$1,950 - $2,500USD per night
Diamond Head Grandeur
Pool Hot tub Ocean View Walk to Beach
$1,950 - $2,500USD per night
5 Bedrooms(10 guests)
5.5 Bathrooms(5 ensuites)

Discover serenity and relaxation in your own private retreat at Diamond Head Grandeur, nestled in the heart of Kahala on Oahu. Just steps away from the iconic Diamond Head State Monument and a short drive from downtown Honolulu and Waikiki, this exquisite 5-bedroom, 5.5-bathroom villa offers the perfect blend of convenience and tranquility.

Designed with a blend of modern elegance and island charm by a renowned Hawaii & California homebuilder, this villa boasts a clean and contemporary aesthetic both inside and out. Surrounded by meticulously landscaped tropical gardens, it offers a luxurious sanctuary for your island escape.

The spacious main room features an open-concept layout with high ceilings, sleek furnishings, and ample natural light streaming in through expansive windows. A sliding panel wall opens to reveal stunning ocean views and invites in the gentle trade winds, creating a seamless indoor-outdoor living experience. Relax on the plush sectional sofa while enjoying entertainment on the 55” flat screen TV, or gather around the grand kitchen’s island countertop, equipped with modern stainless steel appliances, perfect for hosting and culinary adventures.

The villa’s accommodations include a king bed guest suite on the main floor with an ensuite bath, while the lower level hosts a cozy den with plush seating and a large flat screen TV, ideal for movie nights or friendly ping-pong matches. Another king bed guest suite with a bathroom is also located on this level.

Ascending to the upper floor, you’ll find the breathtaking primary bedroom boasting a king bed, sitting area, and private lanai balcony offering panoramic ocean views. The attached luxury ensuite features dual vanities, a walk-in shower, and a separate soaking tub overlooking the azure waters. Two additional guest bedrooms on this level provide comfortable accommodations, including a king bed suite and a queen bed suite, each with its own ensuite bath.

Outside, the villa’s backyard oasis beckons with a cascading infinity pool, jacuzzi spa, and gas-powered torches for ambient lighting. A covered lanai with outdoor seating overlooks the pool, providing the perfect setting for al fresco dining or simply lounging in the Hawaiian sun. Two designated parking spaces are available, with ample street parking nearby.

Experience the best of Oahu’s attractions and activities from this prime location, just minutes from Waikiki Beach, Honolulu, and the airport. Whether you’re snorkeling in crystal-clear waters, hiking scenic trails, or indulging in world-class dining and shopping, Diamond Head Grandeur promises an unforgettable Hawaiian getaway.

Note: The property is exclusively available for 30-day rentals, ensuring privacy and exclusivity for your stay. Rates are based on a 30-day rental period. Please inquire for more details.


TMK 310400040001

Read more
See more photos

Villa Details

5 bedrooms,
5 ensuites
  • Bedroom 1
    • King bed
    • Ensuite Bath
    • Air conditioned
    • Primary: Upper Level, Ocean View, Central AC, Ensuite with bathtub and shower
  • Bedroom 2
    • King bed
    • Ensuite Bath
    • Air conditioned
    • Lower Level, Central AC
  • Bedroom 3
    • King bed
    • Ensuite Bath
    • Air conditioned
    • Main / Center Level, Central AC
  • Bedroom 4
    • King bed
    • Ensuite Bath
    • Air conditioned
    • Upper Level, Central AC
  • Bedroom 5
    • Queen bed
    • Ensuite Bath
    • Air conditioned
    • Upper Level, Central AC

Fully-equipped villa, offering
many features and amenities

  • Central AC
  • Wifi
  • Media Room
  • Satellite TV
  • Indoor Sound System
  • Ping Pong Table
  • Parking for 2 cars
  • Pool
  • Hot tub
  • Alfresco Shower
  • Alfresco Dining
  • BBQ
  • Beach Chairs and Loungers

Additional services offered at Diamond Head Grandeur

  • concierge
  • Housekeeper
  • Chef
  • Airport Transfer
  • Car Rental
  • Pre Stocking

Additional information & house rules

House Rules
  • No Pets
  • No Events
  • No Smoking
  • Suitable for children (2-12)
Check In4:00 pm
Check Out10:00 am
House Rules
  • No Pets
  • No Events
  • No Smoking
  • Suitable for children (2-12)
Check In - Check Out
4:00 pm - 10:00 am


Hawaii, Oahu
The villa address will be provide at the time of booking.

Our guest-first focus

You’re always our top priority–we’ve got you covered on all your travel needs before, during and after your stay.

Hand-selected villas

Our standards are high. Each and every villa we offer has been visited or thoroughly reviewed by a member of our team.

A trusted network

We only work with partners we know and trust, so you can count on them to reflect our values and standards.

Our mission is to transform our experience and relationships into a unique offering for you.
Client-first focusHand-select villasA trusted network

Similar villas

Hand-selected villas with features similar to Diamond Head Grandeur