Lanikai Hillside Estate
Kailua, HI 7 Bedrooms Vacation Rental
Show All Photos
Rooms
rooms
-
Bedroom # 1
Primary Bedroom
1 King
-
Bedroom # 2
King Bedroom
1 King
-
Bedroom # 3
Twin Bedroom
1 Twin
-
Bedroom # 4
Triple Bedroom
1 Double, 2 Twin,
-
Bedroom # 5
Guest House Suite
1 Cal King
-
Bedroom # 6
Piano Room/Study
2 Twin
-
Bedroom # 7
Housekeeper Room
1 Double
Amenities
Description
What You’ll Love About Lanikai Hillside Estate by Gather
• Unparalleled ocean vistas from nearly every room and the infinity-edge pool
• Private rooftop retreat with jacuzzi, fire pit, and lounge seating for sunrise, sunset & stargazing
• Resort-style amenities including media room/home theater, gym, sauna, office, and multiple lanais
• Exclusive shoreline access for effortless days on Lanikai’s soft white sand
• Central A/C and a refined modern aesthetic that frames the natural beauty outside
Living & Dining
On the main level, expansive living and dining areas open wide to the lanai and infinity pool where the horizon meets the sea. Clean-lined furnishings, warm textures, and artful lighting set a tranquil yet elevated tone. The indoor dining area flows easily to the outdoor pavilion, making relaxed family dinners and celebratory feasts equally effortless.
Chef-Ready Kitchen
A contemporary, fully equipped kitchen anchors the home’s social heart with generous island prep space, sleek cabinetry, and ocean views that turn cooking into a pleasure. Whether you’re preparing a casual brunch or collaborating with a private chef, the layout supports easy entertaining.
Outdoor Oasis
The estate’s grounds are designed for unhurried island days. Lounge beside the infinity pool as it visually blends into the turquoise bay. Multiple lanais offer both sun and shade, while a BBQ zone and dining pavilion invite al fresco gatherings. Ascend to the rooftop deck to soak in the jacuzzi, cozy up by the fire pit, and take in moonrise over the Mokulua Islets.
Sleeping Quarters
• Primary Suite – Oversized lanai, panoramic ocean view, spa-like Agape ensuite, walk-in closet
• Guest Bedroom 2 – Ocean view, ensuite bath
• Guest Bedroom 3 – Mountain view, ensuite bath
• Guest Bedroom 4 – View suite with shared bath
• Guest Bedroom 5 (Main Level) – Private sitting area, kitchenette, lanai access, separate entrance, ensuite bath
• Guest Bedroom 6 – Tranquil garden or mountain outlook, shared bath
• Guest Bedroom 7 – Tranquil garden or mountain outlook, shared bath
Each bedroom offers calming finishes, floor-to-ceiling glass, and thoughtful privacy so every guest wakes to a stunning natural backdrop.
Extras
Central A/C, high-speed Wi-Fi, washer & dryer, private office, media room/home theater, smart TVs with satellite/cable, speaker system, printer/scanner/fax, home gym, sauna, exclusive shoreline access path, and a private gated community setting for added peace of mind.
Resort / Community Highlights
Private gated community in Lanikai with direct access to one of the world’s most celebrated beaches.
Nearby
Kailua Town is minutes away for cafés, boutiques, and farm-to-table dining. Launch kayaks to the Mokulua Islands, snorkel calm turquoise waters, or hike the Lanikai Pillbox Trail for sweeping coastal views. HNL is the nearest major airport for convenient arrivals.
Good to Know
• This property is offered as a monthly rental
• The monthly rate applies in full regardless of the number of nights stayed
• Minimum 30-day booking period required
• Utility fee: 3,500 USD per month for stays of 21+ days
• Exclusive use for the duration of the rental period
• TAT ID: TA-053-605-3248-01
• TMK: 430010090000
Reserve your time at Lanikai Hillside Estate by Gather and experience elevated island living above one of Oahu’s most iconic beaches.
Room
Beds
Primary Bedroom
King (1)
Ocean View, Lanai / Balcony, Central A/C, Ceiling Fan, Ensuite Bathroom, King-size bed (80"x76") (US King size cm 198x234)
King Bedroom
King (1)
Mountain View, Lanai / Balcony, Central A/C, Ceiling Fan, Ensuite Bathroom, King-size bed (80"x76") (Mattress space 77.5" w x 80" )
Twin Bedroom
Twin (1)
Mountain View, Lanai / Balcony, Central A/C, Ceiling Fan, Twin-sized pull-out sofa. Bed Size: W63|D76.8|H15.7 inch (W160|D195|H40 cm)
Triple Bedroom
Double (1) Twin (2)
Lanai / Balcony, Central A/C, Ceiling Fan, Ensuite Bathroom, Twin-size bed (75"x38") with extra twin trundle (75"x38"); loft full size bed with desk/dresser [maximum 3 occupancy]
Guest House Suite
Cal King (1)
Exterior Courtyard Entrance, Ocean View, Lanai / Balcony, Split A/C, Ceiling Fan, Ensuite Bathroom, Cali King-size bed
Ensuite Bathroom - Primary Suite Bedroom 1
Extra large and luxurious bathroom with Agape Italian fixtures. Large soaking tub and stand along shower. Gorgeous Ocean Views! and doors to the lanai.
Piano Room/Study
Twin (2)
top mattress cm 86x208 - lower mattress cm 82x202
Ensuite Bathroom - Upstairs Guest Bedroom 2
Ensuite bathroom with Shower
Housekeeper Room
Double (1)
full size loft bed
Hallway Bathroom - Upstairs Guest Bedroom 3
Hallway Bathroom for Guest Bedroom 3 with Shower.
Ensuite Bathroom - Upstairs Guest Bedroom 4
Ensuite Bathroom with Shower
Ensuite Bathroom - Guest House Bedroom 5
Ensuite Bathroom with Shower
Ensuite Bathroom - Gym & Sauna
Ensuite Bath with Shower
Powder Room
Half Bath / Power Room on main level
Nearby Activities
- Cycling
- Fishing
- Golfing
- Hiking
- Horseback riding
- Museums
- Scuba diving or Snorkeling
- Shopping
- Spa and wellness
- Tennis
- Watersports
Kitchen and Dining
- BBQ
- Blender
- Coffee Maker
- Crockpot
- Dining Area
- Dishes Utensils
- Dishwasher
- Espresso Machine
- Freezer
- Kettle
- Kitchen
- Kitchen Basics
- Kitchenette
- Microwave
- Mini Fridge (Hotel Size)
- Oven
- Refrigerator
- Rice Cooker
- Stove
- Wine Fridge
Amenities
- Dryer
- Essentials
- Extra Pillows And Blankets
- Fitness Room
- Garage
- Hair Dryer
- Linens
- Parking space
- Private Entrance
- Safe
- Shampoo
- Washer
- Wifi/Internet
Cleanliness
- Self Check In / Check Out
Safety Features
- First Aid Kit
- Outdoor Lighting
- Security Cameras
- Smoke Detector
Suitability
- Air Conditioning
- Bath Tub
- Ceiling fans
- Children Welcome
- Hot Water
- Smoking Not Allowed
Entertainment
- Home theater / Theater room
- Printer/Scanner/Fax
- Satellite or Cable TV
- Smart TV
- Speaker System
- Television
Pool/Spa
- Heated Pool
- Hot Tub
- Private Pool
- Sauna
Outdoor Amenities
- Lanai/Balcony
- Outdoor Shower
Themes
- Family
- Luxury
Car
- Car Necessary
- Car Recommended
Location/Property Types
- Near Ocean
- Ocean View
- Private Gated Community
- Walk to beach
Property Manager
- 30 Day Properties
- Hawaii Luxury Homes
- Mark LeRoy Hualalai
Thank you for submitting your review. It will be processed shortly!
No Reviews.
January 2026
| 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 $3,002 |
22 $3,002 |
23 $3,002 |
24 $3,002 |
| 25 $3,002 |
26 $3,002 |
27 $3,002 |
28 $3,002 |
29 $3,002 |
30 $3,002 |
31 $3,002 |
February 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $3,002 |
02 $3,002 |
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 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 | 02 | 03 | 04 | 05 | 06 | 07 |
| 08 $2,501 |
09 $2,501 |
10 $2,501 |
11 $2,501 |
12 $2,501 |
13 $2,501 |
14 $2,501 |
| 15 $2,501 |
16 $2,501 |
17 $2,501 |
18 $2,501 |
19 $2,501 |
20 $2,501 |
21 $2,501 |
| 22 $2,501 |
23 $2,501 |
24 $2,501 |
25 $2,501 |
26 $2,501 |
27 $2,501 |
28 $2,501 |
| 29 $2,501 |
30 $2,501 |
31 $2,501 |
April 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $2,501 |
02 $2,501 |
03 $2,501 |
04 $2,501 |
|||
| 05 $2,501 |
06 $2,501 |
07 $2,501 |
08 $2,501 |
09 $2,501 |
10 $2,501 |
11 $2,501 |
| 12 $2,501 |
13 $2,501 |
14 $2,501 |
15 $2,501 |
16 $2,501 |
17 $2,501 |
18 $2,501 |
| 19 $2,501 |
20 $2,501 |
21 $2,501 |
22 $2,501 |
23 $2,501 |
24 $2,501 |
25 $2,501 |
| 26 $2,501 |
27 $2,501 |
28 $2,501 |
29 $2,501 |
30 $2,501 |
May 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $2,168 |
02 $2,168 |
|||||
| 03 $2,168 |
04 $2,168 |
05 $2,168 |
06 $2,168 |
07 $2,168 |
08 $2,168 |
09 $2,168 |
| 10 $2,168 |
11 $2,168 |
12 $2,168 |
13 $2,168 |
14 $2,168 |
15 $2,168 |
16 $2,168 |
| 17 $2,168 |
18 $2,168 |
19 $2,168 |
20 $2,168 |
21 $2,168 |
22 $2,168 |
23 $2,168 |
| 24 $2,168 |
25 $2,168 |
26 $2,168 |
27 $2,168 |
28 $2,168 |
29 $2,168 |
30 $2,168 |
| 31 $2,168 |
June 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $2,168 |
02 $2,168 |
03 $2,168 |
04 $2,168 |
05 $2,168 |
06 $2,168 |
|
| 07 $2,168 |
08 $2,168 |
09 $2,168 |
10 $2,168 |
11 $2,168 |
12 $2,168 |
13 $2,168 |
| 14 $2,168 |
15 $2,168 |
16 $3,169 |
17 $3,169 |
18 $3,169 |
19 $3,169 |
20 $3,169 |
| 21 $3,169 |
22 $3,169 |
23 $3,169 |
24 $3,169 |
25 $3,169 |
26 $3,169 |
27 $3,169 |
| 28 $3,169 |
29 $3,169 |
30 $3,169 |
July 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $3,169 |
02 $3,169 |
03 $3,169 |
04 $3,169 |
|||
| 05 $3,169 |
06 $3,169 |
07 $3,169 |
08 $3,169 |
09 $3,169 |
10 $3,169 |
11 $3,169 |
| 12 $3,169 |
13 $3,169 |
14 $3,169 |
15 $3,169 |
16 $3,169 |
17 $3,169 |
18 $3,169 |
| 19 $3,169 |
20 $3,169 |
21 $3,169 |
22 $3,169 |
23 $3,169 |
24 $3,169 |
25 $3,169 |
| 26 $3,169 |
27 $3,169 |
28 $3,169 |
29 $3,169 |
30 $3,169 |
31 $3,169 |
August 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $3,169 |
||||||
| 02 $3,169 |
03 $3,169 |
04 $3,169 |
05 $3,169 |
06 $3,169 |
07 $3,169 |
08 $3,169 |
| 09 $3,169 |
10 $3,169 |
11 $3,169 |
12 $3,169 |
13 $3,169 |
14 $3,169 |
15 $3,169 |
| 16 $3,169 |
17 $3,169 |
18 $3,169 |
19 $3,169 |
20 $3,169 |
21 $3,169 |
22 $3,169 |
| 23 $3,169 |
24 $3,169 |
25 $3,169 |
26 $3,169 |
27 $3,169 |
28 $3,169 |
29 $3,169 |
| 30 $3,169 |
31 $3,169 |
September 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $3,169 |
02 $2,501 |
03 $2,501 |
04 $2,501 |
05 $2,501 |
||
| 06 $2,501 |
07 $2,501 |
08 $2,501 |
09 $2,501 |
10 $2,501 |
11 $2,501 |
12 $2,501 |
| 13 $2,501 |
14 $2,501 |
15 $2,501 |
16 $2,501 |
17 $2,501 |
18 $2,501 |
19 $2,501 |
| 20 $2,501 |
21 $2,501 |
22 $2,501 |
23 $2,501 |
24 $2,501 |
25 $2,501 |
26 $2,501 |
| 27 $2,501 |
28 $2,501 |
29 $2,501 |
30 $2,501 |
October 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $2,501 |
02 $2,501 |
03 $2,501 |
||||
| 04 $2,501 |
05 $2,501 |
06 $2,501 |
07 $2,501 |
08 $2,501 |
09 $2,501 |
10 $2,501 |
| 11 $2,501 |
12 $2,501 |
13 $2,501 |
14 $2,501 |
15 $2,501 |
16 $2,501 |
17 $2,501 |
| 18 $2,501 |
19 $2,501 |
20 $2,501 |
21 $2,501 |
22 $2,501 |
23 $2,501 |
24 $2,501 |
| 25 $2,501 |
26 $2,501 |
27 $2,501 |
28 $2,501 |
29 $2,501 |
30 $2,501 |
31 $2,501 |
November 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $2,501 |
02 $2,501 |
03 $2,501 |
04 $2,500 |
05 $2,500 |
06 $2,500 |
07 $2,500 |
| 08 $2,500 |
09 $2,500 |
10 $2,500 |
11 $2,500 |
12 $2,500 |
13 $2,500 |
14 $2,500 |
| 15 $2,500 |
16 $2,500 |
17 $2,500 |
18 $2,500 |
19 $2,500 |
20 $2,500 |
21 $2,500 |
| 22 $2,500 |
23 $2,500 |
24 $2,500 |
25 $2,500 |
26 $2,500 |
27 $2,500 |
28 $2,500 |
| 29 $2,500 |
30 $2,500 |
December 2026
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
| 01 $4,100 |
02 $4,100 |
03 $4,100 |
04 $4,100 |
05 $4,100 |
||
| 06 $4,100 |
07 $4,100 |
08 $4,100 |
09 $4,100 |
10 $4,100 |
11 $4,100 |
12 $4,100 |
| 13 $4,100 |
14 $4,100 |
15 $4,100 |
16 $4,100 |
17 $4,100 |
18 $4,100 |
19 $4,100 |
| 20 $4,100 |
21 $4,100 |
22 $4,100 |
23 $4,100 |
24 $4,100 |
25 $4,100 |
26 $4,100 |
| 27 $4,100 |
28 $4,100 |
29 $4,100 |
30 $4,100 |
31 $4,100 |
Ages 18 or above
Ages 2-17
Under 2
Bringing your pets?
Please select dates
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