Seaside Hideaway 5BR Estate

Seaside Hideaway 5BR Estate

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

Overview

Privately set in one of Oahu’s most prominent residential neighborhoods, Seaside Hideaway 5BR Estate is a discreet Diamond Head retreat offering layered privacy, elevated design, and a rare sense of seclusion just minutes from Waikiki. Comprised of a three-bedroom main house and two separate studio cottage bungalows, this intimate estate blends classic island elegance with modern European finishes and resort-style outdoor living.

Property Highlights

  • Private Diamond Head estate with main house and two detached studio cottages
  • Elevated setting with ocean views from the primary suite and select lanais
  • Secluded pool, Jacuzzi, and outdoor shower tucked below the main lanai
  • High-end interiors featuring Agape Italy bathrooms and SieMatic Germany kitchen
  • Prime location near Waikiki, Kahala, beaches, and Diamond Head landmarks
Privately set in one of Oahu’s most prominent residential neighborhoods, Seaside Hideaway 5BR Estate is a discreet Diamond Head retreat offering layered privacy, elevated design, and a rare sense of seclusion just minutes from Waikiki. Comprised of a three-bedroom main house and two separate studio cottage bungalows, this intimate estate blends classic island elegance with modern European finishes and resort-style outdoor living. What You’ll Love About Seaside Hideaway 5BR Estate • Private Diamond Head estate with main house and two detached studio cottages • Elevated setting with ocean views from the primary suite and select lanais • Secluded pool, Jacuzzi, and outdoor shower tucked below the main lanai • High-end interiors featuring Agape Italy bathrooms and SieMatic Germany kitchen • Prime location near Waikiki, Kahala, beaches, and Diamond Head landmarks Living & Dining The main house offers relaxed island elegance with a modern sensibility. Light-filled interiors, refined furnishings, and thoughtful flow create a welcoming environment for gathering and unwinding. A covered lanai extends the living space outdoors, providing a comfortable perch for lounging while gazing toward Diamond Head’s dramatic coastline. Chef-Ready Kitchen The kitchen is outfitted with sleek SieMatic cabinetry from Germany and modern appliances, combining function with clean-lined design. Whether preparing casual breakfasts or relaxed dinners at home, the space supports effortless everyday living. Sleeping Quarters The estate’s layout offers flexibility and privacy across the main house and detached cottages. • Primary Suite: Located in the main house, featuring ocean views and a private outdoor lanai • Additional Bedrooms: Two bedrooms in the main house, styled with comfort and simplicity • Studio Cottage Bungalows: Two separate studio suites perched above the main house, each with a private entrance, ensuite bathroom, kitchenette, and sweeping views Together, the five-bedroom configuration makes the estate well suited for families, extended stays, or groups seeking both togetherness and personal space. Outdoor Oasis Below the main lanai, a secluded outdoor area reveals a private pool, Jacuzzi, and outdoor shower, creating a quiet retreat shielded from view. The layered layout of the property enhances privacy throughout, allowing guests to move easily between shared and personal spaces. Extras Parking is available for two vehicles on the driveway in front of the garage. The garage itself is not accessible to guests. Please note that from the entry gate at the driveway, the main house and guest cottages are accessed via a steep stairway. Mandatory weekly cleanings are required by the owner at an additional cost. Nearby The Diamond Head neighborhood is known for its quiet, upscale residential feel and strong beach community lifestyle. Local beaches, Diamond Head surf breaks, scenic lookouts, and coastal walking routes are within walking distance. Waikiki is approximately a five-minute drive, while Kahala Mall and the Kahala Hotel & Resort are just three minutes away, offering a wide array of dining, shopping, and leisure options. Good to Know • Rates and fees are subject to change. Minimum stay requirements may apply. Inquire for possible discounts. • Online bookings are subject to manager or owner approval. • Mandatory weekly cleanings are required at an additional cost. • For stays of 21–30 days or longer, a utility fee or utility deposit will be charged. • For 30-day rentals, the property is made exclusively available to the renter for the full rental period. Rates are based on a 30-day term. Please inquire for details. This vacation home is registered as a Transient Accommodation with the State of Hawaii. • Hawaii Tax ID: W20574188-01 • TMK: 310380140000 Designed for privacy, comfort, and flexibility, Seaside Hideaway 5BR Estate offers a refined Diamond Head escape with space to gather and room to retreat. Reserve your stay and experience elevated island living just moments from the energy of Waikiki.

RoomsOccupancy

  • Plumeria Bungalow

    King sized bed (two twins connected), Ensuite bathroom

    • King (1)

  • Plumeria Bungalow Ensuite

    • Ilima Bungalow

      King sized bed (two twins connected), Ensuite bathroom

      • King (1)

    • Primary Bedroom

      Ocean views, balcony, ceiling fan, television, Ensuite bathroom

      • King (1)

    • Guest Bedroom 2

      Garden view, ceiling fan, television.

      • King (1)

    • Guest Bedroom 3

      Garden view, ceiling fan, television.

      • King (1)

    • Ilima Bungalow Ensuite

      • Primary Bedroom Ensuite

        • Guest Bathroom

          Nearby Activities

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

          Kitchen and Dining

          • Dining Area
          • Kitchen Basics
          • Kitchen
          • Refrigerator
          • Coffee Maker
          • Microwave
          • Dishwasher
          • Dishes Utensils
          • Stove
          • Toaster
          • Oven
          • BBQ
          • Freezer
          • Espresso Machine
          • Ice Machine
          • Blender
          • Wine Fridge
          • Rice Cooker

          Amenities

          • Essentials
          • Shampoo
          • Dryer
          • Washer
          • Hair Dryer
          • Linens
          • Iron
          • Parking space
          • Private Entrance
          • Lock Box
          • Wifi/Internet

          Safety Features

          • Smoke Detector
          • Security Cameras

          Suitability

          • Air Conditioning
          • Bath Tub
          • Hot Water
          • Street Parking
          • Free Parking

          Entertainment

          • Television
          • Satellite or Cable TV

          Pool/Spa

          • Hot Tub
          • Private Pool

          Internal Amenities

          • Beach Towels

          Outdoor Amenities

          • Outdoor Shower
          • Private yard
          • Beach Equipment Rentals Available ($)
          • Lanai/Balcony

          Car

          • Car Necessary
          • Car Recommended

          Property Manager

          • VIP Luxury Villas
          • 30 Day Properties

          September 2026

          SMTWTFS
          19$1,000
          20$1,00021$1,00022$1,00023$1,00024$1,00025$1,00026$1,000
          27$1,00028$1,00029$1,00030$1,000

          October 2026

          SMTWTFS
          01$1,00002$1,00003$1,000
          04$1,00005$1,00006$1,00007$1,00008$1,00009$1,00010$1,000
          11$1,00012$1,00013$1,00014$1,00015$1,00016$1,00017$1,000
          18$1,00019$1,00020$1,00021$1,00022$1,00023$1,00024$1,000
          25$1,00026$1,00027$1,00028$1,00029$1,00030$1,00031$1,000

          November 2026

          SMTWTFS
          01$1,00002$1,00003$1,00004$1,00005$1,00006$1,00007$1,000
          08$1,00009$1,00010$1,00011$1,00012$1,00013$1,00014$1,000
          15$1,16616$1,16617$1,16618$1,16619$1,16620$1,16621$1,166
          22$1,16623$1,16624$1,16625$1,16626$1,16627$1,16628$1,166
          29$1,16630$1,166

          December 2026

          SMTWTFS
          01$1,66702$1,66703$1,66704$1,66705$1,667
          06$1,66707$1,66708$1,66709$1,66710$1,66711$1,66712$1,667
          13$1,66714$1,66715$1,66716$1,66717$1,66718$1,66719$1,667
          20$1,66721$1,66722$1,66723$1,66724$1,66725$1,66726$1,667
          27$1,66728$1,66729$1,66730$1,66731$1,667

          January 2027

          SMTWTFS
          01$1,66702$1,667
          03$1,66704$1,66705$1,66706$1,33307$1,33308$1,33309$1,333
          10$1,33311$1,33312$1,33313$1,33314$1,33315$1,33316$1,333
          17$1,33318$1,33319$1,33320$1,33321$1,33322$1,33323$1,333
          24$1,33325$1,33326$1,33327$1,33328$1,33329$1,33330$1,333
          31$1,333

          February 2027

          SMTWTFS
          01$1,33302$1,33303$1,33304$1,33305$1,33306$1,333
          07$1,33308$1,33309$1,33310$1,33311$1,33312$1,33313$1,333
          14$1,33315$1,33316$1,33317$1,33318$1,33319$1,33320$1,333
          21$1,33322$1,33323$1,33324$1,33325$1,33326$1,33327$1,333
          28$1,333

          March 2027

          SMTWTFS
          01$1,33302$1,33303$1,33304$1,33305$1,33306$1,333
          07$1,33308$1,33309$1,33310$1,33311$1,33312$1,33313$1,333
          14$1,33315$1,41616$1,41617$1,41618$1,41619$1,41620$1,416
          21$1,41622$1,41623$1,41624$1,41625$1,41626$1,41627$1,416
          28$1,41629$1,41630$1,41631$1,416

          April 2027

          SMTWTFS
          01$1,41602$1,41603$1,416
          04$1,41605$1,41606$1,41607$1,41608$1,41609$1,41610$1,416
          11$1,41612$1,41613$1,41614$1,41615$1,41616$1,41617$1,416
          18$1,41619$1,41620$1,41621$1,41622$1,41623$1,41624$1,416
          25$1,41626$1,41627$1,41628$1,41629$1,41630$1,416

          May 2027

          SMTWTFS
          01$1,416
          02$1,41603$1,41604$1,41605$1,41606$1,41607$1,41608$1,416
          09$1,41610$1,41611$1,41612$1,41613$1,41614$1,41615$1,416
          16$1,41617$1,41618$1,41619$1,41620$1,41621$1,41622$1,416
          23$1,41624$1,41625$1,41626$1,41627$1,41628$1,41629$1,416
          30$1,41631$1,416

          June 2027

          SMTWTFS
          01$1,41602$1,41603$1,41604$1,41605$1,416
          06$1,41607$1,41608$1,41609$1,41610$1,41611$1,41612$1,416
          13$1,41614$1,41615$1,41616$1,41617$1,41618$1,41619$1,416
          20$1,41621$1,41622$1,41623$1,41624$1,41625$1,41626$1,416
          27$1,41628$1,41629$1,41630$1,416

          July 2027

          SMTWTFS
          01$1,41602$1,41603$1,416
          04$1,41605$1,41606$1,41607$1,41608$1,41609$1,41610$1,416
          11$1,41612$1,41613$1,41614$1,41615$1,41616$1,41617$1,416
          18$1,41619$1,41620$1,41621$1,41622$1,41623$1,41624$1,416
          25$1,41626$1,41627$1,41628$1,41629$1,41630$1,41631$1,416

          August 2027

          SMTWTFS
          01$1,41602$1,41603$1,41604$1,41605$1,41606$1,41607$1,416
          08$1,41609$1,41610$1,41611$1,41612$1,41613$1,41614$1,416
          15$1,41616$1,41617$1,41618$1,41619$1,41620$1,41621$1,416
          22$1,41623$1,41624$1,41625$1,41626$1,41627$1,41628$1,416
          29$1,41630$1,41631$1,416

          September 2027

          SMTWTFS
          01$1,16602$1,16603$1,16604$1,166
          05$1,16606$1,16607$1,16608$1,16609$1,16610$1,16611$1,166
          12$1,16613$1,16614$1,16615$1,16616$1,16617$1,16618$1,166
          19$1,16620$1,16621$1,16622$1,16623$1,16624$1,16625$1,166
          26$1,16627$1,16628$1,16629$1,16630$1,166

          October 2027

          SMTWTFS
          01$1,16602$1,166
          03$1,16604$1,16605$1,16606$1,16607$1,16608$1,16609$1,166
          10$1,16611$1,16612$1,16613$1,16614$1,16615$1,16616$1,166
          17$1,16618$1,16619$1,16620$1,16621$1,16622$1,16623$1,166
          24$1,16625$1,16626$1,16627$1,16628$1,16629$1,16630$1,166
          31$1,166

          November 2027

          SMTWTFS
          01$1,16602$1,16603$1,16604$1,16605$1,16606$1,166
          07$1,16608$1,16609$1,16610$1,16611$1,16612$1,16613$1,166
          14$1,16615$1,50016$1,50017$1,50018$1,50019$1,50020$1,500
          21$1,50022$1,50023$1,50024$1,50025$1,50026$1,50027$1,500
          28$1,50029$1,50030$1,500

          December 2027

          SMTWTFS
          01$1,33302$1,33303$1,33304$1,333
          05$1,33306$1,33307$1,33308$1,33309$1,33310$1,33311$1,333
          12$1,33313$1,33314$1,33315$1,83316$1,83317$1,83318$1,833
          19$1,83320$1,83321$1,83322$1,83323$1,83324$1,83325$1,833
          26$1,83327$1,83328$1,83329$1,83330$1,83331$1,833

          January 2028

          SMTWTFS
          01$1,833
          02$1,83303$1,83304$1,83305$1,33306$1,33307$1,33308$1,333
          09$1,33310$1,33311$1,33312$1,33313$1,33314$1,33315$1,333
          16$1,33317$1,33318$1,33319$1,33320$1,33321$1,33322$1,333
          23$1,33324$1,33325$1,33326$1,33327$1,33328$1,33329$1,333
          30$1,33331$1,333

          February 2028

          SMTWTFS
          01$1,33302$1,33303$1,33304$1,33305$1,333
          06$1,33307$1,33308$1,33309$1,33310$1,33311$1,33312$1,333
          13$1,33314$1,33315$1,33316$1,33317$1,33318$1,33319$1,333
          20$1,33321$1,33322$1,33323$1,33324$1,33325$1,33326$1,333
          27$1,33328$1,33329$1,333

          March 2028

          SMTWTFS
          01$1,33302$1,33303$1,33304$1,333
          05$1,33306$1,33307$1,33308$1,33309$1,33310$1,33311$1,333
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