Hale Le'ahi: Diamond Head Luxury Home with Pool, AC, Lanai and Close to Waikiki

Hale Le'ahi is a grand three-story plantation-style estate nestled on the lower slopes of Diamond Head, offering a timeless Hawaiian retreat just minutes from Kahala and Waikiki. This five-bedroom, four-bathroom home sleeps up to ten guests and features a large outdoor pool, tropical gardens, and expansive lanais for relaxing or dining al fresco. Inside, elegant vintage charm meets modern comfort with a gourmet kitchen, open-air living spaces, and a game room with billiards, ping-pong, and a bar lounge. The primary suite boasts ocean and mountain views, a private lanai, and a spa-like bath. With easy access to Cromwell's Beach, Diamond Head Crater, and Honolulu's vibrant attractions, Hale Le'ahi offers the perfect blend of island elegance and authentic aloha spirit.

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$950/night
9.8/10 28 reviews
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Property Description

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.

Registration Number: TA-021-803-2128-01 · GE-021-803-2128-01

ℹ️ Frequently Asked Questions

Where is this vacation rental located?
  • City: Waikiki (postal 96816) Hawaii

Nearby highlights:

  • Location: Honolulu, HI, United States
  • Near a health or beauty spa
  • Near a zoo
  • Near the sea
How many bedrooms and bathrooms does it have?

5 bedrooms, 4 bathrooms

How many guests can it sleep?

Sleeps up to 10 guests.

What amenities are available?
  • Private vacation home
  • Unit size: 4200 sq ft (390 sq m)
  • 5 bedrooms
  • Bed sheets provided
  • Day bed
  • 4 bathrooms
  • Hair dryer
  • Air conditioning
  • Internet access
  • Coffee/tea maker
  • Cookware/dishes/utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster
  • Laundry facilities
  • Washing machine and dryer
  • Private pool
  • Lanai / balcony
  • Barbecue grill
  • Fenced yard
  • Firepit
  • Garden
  • Onsite parking
  • Popular: A/C
  • Arcade
  • BBQ grill
  • Dryer
  • Extra Bed
  • Free Parking
  • Kitchen
  • Laundry
  • No Smoking
  • Outdoor Space
  • Pool
  • Tennis Court
  • Toys
  • Tv
  • Washer
What should I know about check-in?
  • Check-in starts at 4:00 PM
  • Check-out before before 10:00 am
  • Minimum check-in age: 21
  • Onsite parties or group events are strictly prohibited
  • Property Registration Number TA-021-803-2128-01

House rules:

  • Pets not allowed, Children are welcome., Onsite parties or group events are strictly prohibited
What are popular things to do nearby and on Oahu?
  • Cycling
  • Fishing
  • Golfing on site
  • Hiking
  • Hiking/biking trails
  • Horse riding
  • Scuba diving
  • Tennis on site

Popular Oahu Activities include luaus, snorkeling, Pearl Harbor tours, and catamaran cruises.

Do I need a rental car on Oahu, and what about parking?
  • Onsite parking

Car is optional in Waikiki/Honolulu – consider a rental car only for day trips (North Shore, East Oahu, etc.).

What kind of rental is this?

This is a home rental.


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