Diamond Head Grand Escape

Honolulu, HI 5 Bedrooms Vacation Rental

5 Beds 5 Full Baths, and 1 Half Bath Sleeps 10
Step onto your lanai to take in uninterrupted ocean vistas, the perfect spot for coffee or cocktails. Gather with family in the light-filled living space, where glass walls frame sweeping Pacific views.
Gather with family in the light-filled living space, where glass walls frame sweeping Pacific views.

Show All Photos

Rooms

  • bed icon

    Bedroom # 1

    Primary Bedroom

    1 King

  • bed icon

    Bedroom # 2

    Guest Bedroom 2

    1 King

  • bed icon

    Bedroom # 3

    Guest Bedroom 3

    1 King

  • bed icon

    Bedroom # 4

    Guest Bedroom 4

    1 King

  • bed icon

    Bedroom # 5

    Guest Bedroom 5

    1 King

5 Beds 5 Baths Sleeps 10

Amenities

Private pool
Air conditioning
Beach Front
Hot Tub

Description

This award-winning oceanfront residence, Diamond Head Grand Escape, offers a rare opportunity to experience contemporary Hawaiian living in one of Honolulu’s most coveted enclaves. Set directly on the sand within the exclusive Cove area of Diamond Head, this home is one of only 27 with private beachfront access. With 7,324 square feet of refined interiors, five ensuite bedrooms, and spectacular outdoor spaces, it is perfectly curated for families, friends, and guests seeking a true sense of place.

What You’ll Love About Diamond Head Grand Escape
• Direct beachfront location in Diamond Head Cove, steps to Cromwell’s surf break
• Infinity-edge pool and spa with tiki torch ambiance
• Dramatic floating glass staircase and modern wine closet
• State-of-the-art automation, elevator, and whole-home audio
• Outdoor lounge with full kitchen, professional landscaping, and surfboard storage
• Primary bedroom features an ensuite with both his and hers bathrooms

Living & Dining
Walls of glass frame sweeping Pacific views, filling the great room with natural light. Elegant design elements include a floating staircase with glass railings, soaring ceilings, and handcrafted finishes. Multiple seating areas invite conversation and relaxation, while the dining space connects seamlessly with both the chef’s kitchen and lanai for effortless indoor-outdoor flow.

Chef-Ready Kitchen
The gourmet kitchen is outfitted with professional-grade appliances, marble island countertops, and custom cabinetry. A butler’s pantry provides additional storage and prep space, ideal for private chefs or group entertaining.

Outdoor Oasis
Step outside to an infinity-edge pool and spa framed by tiki torches, swaying palms, and the sound of waves. The outdoor lounge features a full kitchen, dining space, and comfortable seating designed for gatherings. Professional landscaping enhances privacy, while direct access to the sand makes the ocean your backyard.

Sleeping Quarters
• Primary Suite – King bed, primary ensuite including both his & hers bathrooms, steam shower, ocean & garden views, central AC, ceiling fan
• Guest Suite 2 – King bed, ensuite bath, central AC
• Guest Suite 3 – King bed, ensuite bath, central AC
• Guest Suite 4 – King bed, ensuite bath, central AC
• Guest Suite 5 – King bed, ensuite bath, central AC
• Powder Room – Half bath

Extras
A glass-enclosed wine closet, home office, library, and game room provide versatility for work and play. The residence also includes whole-home automation, a security system, elevator, and audio throughout. Surfboard and outrigger storage are conveniently located steps from the sand.

Nearby
Walk to Waikiki’s vibrant dining and nightlife or hike the iconic Diamond Head crater. The surf break at Cromwell’s is just offshore, while a short drive brings you to Ala Moana shopping, cultural venues, and championship golf.

Good to Know
* This home is available exclusively for 30-day minimum stays. The property is also currently for sale; a marketing disclaimer will be provided at booking. Occupancy is exclusive for your rental period. TAT and applicable taxes apply.
* TMK: 310390060000
* TA-085-937-5616-01

Reserve your dates now at Diamond Head Grand Escape and experience an oceanfront lifestyle defined by elegance, comfort, and design.

Room

Beds


Primary Bedroom

King (1)

Ensuite Bathroom, Ocean View, Garden View, Central AC, Ceiling Fan


Guest Bedroom 2

King (1)

Ensuite Bathroom, Central AC


Guest Bedroom 3

King (1)

Ensuite Bathroom, Central AC


Guest Bedroom 4

King (1)

Ensuite Bathroom, Central AC


Guest Bedroom 5

King (1)

Ensuite Bathroom, Central AC


Primary Bedroom Ensuite

full bathroom


Guest Full Bathroom 2

full bathroom


Guest Full Bathroom 3

full bathroom


Guest Full Bathroom 4

full bathroom


Guest Full Bathroom 5

full bathroom


Powder Room 1

half bathroom

Nearby Activities

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

Kitchen and Dining

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

Amenities

  • Dryer
  • Essentials
  • Ethernet Connection
  • Extra Pillows And Blankets
  • Garage
  • Hair Dryer
  • Iron
  • Keypad
  • Linens
  • Parking space
  • Private Entrance
  • Shampoo
  • Washer
  • Wifi/Internet

Suitability

  • Air Conditioning
  • Bath Tub
  • Ceiling fans
  • Children Welcome
  • Free Parking
  • Hot Water
  • Smoking Not Allowed
  • Suitable for Elderly

Emergency

  • Emergency Fire Contact
  • Emergency Police Contact

Cleanliness

  • 24Hr Check-In

Safety Features

  • Deadbolt Lock
  • Fire Extinguisher
  • Outdoor Lighting
  • Security Cameras
  • Smoke Detector

Entertainment

  • Game room
  • Laptop Friendly
  • Pool Table
  • Satellite or Cable TV
  • Smart TV
  • Sonos Audio System
  • Speaker System
  • Television

Pool/Spa

  • Heated Pool
  • Hot Tub
  • Private Pool

Internal Amenities

  • Additional Bedding
  • Beach Chairs
  • Beach Towels
  • Boogie Boards
  • Stair Gates

Outdoor Amenities

  • Beach Umbrella
  • Cooler - Ice Chest
  • Garden
  • Insulated Cooler Bag
  • Lanai/Balcony
  • Outdoor Kitchen
  • Outdoor Shower
  • Outdoor seating
  • Private yard

Themes

  • Family
  • Luxury
  • Romantic

Car

  • Car Recommended

Location/Property Types

  • Beach Front
  • Garden View
  • Ocean Front
  • Popular Town
  • Private / Secluded
  • Walk to Shops / Restaurants
  • Waterfront

Property Manager

  • Claudia Evenschor

Promos

  • Holidays

promos

  • 2026Spring15

Leave a review:

Please Rate your stay

Comments

Personal Information:

Thank you for submitting your review. It will be processed shortly!

No Reviews.

June 2026

S M T W T F S
  01 02 03 04 05 06
07 08 09
$4,500
10
$4,500
11
$4,500
12
$4,500
13
$4,500
14
$4,500
15
$4,500
16
$4,500
17
$4,500
18
$4,500
19
$4,500
20
$4,500
21
$4,500
22
$4,500
23
$4,500
24
$4,500
25
$4,500
26
$4,500
27
$4,500
28
$4,500
29
$4,500
30
$4,500
       

July 2026

S M T W T F S
      01
$4,500
02
$4,500
03
$4,500
04
$4,500
05
$4,500
06
$4,500
07
$4,500
08
$4,500
09
$4,500
10
$4,500
11
$4,500
12
$4,500
13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 31  

August 2026

S M T W T F S
            01
02 03 04 05 06 07 08
09 10 11
$4,500
12
$4,500
13
$4,500
14
$4,500
15
$4,500
16
$4,500
17
$4,500
18
$4,500
19
$4,500
20
$4,500
21
$4,500
22
$4,500
23
$4,500
24
$4,500
25
$4,500
26
$4,500
27
$4,500
28
$4,500
29
$4,500
30
$4,500
31
$4,500
         

September 2026

S M T W T F S
    01
$2,835
02
$2,835
03
$2,835
04
$2,835
05
$2,835
06
$2,835
07
$2,835
08
$2,835
09
$2,835
10
$2,835
11
$2,835
12
$2,835
13
$2,835
14
$2,835
15
$2,835
16
$2,835
17
$2,835
18
$2,835
19
$2,835
20
$2,835
21
$2,835
22
$2,835
23
$2,835
24
$2,835
25
$2,835
26
$2,835
27
$2,835
28
$2,835
29
$2,835
30
$2,835
     

October 2026

S M T W T F S
        01
$2,835
02
$2,835
03
$2,835
04
$2,835
05
$2,835
06
$2,835
07
$2,835
08
$2,835
09
$2,835
10
$2,835
11
$2,835
12
$2,835
13
$2,835
14
$2,835
15
$2,835
16
$2,835
17
$2,835
18
$2,835
19
$2,835
20
$2,835
21
$2,835
22
$2,835
23
$2,835
24
$2,835
25
$2,835
26
$2,835
27
$2,835
28
$2,835
29
$2,835
30
$2,835
31
$2,835

November 2026

S M T W T F S
01
$4,000
02
$4,000
03
$4,000
04
$4,000
05
$4,000
06
$4,000
07
$4,000
08
$4,000
09
$4,000
10
$4,000
11
$4,000
12
$4,000
13
$4,000
14
$4,000
15
$4,000
16
$4,000
17
$4,000
18
$4,000
19
$4,000
20
$4,000
21
$4,000
22
$4,000
23
$4,000
24
$4,000
25
$4,000
26
$4,000
27
$4,000
28
$4,000
29
$4,000
30
$4,000
         

December 2026

S M T W T F S
    01
$5,000
02
$5,000
03
$5,000
04
$5,000
05
$5,000
06
$5,000
07
$5,000
08
$5,000
09
$5,000
10
$5,000
11
$5,000
12
$5,000
13
$5,000
14
$5,000
15
$5,000
16
$5,000
17
$5,000
18
$5,000
19
$5,000
20
$5,000
21
$5,000
22
$5,000
23
$5,000
24
$5,000
25
$5,000
26
$5,000
27
$5,000
28
$5,000
29
$5,000
30
$5,000
31
$5,000
   

January 2027

S M T W T F S
          01
$5,000
02
$5,000
03
$5,000
04
$8,000
05 06 07 08 09
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            

February 2027

S M T W T F S
  01 02 03 04 05 06
07 08 09 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28            

March 2027

S M T W T F S
  01 02 03 04 05
$4,000
06
$4,000
07 08 09 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
$4,000
28
$4,000
29
$4,000
30
$4,000
31
$4,000
     

April 2027

S M T W T F S
        01
$4,000
02
$4,000
03
$4,000
04
$4,000
05
$4,000
06
$4,000
07
$4,000
08
$4,000
09
$4,000
10
$4,000
11
$4,000
12
$4,000
13
$4,000
14
$4,000
15
$4,000
16
$4,000
17
$4,000
18
$4,000
19
$4,000
20
$4,000
21
$4,000
22
$4,000
23
$4,000
24
$4,000
25
$4,000
26
$4,000
27
$4,000
28
$4,000
29
$4,000
30
$4,000
 

May 2027

S M T W T F S
            01
$4,000
02
$4,000
03
$4,000
04
$4,000
05
$4,000
06
$4,000
07
$4,000
08
$4,000
09
$4,000
10
$4,000
11
$4,000
12
$4,000
13
$4,000
14
$4,000
15
$4,000
16
$4,000
17
$4,000
18
$4,000
19
$4,000
20
$4,000
21
$4,000
22
$4,000
23
$4,000
24
$4,000
25
$4,000
26
$4,000
27
$4,000
28
$4,000
29
$4,000
30
$4,000
31
$4,000
         
    Available     Unavailable  Check-In Only  Check-Out Only

Adults

Ages 18 or above

Children

Ages 2-17

Infants

Under 2

Pets

Bringing your pets?

Request Submitted!

Starting May 7, 2025, a REAL ID or passport is required for Domestic U.S. flights—plan ahead! Learn more HERE

Terms & Conditions