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Five-Bedroom Estate Near Diamond Head

Holiday home with private pool, near Waikiki Beach

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Private resort-style pool set below the main lanai, offering layered privacy and tropical surroundings.
Unwind in the tucked-away Jacuzzi and pool area, designed for quiet relaxation and seclusion.
A covered lanai extends the living space outdoors, perfect for dining and lounging with coastal views.
A discreet, garden-lined entrance welcomes you into this private Diamond Head estate.
Light-filled living space blending island elegance with modern design and views toward the coastline.
5 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Ocean view
  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer

Explore the area

View map
Honolulu, HI
  • Place, Diamond Head State Monument
    ‪2 min walk‬
  • Place, Diamond Head
    ‪14 min walk‬
  • Place, Waikiki Beach
    ‪4 min drive‬
  • Airport, Honolulu, HI (HNL-Daniel K. Inouye Intl.)
    ‪22 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Guest Bedroom 2

1 King Bed

Guest Bedroom 3

1 King Bed

Ilima Bungalow

1 King Bed

Plumeria Bungalow

1 King Bed

Primary Bedroom

1 King Bed

4 bathrooms

Guest Bathroom

Ilima Bungalow Ensuite

Plumeria Bungalow Ensuite

Primary Bedroom Ensuite

Spaces

Kitchen
Balcony
Garden
Dining area

About this property

Five-Bedroom Estate Near Diamond Head

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.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number 310380140000, TA-213-293-6704-01, GE-213-293-6704-01

We should mention

A car is required for transport to and from this property

About the area

Honolulu

Kahala, a neighbourhood in Honolulu, is home to this holiday home. Royal Hawaiian Center and International Market Place are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Waikiki Beach and Kaimana Beach. Looking to enjoy an event or a game while in town? See what's happening at Neal S. Blaisdell Center or Aloha Stadium. Discover the area's water adventures with scuba diving and fishing nearby, or enjoy the great outdoors with horse riding and cycling.
Map
Honolulu, HI

What's nearby

  • Diamond Head Beach Park - 1 min walk - 0.0 km
  • Diamond Head State Monument - 2 min walk - 0.2 km
  • Diamond Head - 14 min walk - 1.2 km
  • Queen Kapiʻolani Regional Park - 2 min drive - 2.3 km
  • Waikiki Beach - 4 min drive - 3.0 km

Getting around

  • Hālaulani / Leeward Community College Station - 28 min drive
  • Honolulu, HI (HNL-Daniel K. Inouye Intl.) - 27 min drive

Restaurants

  • ‪Diamond Head Market & Grill - ‬5 min drive
  • ‪Fort Ruger Market - ‬3 min drive
  • ‪Hau Tree Lanai Restaurant - ‬4 min drive
  • ‪Aloha Pineapple Cafe - ‬4 min drive
  • ‪Arden Waikiki - ‬3 min drive

Frequently asked questions

Is Five-Bedroom Estate Near Diamond Head pet-friendly?

No, pets are not allowed at this property.

How much is parking at Five-Bedroom Estate Near Diamond Head?

On-site parking is available at the property.

What time is check-in at Five-Bedroom Estate Near Diamond Head?

Check-in begins at 4:00 PM.

What time is check-out at Five-Bedroom Estate Near Diamond Head?

Checkout is at 10:00 AM.

Where is Five-Bedroom Estate Near Diamond Head located?

Located in Kahala, this holiday home is steps from Diamond Head State Monument and within 3 mi (5 km) of Waikiki Beach and Honolulu Zoo. International Market Place and Royal Hawaiian Center are also within 3 miles (5 km).

About the host

Hosted by Gather Vacations

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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