2026 - September 08, 2026
5 30 $ 3,292 *
September 09, 2026 - September 09, 2026
5 30 $ 3,538 *
September 10, 2026 - September 10, 2026
5 30 $ 3,721 *
September 11, 2026 - September 11, 2026
5 30 $ 3,779 *
September 12, 2026 - September 12, 2026
5 30 $ 3,892 *
September 13, 2026 - September 13, 2026
5 30 $ 3,641 *
September 14, 2026 - September 14, 2026
5 30 $ 3,536 *
September 15, 2026 - September 15, 2026
5 30 $ 3,542 *
September 16, 2026 - September 16, 2026
5 30 $ 3,613 *
September 17, 2026 - September 17, 2026
5 30 $ 3,779 *
September 18, 2026 - September 18, 2026
5 30 $ 3,837 *
September 19, 2026 - September 19, 2026
5 30 $ 3,851 *
September 20, 2026 - September 20, 2026
5 30 $ 3,676 *
September 21, 2026 - September 21, 2026
5 30 $ 3,273 *
September 22, 2026 - September 22, 2026
5 30 $ 3,316 *
September 23, 2026 - September 23, 2026
5 30 $ 3,397 *
September 24, 2026 - September 24, 2026
5 30 $ 3,626 *
September 25, 2026 - September 25, 2026
5 30 $ 3,797 *
September 26, 2026 - September 26, 2026
5 30 $ 3,863 *
September 27, 2026 - September 27, 2026
5 30 $ 3,661 *
September 28, 2026 - September 28, 2026
5 30 $ 3,299 *
September 29, 2026 - September 29, 2026
5 30 $ 3,256 *
September 30, 2026 - September 30, 2026
5 30 $ 3,303 *
October 01, 2026 - October 01, 2026
5 30 $ 3,524 *
October 02, 2026 - October 02, 2026
5 30 $ 3,761 *
October 03, 2026 - October 03, 2026
5 30 $ 3,727 *
October 04, 2026 - October 04, 2026
5 30 $ 3,523 *
October 05, 2026 - October 05, 2026
5 30 $ 3,209 *
October 06, 2026 - October 06, 2026
5 30 $ 3,148 *
October 07, 2026 - October 07, 2026
5 30 $ 3,370 *
October 08, 2026 - October 08, 2026
5 30 $ 3,621 *
October 09, 2026 - October 09, 2026
5 30 $ 4,028 *
October 10, 2026 - October 10, 2026
5 30 $ 3,889 *
October 11, 2026 - October 11, 2026
5 30 $ 3,730 *
October 12, 2026 - October 12, 2026
5 30 $ 3,383 *
October 13, 2026 - October 13, 2026
5 30 $ 3,168 *
October 14, 2026 - October 14, 2026
5 30 $ 3,392 *
October 15, 2026 - October 15, 2026
5 30 $ 3,639 *
October 16, 2026 - October 16, 2026
5 30 $ 3,769 *
October 17, 2026 - October 17, 2026
5 30 $ 3,571 *
October 18, 2026 - October 18, 2026
5 30 $ 3,468 *
October 19, 2026 - October 19, 2026
5 30 $ 3,139 *
October 20, 2026 - October 20, 2026
5 30 $ 3,247 *
October 21, 2026 - October 21, 2026
5 30 $ 3,392 *
October 22, 2026 - October 22, 2026
5 30 $ 3,716 *
October 23, 2026 - October 23, 2026
5 30 $ 3,740 *
October 24, 2026 - October 24, 2026
5 30 $ 3,460 *
October 25, 2026 - October 25, 2026
5 30 $ 3,294 *
October 26, 2026 - October 28, 2026
5 30 $ 3,139 *
October 29, 2026 - October 29, 2026
5 30 $ 3,421 *
USD rates above based on approximate currency conversion. Holiday dates may not be listed in rate chart. Rates are subject to change without notice. Please confirm rate, holiday dates, and currency with your Villa Specialist at time of booking.

Tax Service Charge Details *

Please add 17.962% tax to all rates
Departure cleaning fee: $1,980 plus tax
Mid-stay cleaning after 7 nights: $550 plus tax
Service fee: $295 plus tax
2% Booking fee

Minimum Stay Details

Minimum night stay may vary by season. Contact a villa specialist to confirm.

Accidental Damage Waiver

A $249 Accidental Damage Waiver applies to every reservation.

Exclusive Offers

When you choose to book with Villas of Distinction for MileagePlus, you can exclusively earn 3 miles per $1 spent on your villa experience, excluding taxes, fees and optional fees.
To qualify for 3 miles per $1 spent, bookings must be made through the Villas of Distinction for United MileagePlus program. Miles earned are awarded to only one traveler per villa booking. The actual number of miles earned by a member will be based upon the total base nightly villa rate excluding taxes, fees and optional fees. MileagePlus number must be provided prior to travel for mileage offer to be fulfilled. Miles are posted to member's accounts 6-8 weeks after travel has been completed. Bookings must be paid in U.S. currency. New bookings only. Offers are subject to availability, capacity-controlled and may be changed or withdrawn at any time without notice. Other restrictions may apply.

Calendar

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Location

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