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Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi
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Reviews
9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms4 bathroomsSleeps 104200 sq ft
Popular amenities
Explore the area

Honolulu, HI
- Place, Diamond Head Beach Park8 min walk
- Place, Diamond Head State Monument10 min walk
- Place, Kahala Beach15 min walk
- Airport, Honolulu, HI (HNL-Daniel K. Inouye Intl.)22 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Guest Bedroom 2 (Lower pool level)
1 King Bed
Guest Bedroom 3 (main level)
1 Queen Bed
Guest Bedroom 4 (main level)
1 Queen Bed
Guest Bedroom 5 (Upper Primary level)
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.
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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- Ocean view
- Pool
- Hot tub
- Kitchen
House Rules
Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
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. Royal Hawaiian Center and Waikiki Beach Walk are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Diamond Head and Waikiki Beach. 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 and horse riding.

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
Restaurants
- Starbucks - 4 min drive
- McDonald's - 3 min drive
- California Pizza Kitchen - 4 min drive
- Pizza Hut - 3 min drive
- KuruKuru Sushi - Kahala Mall - 3 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
29 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 10 nights in Mar 2023
10/10 Excellent
Kyle H.
16 Oct, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Home in a Great Neighborhood
Kyle H.
Stayed 8 nights in Oct 2022
10/10 Excellent
Jasmine M.
5 Sept, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best Oahu stay!
Jasmine M.
Stayed 8 nights in Aug 2021
10/10 Excellent
Nancy P.
1 Mar, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
a Week in Paradise
Nancy P.
Stayed 7 nights in Feb 2020
10/10 Excellent
Todd T.
2 Jul, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
First Class
Todd T.
Stayed 7 nights in Jun 2019
10/10 Excellent
Debra O.
13 Jul, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous house and great property management
Debra O.
Stayed 8 nights in Jun 2021
10/10 Excellent
Sarah C., San Francisco, CA United States
20 Mar, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful house in great neighborhood
Sarah C.
Stayed 7 nights in Feb 2022
10/10 Excellent
Cheo C.
6 Jan, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
What an amazing house!
Cheo C.
Stayed 14 nights in Dec 2021
10/10 Excellent
Joslin C., Bingham Farms, MI
27 Feb, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lise was so helpful from the moment we connected. We thoroughly enjoyed our stay!
Joslin C.
Stayed 7 nights in Feb 2020
10/10 Excellent
Scott C.
10 Jan, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
What an exceptional place
Scott C.
Stayed 7 nights in Dec 2019
10/10 Excellent
Verified traveller
10 Dec, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful week with family
Verified traveller
Stayed 7 nights in Nov 2019
10/10 Excellent
Denise V.
6 Dec, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best ever!!!
Denise V.
Stayed 6 nights in Nov 2019
8/10 Good
Lynette H.
27 Sept, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful fully equipped large family home with terrific pool.
Lynette H.
Stayed 7 nights in Sep 2019
8/10 Good
Latonia P.
26 Sept, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoyed My Visit...Mostly
Latonia P.
Stayed 7 nights in Sep 2019
10/10 Excellent
David S.
8 Sept, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect family getaway
David S.
Stayed 8 nights in Aug 2019
10/10 Excellent
Ronna S.
3 Jul, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved this property. The pictures in the listing were exactly what the home was!
Ronna S.
Stayed 7 nights in Jun 2019
10/10 Excellent
Stacey M.
18 Jun, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
If you are even thinking about staying here you have to!
Stacey M.
Stayed 7 nights in Jun 2019
10/10 Excellent
Kiva H.
10 May, 2019
Amazing house in a great location
Kiva H.
Stayed 6 nights in Apr 2019
10/10 Excellent
Satinder K.
28 Apr, 2019
Wonderful
Satinder K.
Stayed 7 nights in Apr 2019
10/10 Excellent
Linda S.
8 Feb, 2019
Perfect for the Family
Linda S.
Stayed 7 nights in Jul 2018
10/10 Excellent
Christopher L.
8 Feb, 2019
Absolute paradise, making the vacation even better!
Christopher L.
Stayed 7 nights in May 2018
10/10 Excellent
Tamara T.
31 Jan, 2019
Beautiful, spacious and comfy!
Tamara T.
Stayed 7 nights in Jan 2019
10/10 Excellent
Sanford W., Baltimore, MD / Yokohama, Japan
11 Jan, 2019
Great family holiday!
Sanford W.
Stayed 7 nights in Dec 2018
10/10 Excellent
terry b.
10 Nov, 2018
Impeccable oasis
terry b.
Stayed 7 nights in Oct 2018
10/10 Excellent
Kathy A B.
6 Oct, 2018
Beautiful, luxurious vacation home! Wonderful experience!
Kathy A B.
Stayed 5 nights in Sep 2018
About the host
Hosted by Gather Vacations
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
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
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