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 People

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
December 14, 2025 - December 25, 2025
5 30 $2,100 *
December 26, 2025 - December 26, 2025
5 10 $2,100 *
December 27, 2025 - January 10, 2026
5 30 $2,100 *
January 11, 2026 - January 31, 2026
5 30 $1,401 *
February 01, 2026 - November 15, 2026
5 30 $1,561 *
November 16, 2026 - November 30, 2026
5 30 $1,794 *
December 01, 2026 - January 31, 2027
5 30 $2,200 *
February 01, 2027 - February 01, 2027
5 30 $4,570 *
February 02, 2027 - February 02, 2027
5 30 $4,660 *
February 03, 2027 - February 03, 2027
5 30 $4,840 *
February 04, 2027 - February 04, 2027
5 30 $4,753 *
February 05, 2027 - February 05, 2027
5 30 $4,900 *
February 06, 2027 - February 06, 2027
5 30 $4,875 *
February 07, 2027 - February 07, 2027
5 30 $4,509 *
February 08, 2027 - February 08, 2027
5 30 $4,244 *
February 09, 2027 - February 09, 2027
5 30 $4,352 *
February 10, 2027 - February 10, 2027
5 30 $4,607 *
February 11, 2027 - February 11, 2027
5 30 $4,579 *
February 12, 2027 - February 12, 2027
5 30 $5,165 *
February 13, 2027 - February 13, 2027
5 30 $5,235 *
February 14, 2027 - February 14, 2027
5 30 $4,934 *
February 15, 2027 - February 15, 2027
5 30 $4,709 *
February 16, 2027 - February 16, 2027
5 30 $4,495 *
February 17, 2027 - February 17, 2027
5 30 $4,814 *
February 18, 2027 - February 18, 2027
5 30 $4,839 *
February 19, 2027 - February 19, 2027
5 30 $4,943 *
February 20, 2027 - February 20, 2027
5 30 $4,841 *
February 21, 2027 - February 21, 2027
5 30 $4,443 *
February 22, 2027 - February 22, 2027
5 30 $4,125 *
February 23, 2027 - February 23, 2027
5 30 $4,141 *
February 24, 2027 - February 24, 2027
5 30 $4,364 *
February 25, 2027 - February 25, 2027
5 30 $4,522 *
February 26, 2027 - February 26, 2027
5 30 $4,661 *
February 27, 2027 - February 27, 2027
5 30 $4,479 *
February 28, 2027 - February 28, 2027
5 30 $4,191 *
March 01, 2027 - March 01, 2027
5 30 $3,989 *
March 02, 2027 - March 02, 2027
5 30 $4,028 *
March 03, 2027 - March 03, 2027
5 30 $4,212 *
March 04, 2027 - March 04, 2027
5 30 $4,493 *
March 05, 2027 - March 05, 2027
5 30 $4,688 *
March 06, 2027 - March 06, 2027
5 30 $4,530 *
March 07, 2027 - March 07, 2027
5 30 $4,379 *
March 08, 2027 - March 08, 2027
5 30 $4,341 *
March 09, 2027 - March 09, 2027
5 30 $4,412 *
March 10, 2027 - March 10, 2027
5 30 $4,503 *
March 11, 2027 - March 11, 2027
5 30 $4,862 *
March 12, 2027 - March 12, 2027
5 30 $4,975 *
March 13, 2027 - March 13, 2027
5 30 $4,813 *
March 14, 2027 - March 14, 2027
5 30 $4,608 *
March 15, 2027 - March 15, 2027
5 30 $4,586 *
March 16, 2027 - March 16, 2027
5 30 $4,443 *
March 17, 2027 - March 17, 2027
5 30 $4,242 *
March 18, 2027 - March 18, 2027
5 30 $4,520 *
March 19, 2027 - March 19, 2027
5 30 $4,531 *
March 20, 2027 - March 20, 2027
5 30 $4,452 *
March 21, 2027 - March 21, 2027
5 30 $4,286 *
March 22, 2027 - March 22, 2027
5 30 $4,292 *
March 23, 2027 - March 23, 2027
5 30 $4,260 *
March 24, 2027 - March 24, 2027
5 30 $4,117 *
March 25, 2027 - March 25, 2027
5 30 $4,348 *
March 26, 2027 - March 26, 2027
5 30 $5,012 *
March 27, 2027 - March 27, 2027
5 30 $4,945 *
March 28, 2027 - March 28, 2027
5 30 $4,786 *
March 29, 2027 - March 29, 2027
5 30 $4,231 *
March 30, 2027 - March 30, 2027
5 30 $4,209 *
March 31, 2027 - March 31, 2027
5 30 $4,109 *
April 01, 2027 - April 01, 2027
5 30 $4,249 *
April 02, 2027 - April 02, 2027
5 30 $4,467 *
April 03, 2027 - April 03, 2027
5 30 $4,427 *
April 04, 2027 - April 04, 2027
5 30 $4,261 *
April 05, 2027 - April 05, 2027
5 30 $4,092 *
April 06, 2027 - April 06, 2027
5 30 $4,014 *
April 07, 2027 - April 07, 2027
5 30 $4,028 *
April 08, 2027 - April 08, 2027
5 30 $3,950 *
April 09, 2027 - April 09, 2027
5 30 $4,143 *
April 10, 2027 - April 10, 2027
5 30 $4,031 *
April 11, 2027 - April 11, 2027
5 30 $3,865 *
April 12, 2027 - April 12, 2027
5 30 $3,536 *
April 13, 2027 - April 13, 2027
5 30 $3,529 *
April 14, 2027 - April 14, 2027
5 30 $3,714 *
April 15, 2027 - April 15, 2027
5 30 $3,729 *
April 16, 2027 - April 16, 2027
5 30 $3,884 *
April 17, 2027 - April 17, 2027
5 30 $3,762 *
April 18, 2027 - April 18, 2027
5 30 $3,631 *
April 19, 2027 - April 19, 2027
5 30 $3,119 *
April 20, 2027 - April 20, 2027
5 30 $3,083 *
April 21, 2027 - April 21, 2027
5 30 $3,310 *
April 22, 2027 - April 22, 2027
5 30 $3,390 *
April 23, 2027 - April 23, 2027
5 30 $3,393 *
April 24, 2027 - April 24, 2027
5 30 $3,441 *
April 25, 2027 - April 25, 2027
5 30 $3,296 *
April 26, 2027 - April 26, 2027
5 30 $2,825 *
April 27, 2027 - April 27, 2027
5 30 $2,840 *
April 28, 2027 - April 28, 2027
5 30 $3,118 *
April 29, 2027 - April 29, 2027
5 30 $3,318 *
April 30, 2027 - April 30, 2027
5 30 $3,352 *
May 01, 2027 - May 01, 2027
5 30 $3,454 *
May 02, 2027 - May 02, 2027
5 30 $3,227 *
May 03, 2027 - May 03, 2027
5 30 $2,865 *
May 04, 2027 - May 04, 2027
5 30 $2,835 *
May 05, 2027 - May 05, 2027
5 30 $3,104 *
May 06, 2027 - May 06, 2027
5 30 $3,415 *
May 07, 2027 - May 07, 2027
5 30 $3,522 *
May 08, 2027 - May 08, 2027
5 30 $3,656 *
May 09, 2027 - May 09, 2027
5 30 $3,411 *
May 10, 2027 - May 10, 2027
5 30 $3,057 *
May 11, 2027 - May 11, 2027
5 30 $3,000 *
May 12, 2027 - May 12, 2027
5 30 $3,149 *
May 13, 2027 - May 13, 2027
5 30 $3,631 *
May 14, 2027 - May 14, 2027
5 30 $3,826 *
May 15, 2027 - May 15, 2027
5 30 $3,894 *
May 16, 2027 - May 16, 2027
5 30 $3,687 *
May 17, 2027 - May 17, 2027
5 30 $3,331 *
May 18, 2027 - May 18, 2027
5 30 $3,244 *
May 19, 2027 - May 19, 2027
5 30 $3,274 *
May 20, 2027 - May 20, 2027
5 30 $3,905 *
May 21, 2027 - May 21, 2027
5 30 $4,010 *
May 22, 2027 - May 22, 2027
5 30 $3,931 *
May 23, 2027 - May 23, 2027
5 30 $3,811 *
May 24, 2027 - May 24, 2027
5 30 $3,537 *
May 25, 2027 - May 25, 2027
5 30 $3,355 *
May 26, 2027 - May 26, 2027
5 30 $3,232 *
May 27, 2027 - May 27, 2027
5 30 $3,990 *
May 28, 2027 - May 28, 2027
5 30 $4,599 *
May 29, 2027 - May 30, 2027
5 30 $4,515 *
May 31, 2027 - May 31, 2027
5 30 $4,327 *
June 01, 2027 - June 01, 2027
5 30 $3,531 *
June 02, 2027 - June 02, 2027
5 30 $3,409 *
June 03, 2027 - June 03, 2027
5 30 $4,089 *
June 04, 2027 - June 04, 2027
5 30 $4,125 *
June 05, 2027 - June 05, 2027
5 30 $4,069 *
June 06, 2027 - June 06, 2027
5 30 $4,079 *
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
Please note: for all reservations beginning January 1, 2026, an additional .75% "green tax" will go into affect. Total taxes will increase to 18.712%.
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.

Calendar

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Location

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