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Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi

Family-friendly holiday home in Honolulu

Photo gallery for Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi

Exterior
Let the crystal clear pool sooth your soul
Poolside fire pit where to gather with friends at night
Get comfortable, relax, and enjoy the gentle trade winds
Enjoy outdoor dining for 8 on the deck with pool views

Reviews

9.8 out of 10
Exceptional
5 bedrooms4 bathroomsSleeps 104200 sq ft

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Pool
  • Barbecue grill
  • Air conditioning

Explore the area

View in a map
Honolulu, HI
  • Place, Diamond Head State Monument
    ‪10 min walk‬
  • Place, Kahala Beach
    ‪15 min walk‬
  • Place, Diamond Head
    ‪7 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 Queen Bed

Guest Bedroom 4

1 Queen Bed

Guest Bedroom 5

1 Single Bed and 1 Double Bed

Primary Bedroom

1 King Bed

4 bathrooms

Guest Bathroom 2

Guest Bathroom 3

Guest Bathroom 4

Primary Bedroom Ensuite

Spaces

Kitchen
Balcony
Garden
Dining area

About this property

Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi

Set beneath the slopes of Diamond Head on Oahu’s iconic Gold Coast, Hale Le‘ahi by Gather is a grand three-story plantation-style estate that captures the timeless beauty of old Hawai‘i with modern luxury. This 5-bedroom, 4-bathroom retreat spans over 4,200 sq. ft. and welcomes up to 10 guests to relax, entertain, and experience the island lifestyle at its finest.

What You’ll Love About Hale Le‘ahi by Gather
• Expansive private pool surrounded by lush tropical landscaping
• Outdoor dining and lounge areas with mountain and garden views
• Elegant plantation architecture with breezy open-air design
• Gourmet kitchen with premium appliances, breakfast bar, and formal dining for 8
• Game room and bar with pool and ping-pong table for evening fun
• Five bedrooms, each with A/C and ceiling fans for year-round comfort
• Peaceful Diamond Head neighborhood minutes from beaches and Waikiki

Living & Dining
Step through the entryway into a bright and spacious home filled with natural light and the island’s cooling trade winds. The open-concept living room is tastefully furnished with comfortable seating, a large TV, and access to the shaded lanai overlooking the pool. The adjoining dining area offers seating for eight and connects seamlessly to the gourmet kitchen, featuring high-end stainless steel appliances, a wine cooler, and a central island with counter seating.

Downstairs, guests can gather in the game room, complete with a pool table that converts to ping-pong, dartboard, bar area, and lounge with TV — perfect for relaxed evenings or friendly competitions.

Outdoor Oasis
Step outside to your private tropical haven. The large pool is surrounded by sun loungers, shaded seating, and vibrant island foliage offering total privacy. Dine al fresco on the raised deck with seating for eight, or enjoy morning coffee on the lanai while the island awakens around you. As evening falls, gather by the fire pit under the stars and take in the peaceful sound of swaying palms.

Sleeping Quarters
• Primary Suite – California King bed, private lanai with garden and ocean views, ensuite bath with soaking tub, dual vanities, and marble accents.
• Guest Suite 2 – King bed, daybed for lounging or additional sleeping, kitchenette, and direct pool access with garden views.
• Guest Suite 3 – Queen bed, desk, deck access, and nearby full bath with walk-in shower.
• Guest Suite 4 – Queen bed, desk, and shared access to deck and full bath.
• Guest Suite 5 – One Full bed and one Twin bed, ideal for children or singles, with access to a nearby full bath.

Each bedroom is designed for comfort and privacy, featuring air conditioning, ceiling fans, and tasteful island décor.

Extras
Amenities include high-speed Wi-Fi, laundry facilities, multiple smart TVs, and driveway parking for two vehicles.

Neighborhood & Location
Located on the lower slopes of Diamond Head, Hale Le‘ahi offers quick access to Oahu’s best beaches and attractions. Stroll to Cromwell’s Beach or drive just minutes to Waikiki, Kahala Beach, and Diamond Head Beach. Nearby, you’ll find scenic hikes, shopping at Kahala Mall, and a wide range of dining options — from local favorites to world-class restaurants.

Good to Know
• Monthly rental only; full-month rate applies regardless of stay length
• Utility fee of $1,500/month applies to all stays of 21 days or more
• Driveway parking for two cars; street parking available
• HI Tax ID: TA-021-803-2128-01
• TMK: 1350020240000000

Your Island Story Awaits
From sunrise swims in your private pool to sunset gatherings under the palms, Hale Le‘ahi by Gather offers a serene escape where the warmth of Aloha meets timeless Hawaiian elegance — perfect for extended stays with family and friends.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space

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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
Safety features at this property include a fire extinguisher and a first aid kit
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 TA-021-803-2128-01, GE-021-803-2128-01, 1350020240000

About the area

Honolulu

Located by the sea, this holiday home is in Kahala, a neighbourhood in Honolulu. International Market Place and Royal Hawaiian Center 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 Diamond Head. Travelling with kids? Consider Honolulu Zoo, or check out an event or a game at Clarence T.C. Ching Athletics Complex. Discover the area's water adventures with scuba diving and fishing nearby, or enjoy the great outdoors with hiking/biking trails and horse riding.
Map
Honolulu, HI

What's nearby

  • Diamond Head Beach Park - 8 min walk - 0.8 km
  • Diamond Head State Monument - 10 min walk - 0.9 km
  • Kahala Beach - 15 min walk - 1.3 km
  • Kahala Mall - 3 min drive - 2.3 km
  • Diamond Head - 7 min drive - 1.9 km

Getting around

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

Restaurants

  • ‪Starbucks - ‬4 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Pizza Hut - ‬3 min drive
  • ‪KuruKuru Sushi - Kahala Mall - ‬3 min drive
  • ‪Fort Ruger Market - ‬3 min drive

Frequently asked questions

Is Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi pet-friendly?

No, pets are not allowed at this property.

How much is parking at Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi?

On-site parking is available at the property.

What time is check-in at Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi?

Check-in begins at 4:00 PM.

What time is check-out at Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi?

Checkout is at 10:00 AM.

Where is Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi located?

This family-friendly Honolulu holiday home is located by the sea, within 1 mi (2 km) of Diamond Head State Monument and Kahala Beach. Waikiki Beach and Honolulu Zoo are also within 3 miles (5 km).

About the host

Hosted by Gather Vacations

Host profile image
Gather with us! Gather Vacation Rentals is the leading luxury property manager in the US. Gather was founded in 2005 and our properties reflect our high standards of excellence. With over 400 professionally managed luxury homes available for vacation rentals, we are committed to making sure that our vacation clients experience the very best in quality, delivery, and outstanding service

Our Vacation Rental Management Team reflects our high standards of excellence. With over 400 professionally managed luxury homes available for vacation rentals throughout the US, we are committed to ensuring our vacation clients experience the very best in quality, delivery, and outstanding service.

Active Member of:
- (VRMA) Vacation Rental Managers Association
- (NAR) National Association of Realtors

Languages:

English

Premier Host

They consistently provide great experiences for their guests