Diamond Head Hillside Estate**

Diamond Head Hillside Estate**

Diamond Head, Oahu, Hawaii
  • 4 beds
  • 4 baths
  • Sleeps 10

Overview

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.

Property Highlights

  • 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
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.

RoomsOccupancy

  • Primary Bedroom

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

    • King (1)

  • Guest Bedroom 2

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

    • Queen (1)

  • Guest Bedroom 4

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

    • King (1)
    • Sofa Bed (1)

  • Guest Bedroom 3

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

    • Queen (1)

  • Primary Bedroom Ensuite

    • Guest Bedroom 2 Ensuite

      • Guest Bedroom 3 Ensuite

        • Guest Bedroom 4 Ensuite

          • Powder Room 1

            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

            Car

            • Car Necessary
            • Car Recommended

            Property Manager

            • VIP Luxury Villas

            October 2026

            SMTWTFS
            30$1,66731$1,667

            November 2026

            SMTWTFS
            01$1,66702$1,66703$1,66704$1,66705$1,66706$1,66707$1,667
            08$1,66709$1,66710$1,66711$1,66712$1,66713$1,66714$1,667
            15$1,66716$1,66717$1,66718$1,66719$1,66720$1,66721$1,667
            22$1,66723$1,66724$1,66725$1,66726$1,66727$1,66728$1,667
            29$1,66730$1,667

            December 2026

            SMTWTFS
            01$2,16602$2,16603$2,16604$2,16605$2,166
            06$2,16607$2,16608$2,16609$2,16610$2,16611$2,16612$2,166
            13$2,16614$2,16615$2,16616$2,16617$2,16618$2,16619$2,166
            20$2,16621$2,16622$2,16623$2,16624$2,16625$2,16626$2,166
            27$2,16628$2,16629$2,16630$2,16631$2,166

            January 2027

            SMTWTFS
            01$2,16602$2,166
            03$2,16604$2,16605$2,16606$2,16607$2,16608$2,16609$2,166
            10$2,16611$2,16612$2,16613$2,16614$2,16615$2,16616$2,166
            17$2,16618$2,16619$2,16620$2,16621$2,16622$2,16623$2,166
            24$2,16625$2,16626$2,16627$2,16628$2,16629$1,66730$1,667
            31$1,667

            February 2027

            SMTWTFS
            01$1,66702$1,66703$1,66704$1,66705$1,66706$1,667
            07$1,66708$1,66709$1,66710$1,66711$1,66712$1,66713$1,667
            14$1,66715$1,66716$1,66717$1,66718$1,66719$1,66720$1,667
            21$1,66722$1,66723$1,66724$1,66725$1,66726$1,66727$1,667
            28$1,667

            March 2027

            SMTWTFS
            01$1,66702$1,66703$1,66704$1,66705$1,66706$1,667
            07$1,66708$1,66709$1,66710$1,66711$1,66712$1,66713$1,667
            14$1,66715$1,66716$1,66717$1,66718$1,66719$1,66720$1,667
            21$1,66722$1,66723$1,66724$1,66725$1,66726$1,66727$1,667
            28$1,66729$1,66730$1,66731$1,667

            April 2027

            SMTWTFS
            01$1,66702$1,66703$1,667
            04$1,66705$1,66706$1,66707$1,66708$1,66709$1,66710$1,667
            11$1,66712$1,66713$1,66714$1,66715$1,66716$1,66717$1,667
            18$1,66719$1,66720$1,66721$1,66722$1,66723$1,66724$1,667
            25$1,66726$1,66727$1,66728$1,66729$1,66730$1,667

            May 2027

            SMTWTFS
            01$1,667
            02$1,66703$1,66704$1,66705$1,66706$1,66707$1,66708$1,667
            09$1,66710$1,66711$1,66712$1,66713$1,66714$1,66715$1,667
            16$1,66717$1,66718$1,66719$1,66720$1,66721$1,66722$1,667
            23$1,66724$1,66725$1,66726$1,66727$1,66728$1,66729$1,667
            30$1,66731$1,667

            June 2027

            SMTWTFS
            01$2,00002$2,00003$2,00004$2,00005$2,000
            06$2,00007$2,00008$2,00009$2,00010$2,00011$2,00012$2,000
            13$2,00014$2,00015$2,00016$2,00017$2,00018$2,00019$2,000
            20$2,00021$2,00022$2,00023$2,00024$2,00025$1,66726
            27282930

            July 2027

            SMTWTFS
            010203
            04050607080910
            11121314151617
            18192021222324
            25262728293031

            August 2027

            SMTWTFS
            01020304050607
            08091011121314
            1516$2,00017$2,00018$2,00019$2,00020$2,00021
            222324252627$2,00028$2,000
            293031

            September 2027

            SMTWTFS
            01020304
            05060708091011
            12131415161718
            192021$1,66722$1,667232425
            2627282930

            October 2027

            SMTWTFS
            0102
            03040506070809
            10111213141516
            17181920212223
            242526272829$1,66730$1,667
            31$1,667

            November 2027

            SMTWTFS
            01$1,66702$1,66703$1,66704$1,66705$1,66706$1,667
            07$1,66708$1,66709$1,66710$1,66711$1,66712$1,66713$1,667
            14$1,66715$1,66716$1,66717$1,66718$1,66719$1,66720$1,667
            21$1,66722$1,66723$1,66724$1,66725$1,66726$1,66727$1,667
            28$1,66729$1,66730$1,667

            December 2027

            SMTWTFS
            01$2,16602$2,16603$2,16604$2,166
            05$2,16606$2,16607$2,16608$2,16609$2,16610$2,16611$2,166
            12$2,16613$2,16614$2,16615$2,16616$2,16617$2,16618$2,166
            19$2,16620$2,16621$2,16622$2,16623$2,16624$2,16625$2,166
            26$2,16627$2,16628$2,16629$2,16630$2,16631$2,166

            January 2028

            SMTWTFS
            01$2,166
            02$2,16603$2,16604$2,16605$2,16606$2,16607$2,16608$2,166
            09$2,16610$2,16611$2,16612$2,16613$2,16614$2,16615$2,166
            16$2,16617$2,16618$2,16619$2,16620$2,16621$2,16622$2,166
            23$2,16624$2,16625$2,16626$2,16627$2,35928$2,47129$2,452
            30$2,33631$2,297

            February 2028

            SMTWTFS
            01$2,24402$2,31203$2,45004$2,52405$2,511
            06$2,40207$2,33608$2,26109$2,34510$2,50311$2,56412$2,561
            13$2,47114$2,39615$2,33216$2,44917$2,62318$2,78819$2,743
            20$2,59921$2,44522$2,23523$2,31524$2,46625$2,53226$2,496
            27$2,35328$2,20929$2,139

            March 2028

            SMTWTFS
            01$2,22802$2,37403$2,85304$2,857
            05$2,73806$2,66507$2,62708$2,72009$2,84510$2,95011$2,964
            12$2,72713$2,69514$2,63115$2,67216$2,74117$2,81718$2,806
            19$2,71920$2,66621$2,62622$2,67823$2,75924$2,82025$2,763
            26$2,77927$2,65928$2,61529$2,64530$2,72331$2,766

            April 2028

            SMTWTFS
            01$2,706
            02$2,28503$2,22704$2,19805$2,24506$2,32307$2,37308$2,297
            09$2,20110$2,10311$2,05812$2,09513$2,17514$2,31515$2,234
            16$2,12317$1,89318$1,89319$1,89320$2,01621$2,094
            Back to Top