Diamond Head Hillside Estate**

Honolulu, HI 4 Bedrooms Vacation Rental

4 Beds
4Baths
10Sleeps
Share
image
Overview
Room Details
Amenities
Reviews
View Map

Rooms


Amenities

Private pool
Air conditioning
Hot Tub
Walk to Shops / Restaurants

Reviews

No Reviews

Description

Wake up to soaring ceilings, lush tropical gardens, and the effortless flow of island living at Diamond Head Hillside Estate. Tucked within a private Honolulu setting, this thoughtfully designed luxury estate offers nearly 5,900 square feet of beautifully appointed indoor-outdoor living space, including an exceptional collection of wellness and recreation amenities, and a detached guest house spanning an additional 960 square feet. Whether you're gathering with family, working remotely for an extended stay, or simply seeking room to unwind, this distinctive holiday home delivers comfort, privacy, and a true sense of place.

What You'll Love About Diamond Head Hillside Estate
• Nearly 4,900 square feet of thoughtfully designed indoor living space
• Resort-style outdoor retreat with pool, hot tub, cold plunge, and fire pit
• Detached guest house with private living room, office, and additional sleeping accommodations
• Wellness-focused amenities including a home gym, sauna, and outdoor shower
• Recreation features including an unofficial pickleball court, ping pong table, and shuffleboard

Living & Dining
The main residence is defined by its soaring 14-foot ceilings, abundant natural light, and seamless connection to the outdoors. Expansive gathering spaces invite conversation and relaxation, while oversized windows frame views of the surrounding tropical landscape. Custom built-ins, warm finishes, and carefully curated furnishings create an atmosphere that feels both elevated and welcoming.

The open-concept great room flows effortlessly into the dining area and covered lanai, making it easy to move between indoor entertaining and outdoor living throughout the day.

Chef-Ready Kitchen
At the heart of the home, the spacious kitchen is designed for everything from casual breakfasts to memorable dinners with family and friends. Open sightlines keep everyone connected while generous prep space and convenient access to the dining and outdoor areas make entertaining effortless.

Outdoor Oasis
Designed for year-round enjoyment, the outdoor spaces feel like a private retreat. Spend sunny afternoons cooling off in the sparkling pool, soak in the hot tub beneath swaying palms, or recharge in the cold plunge after a workout or sauna session.

Covered lanais provide comfortable spaces for morning coffee and evening gatherings, while the fire pit creates the perfect setting to linger outdoors after sunset. Mature landscaping surrounds the property, adding privacy and a tranquil backdrop to every moment.
For guests who enjoy staying active, the property also features an unofficial pickleball court, ping pong table, shuffleboard, and a dedicated outdoor shower.

Sleeping Quarters
• Primary Suite: Spacious private suite with en-suite bathroom and king bed
• Bedroom 2: Ensuite guest bedroom with queen bed
• Bedroom 3: Ensuite guest bedroom with queen bed
• Detached Guest House Bedroom: Private bedroom with dedicated bathroom, complete with a king bed
• Detached Guest House Living Room: Full-size sleeper sofa for additional guests

Extras
• Central air conditioning throughout
• Dedicated home gym
• Private sauna
• Office workspace in the guest house
• Security system
• Two electric vehicle charging stations
• Solar panels and battery backup system
• Generous storage throughout the property

Nearby
Nearby beaches, dining, shopping, and attractions can be added once the neighborhood or district is confirmed.

Good to Know
• Pets are considered on a case-by-case basis. Subject to a fee determined at the time of the request.
• Exterior security cameras monitor the perimeter of the property only. There are no cameras within the home or private yard areas.
• This residence is offered exclusively for 30-day rental periods. Rates are based on a full 30-day stay. Please inquire for availability and details.
• Ideal for families, couples traveling together, and digital nomads seeking an extended Hawaii stay
• TAT ID: TA-177-407-7952-01
• TMK / Parcel ID: 1310200080000

From morning workouts and poolside afternoons to evenings gathered around the fire pit, Diamond Head Hillside Estate offers the space, privacy, and elevated comforts that make longer stays in Honolulu feel effortless. Reserve your dates and settle into island living at its finest.

Room

Beds


Primary Bedroom

King (1)

Ensuite Bathroom, Garden View, Central A/C, Ceiling Fan, Ceiling Fan


Guest Bedroom 2

Queen (1)

Ensuite Bathroom, Garden View, Central A/C, Ceiling Fan


Guest Bedroom 3

Queen (1)

Ensuite Bathroom, Garden View, Central A/C, Ceiling Fan


Guest Bedroom 4

King (1) Sofa Bed (1)

Ensuite Bathroom, Guest House, Full Sofa Bed, Central A/C, Ceiling Fan, Blackout Drapes


Primary Bedroom Ensuite

full bathroom


Guest Bedroom 2 Ensuite

full bathroom


Guest Bedroom 3 Ensuite

full bathroom


Guest Bedroom 4 Ensuite

full bathroom


Powder Room 1

half bathroom

Nearby Activities

  • Spa and wellness
  • Zoo
  • Museums
  • Hiking
  • Fishing
  • Watersports
  • Cycling
  • Tennis
  • Scuba diving or Snorkeling
  • Shopping
  • Horseback riding
  • Golfing
  • Bike path

Kitchen and Dining

  • Dining Area
  • Kitchen Basics
  • Kitchen
  • Refrigerator
  • Coffee Maker
  • Microwave
  • Dishwasher
  • Dishes Utensils
  • Stove
  • Toaster
  • Oven
  • BBQ
  • Freezer
  • Kettle
  • Espresso Machine
  • Ice Machine
  • Blender
  • Wine Fridge
  • Crockpot
  • Rice Cooker
  • Coffee Grinder
  • Food Processor
  • Mixer
  • Juicer
  • Disposal
  • Coffee Filter

Amenities

  • Essentials
  • Shampoo
  • Dryer
  • Washer
  • Fitness Room
  • Hair Dryer
  • Linens
  • Iron
  • Parking space
  • Safe
  • Private Entrance
  • Extra Pillows And Blankets
  • Wifi/Internet
  • Fire pit
  • EV Charger

Suitability

  • Hot Water
  • Children Welcome
  • Pets Considered
  • Smoking Not Allowed
  • Minimum Age Limit
  • Street Parking
  • Free Parking
  • Ceiling fans
  • Suitable for Elderly
  • Air Conditioning
  • Long Term Stays Allowed
  • Bath Tub

Emergency

  • Emergency Medical Contact
  • Emergency Police Contact
  • Emergency Fire Contact

Cleanliness

  • Self Check In / Check Out

Safety Features

  • Carbon Monoxide Detector
  • First Aid Kit
  • Fire Extinguisher
  • Smoke Detector
  • Outdoor Lighting
  • Security Cameras

Entertainment

  • Television
  • Laptop Friendly
  • Smart TV
  • Sonos Audio System
  • Printer/Scanner/Fax
  • Ping Pong Table

Pool/Spa

  • Hot Tub
  • Private Pool
  • Sauna

Internal Amenities

  • Beach Towels
  • Beach Chairs
  • Additional Bedding

Outdoor Amenities

  • Beach Umbrella
  • Outdoor Shower
  • Garden
  • Private yard
  • Outdoor seating
  • Pickleball & Tennis Court

Themes

  • Family
  • Luxury
  • Romantic

Car

  • Car Necessary
  • Car Recommended

Location/Property Types

  • Garden View
  • Walk to Shops / Restaurants

No Reviews.