Kahala Vacation Rentals

Kahala is an upscale Honolulu neighborhood that offers the best of both worlds - pristine white-sand beaches combined with the comfort of luxurious vacation rentals and all the amenities they come with. Choosing Kahala for your vacation destination comes with lots of benefits - you will be away from the hustle and bustle of Waikiki and in the same time be just a 10-minute drive away from it and its endless entertainment choices. Kahala is also within easy reach of a variety of beaches, as well as a world-class golf course. Browse through this fine selection of Kahala vacation homes below and find your perfect home away from home.

Island Adventure: Minivan Rental, Contact Us

UNPARALLELED VIEWS!
Endless hypnotizing panoramic views await you from this well maintained 3 bedroom, 3 bathroom cottage style house nestled in the highly coveted hills adjacent to Waikiki Beach.
Our home offers over 2,000 sq ft of ...
Registration Number: GE-123-456-7890-01, TA-123-456-7890-01, 1234567890000

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $434 
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Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath

Upscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the nearest beach, Kahala Hotel, Waialae Country club. 6-minute drive to the world famous Waikiki Beach, Diamond Head hiking, Rainbow's ...
Registration Number: 230360390448, TA-008-444-7232-01, GE-008-444-7232-01

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $521 
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Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise

Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, ...
Registration Number: GE-107-728-0768-01, TA-107-728-0768-01, 330310160000

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $305 
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Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops

Prices start at $5,250/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Welcome to Kahala Cottage by Gather, your home-away-from-home in the heart of Oahu’s exclusive Kahala ...
Registration Number: TA-038-170-4192-01, GE-038-170-4192-01, 350150260000

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $376 
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Beachfront, Kahala Mini Resort, w/2 pools, private tennis court, gated, A/C,

For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10- 12 Night Minimum over the Christmas/New Years Holiday Season at $8,400 per night.

Spacious beachfront estate is ...
Registration Number: GE-005-323-3664-01, TA-005-323-3664-01, 90/TVU-0376, 350060160000

  • 7 bedroom
  • 7 bathroom
  • Sleeps 14
Hawaii> Honolulu
from $6,745 
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Kahala Oceanside- 6 Bed/6 1/2 bath/Sleeps 14

Kahala Oceanside is a private paradise retreat that comfortably sleeps 14. This luxurious ocean front hideaway on the South Shore of Oahu, known for its spectacular sunsets, is just minutes away from fine eateries, world-famous hikes, and the ...
Registration Number: 1350030350000, GE-053-250-7136-01, TA-053-250-7136-01

  • 6 bedroom
  • 7 bathroom
  • Sleeps 15
Hawaii> Honolulu
from $4,190 
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Charming Historical Home - Crutchfield Estate

This spectacular French Tudor exudes a casual elegance and the comfort of the islands. Inside you will find gleaming wood floors, an elegant fireplace, crown molding and spacious bright rooms. The kitchen is fully equipped with a new ...
Registration Number: TA-112-501-9648-01, GE-112-501-9648-01

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $1,602 
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Ho'okipa Villa: Historic Home+Guest Cottage in Kahala near the Beach w/Pool & AC

Prices start at $12,000/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote

Kahala Luxury Living

Welcome to Ho'okipa Villa! Built in 1938 and recently renovated, this luxury home ...
Registration Number: TA-088-184-4224-01, 350100100000, GE-088-184-4224-01

  • 5 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Honolulu
from $560 
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Comfort and Elegance with stunning views of Diamond Head

Newly renovated 3 bedroom, 2.5 bath home on Maunalani Hts. Tastefully furnished with high quality bedroom, living room and dining room furniture. HD Smart T.V.s in living room, kitchen and bedroom. Fully functional kitchen with new dishes, ...
Registration Number: TA-187-879-4240-02, 330180700000, GE-186-879-4240-01

  • 0 bedroom
  • 0 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $267 
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Kahala Breeze: Modern Tropical Home w/Pool, Private Yard, & A/C. Kahala Breeze

Prices start at $14,010/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Experience the laidback luxury and authentic island living of Kahala Breeze, a spacious four-bedroom home that ...
Registration Number: 350030310000, TA-065-534-9760-01, GE-065-534-9760-01

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $626 
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Cottage with Private Salt Water Pool

30 night minimum
This beautiful recently updated cottage is nestled in the quiet, safe, and upscale neighborhood of Kahala. Excellent location! Just minutes to Waikiki, nearby parks and the pretty white-sand beaches of the East Honolulu ...
Registration Number: TA-108-852-8384-01, GE-108-852-8384-01, 13526023

  • 1 bedroom
  • 1 bathroom
  • Sleeps 5
Hawaii> Honolulu
from $218 
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Steps to Kahala Beach, quiet, King bed, patio, parking, A/C, kitchenette & BBQ

Ask owner about available dates/rates. The perfect studio for a couple on their Hawaiian get-away who want to live like locals during their stay. Please inquire about your specific dates and we can try to accommodate your stay. This beautiful ...
Registration Number: TA-094-014-7712-01, GE-151-279-8208-01, 1350300320000

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Honolulu
from $284 
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Kahala Seaside: Beautiful Nautical-Themed Home w/AC, Yard, Private Pool & Spa!

Prices start at $13,500/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Welcome to Kahala Seaside, a spacious two-story garden view home featuring four bedrooms, three-and-a-half ...
Registration Number: 350040510000, TA-188-470-4768-01, GE-188-470-4768-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 7
Hawaii> Honolulu
from $740 
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Close to Kahala Beach/Air Conditioning/Heated Pool/Clean/Quiet Neighborhood

Ask owner about available dates/rates. Elegantly remodeled in 2018, this one level, very clean, 4 bedroom & 3 bath home, has 2 master suites, a gourmet kitchen, air conditioning in every bedroom & high end finishes throughout this private oasis....
Registration Number: GE-094-014-7712-01, TA-094-014-7712-01, 1350300320000

  • 5 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $2,241 
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Fabulous, Renovated Large 3BR Condo on Kahala Beach

Welcome to our newly renovated slice of paradise at Kahala Beach! Nestled in one of the most sought-after neighborhoods in Honolulu, this spacious 3-bedroom, 2-bathroom property promises a luxurious escape for your Hawaiian getaway.

Step ...
Registration Number: TA-052-736-1536-01, GE-052-736-1536-01, 1350230020025

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $381 
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Beatiful Kahala Estate Across The Street from Kahala Beach

Steps from beautiful Kahala Beach, you will find your Estate. As soon as you open the front gate, you will be welcomed with lush tropical landscape.

The property is located in the coveted Kahala neighborhood, a five minute walk to the ...
Registration Number: GE-046-812-9792-01, TA-046-812-9792-01, 350070020000

  • 3 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $1,230 
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A Quiet Honolulu LUX STUDIO near Diamond Head & Waikiki w/ private yard space

Welcome to the Bird of Paradise, similar to a boutique hotel experience in the Diamond Head/Kahala neighborhood. This Honolulu vacation rental is a short drive from Waikiki, International Marketplace, Ala Moana Shopping Center, Waikiki ZOO, and ...
Registration Number: TA-188-577-3824-01, GE-188-577-3824-01, 350140350000

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Honolulu
from $160 
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Hale Mahie by Gather: Spanish Colonial Historic Home w/ Ocean Views & AC

A 10-minute walk from Waikiki, discover your own private paradise nestled at the base of Diamond Head in Honolulu’s renowned Gold Coast. Built in 1926 and beautifully remodeled with modern luxuries, Hale Mahie is notable as an example of the ...
Registration Number: TA-044-602-3680-01, 310330200000, GE-044-602-3680-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $755 
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BIG ALOHA & AWESOME VIEW AT THIS HAWAIIAN HOME!

~Breezy Spacious and Welcoming Vacation Home~
This Hawaiian home sits up on the mountain with unbelievable, panoramic views of the Pacific Ocean, Diamond Head, Waikiki, and downtown. Watch sunsets, fireworks, whales, and rainbows from the ...
Registration Number: GE-122-615-2448-01, TA-122-615-2448-01, 330310320000

  • 4 bedroom
  • 3 bathroom
  • Sleeps 7
Hawaii> Honolulu
from $258 
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Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi

Let your dream tropical vacation begin when you step into the olden days of Hawai’i here at Hale Le’ahi, an illustrious and expansive 3 story plantation board and baton wood-framed estate located on the lower slopes of the world famous ...
Registration Number: TA-021-803-2128-01, GE-021-803-2128-01, 1350020240000

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $970 
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Kahala Valley 2Bed Cottage, Sleeps 6, Quiet backyard w/ peekaboo views

This 2 bedroom sleeps up to 6 in the valley above Diamond Head known as Kahala. Its the perfect balance of close to Waikiki and the highway but away from the hustle and bustle of things. Less than a $15 Uber/Lyft ride to Waikiki if you want to ...
Registration Number: TA-157-641-9328-01, GE-157-641-9328-01, 1350550410000

  • 3 bedroom
  • 1 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $289 
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Magnificent Waikiki Mountain Views! Free Parking, Wi-Fi, Pool & More!

Waikiki Sunset #2503 – 229 Paoakalani Ave.

NEW TO OUR INVENTORY! Enjoy the lush greenery of the Ko'olau Mountains and exquisite Hawaiian trade winds from your private lanai! This cozy rental features central A/C, a full kitchen, free ...
Registration Number: 260280110249, GE-159-961-1904-01, TA-159-961-1904-01

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Honolulu
from $300 
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Spacious Family Home With Gorgeous Sunset Views of Diamond Head

This is a truly a local style experience property and the area of Kahala is full of the best of the best of locations on the Island of Oahu with everything close by: City Life , Awesome Beaches , Great Dinning , Tropical Hiking Trails & Views ...
Registration Number: TA-105-889-1776-01, GE-105-889-1776-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 7
Hawaii> Honolulu
from $517 
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Right on the beach near Diamond Head and 4 miles from Waikiki!

On the beach, in a coveted luxury resort location are the Kahala Beach condos, adjacent to the Kahala Hotel, the only 5-star Hawaiian destination. Secure, with 24/7 guards, keyed building access, and a private underground parking garage. Sited ...
Registration Number: GE-165-278-3616-01, TA-165-278-3616-01, 1350230020146

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Honolulu
from $219 
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Breezy Ocean View Waikiki Condo with Free Parking!

The pool and all associated amenities will be closed starting April 7, 2025, for an estimated duration of 10 to 14 months to accommodate the Recreation Deck renovation project.

Waikiki Banyan Ocean View Corner Condo comes with a fully ...
Registration Number: 260250050092, TA-121-578-0864-01, GE-121-578-0864-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Honolulu
from $321 
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Kahala Beach #446 Vacation Rental

This highly desirable top-floor unit overlooks the lovely koi pond and provides the best views of the sky and stars. The lanai is oriented to the afternoon sun and sunset. Importantly, its top floor position makes it one of the most quiet ...
Registration Number: GE-003-036-7744-01, TA-003-036-7744-01, 1350230020145

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Honolulu
from $326 
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One of a Kind Luxury

FEATURED IN ARCHITECTURAL DIGEST MAGAZINE!

Are you ready to graduate from the Presidential Suite? Are you looking for the most relaxing vacation accommodation?

*Specials not available during Peak Season*

This OCEANFRONT ...
Registration Number: GE-092-683-8784-01, TA-180-161-9456-01, 31040027

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $4,758 
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Luxurious Kahala Grand Splendor: Private Home w/Pool, Spa, AC & Lush Landscaping

Prices start at $24,510/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Admiration starts at first glance with Kahala Grand Splendor by Gather, located in a luxury residential area in ...
Registration Number: TA-139-412-1216-01, GE-139-412-1216-01, 350130320000

  • 5 bedroom
  • 5 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $1,925 
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Pet Friendly Guesthouse + Parking

LOCATION
This is location is absolutely amazing! It's very walkable and safe in the morning, and evening. Walk to Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking trail, Safeway grocery store, restaurants, Starbucks, Jamba...
Registration Number: no, TA-124-162-4576-01, GE-124-162-4576-01, 31012073

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Honolulu
from $126 
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Kahala Beachside Estate: Luxury Estate w/Pool, Jacuzzi, AC & Spacious Yard

Boasting an extraordinary beachfront location, this private Kahala vacation rental estate provides all the modern luxury features your large group requires, with the charm of old Hawaii. Kahala Beachside Estate offers direct beach access, its ...
Registration Number: TA-104-487-9872-01, 350060190000, GE-104-487-9872-01

  • 7 bedroom
  • 8 bathroom
  • Sleeps 14
Hawaii> Honolulu
from $4,213 
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Kahala Lani: Balinese-inspired Home immersed in nature, Private Pool

Prices start at $22,500/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Ideal for multi-generational families and golf enthusiasts, this exquisite five bedroom, four bath home blends both...
Registration Number: TA-048-116-5312-01, GE-048-116-5312-01, 350080310000

  • 5 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Honolulu
from $2,036 
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Diamond Head Grandeur by Gather: Luxury Villa w/ Ocean View & Private Pool

Find peace and tranquility in your very own 5-bedroom, 5.5-bathroom villa here at Diamond Head Grandeur in the centralized neighborhood of Kahala on Oahu. Around the corner from the Diamond Head State Monument, this stunning property is just 15 ...
Registration Number: 310400040001, TA-076-121-8560-01, GE-076-121-8560-01

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $2,163 
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The Kahala Mansion: Luxury Home w/ Pool, Golf Stimulator, AC & Beach Access

Luxury, Privacy, and Grand-Scale Elegance at Honolulu’s Most Exclusive Estate
Discover The Kahala Mansion, a luxury estate on prestigious Kahala Avenue steps away from the beach. Perfect for serene retreats or grand events, this property ...
Registration Number: GE-132-155-2896-01, TA-132-155-2896-01, 350040280000

  • 5 bedroom
  • 6 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $6,572 
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Kahala Beachside Villa: Lux Condo w/ Pool, Balcony Views & Beach Access

Escape to paradise at Kahala Beachfront Villa by Gather, a luxurious two-bedroom, two-bathroom condo perfect for up to six guests. Nestled in the prestigious Kahala Beach area in Honolulu, HI, this vacation rental offers the best of beach living...
Registration Number: 1350230020117, GE-004-895-1296-02, TA-004-895-1296-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $350 
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Luxury Kahala Oasis by Gather: Spacious 6BR Retreat w/ Pool, Spa & Near Beach

Welcome to Kahala Oasis by Gather, an expansive 6-bedroom, six-and-a-half-bathroom luxury retreat nestled along the prestigious Kahala Avenue in Honolulu, Hawaii. This spacious estate comfortably accommodates up to fourteen guests and offers the...
Registration Number: 1350070050000, TA-153-997-3120-01, GE-153-997-3120-01

  • 6 bedroom
  • 7 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $769 
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Kahala Zen by Gather: Spacious 5BR Modern Oasis w/ Studio & Lush Garden

Welcome to Kahala Zen

Nestled in the prestigious Kahala neighborhood of Honolulu, Hawaii, Kahala Zen is a historic 5-bedroom, 4-bathroom retreat blending timeless charm with modern amenities. With a thoughtfully designed layout, including...
Registration Number: 350040310000, GE-183-524-3008-01, TA-183-524-3008-01

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $855 
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Pili Pono by Gather: Elegant Honolulu Retreat w/ Pool & Private Oasis

Welcome to Pili Pono by Gather

Experience the epitome of luxury and tranquility at Pili Pono, a stunning 5-bedroom, 6.5-bathroom estate in Honolulu’s prestigious Black Point neighborhood. Spanning over 7,470 square feet on a fully ...
Registration Number: 350020170000, TA-167-134-8224-02, GE-167-134-8224-01

  • 5 bedroom
  • 7 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $1,953 
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Pet Friendly Private Room In Shared Guesthouse

Private Room Rental in Shared GuestHouse

Very Walkable Location. We're Located Within Walking Distance To Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking Trail, Safeway Grocery Store, Restaurants, Starbucks, Jamba ...
Registration Number: no, TA-124-162-4576-01, GE-124-162-4576-01, 31012073

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Honolulu
from $98 
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Pet Friendly Private Room In Shared Guesthouse

Private Room Rental in Shared GuestHouse

Very Walkable Location. We're Located Within Walking Distance To Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking Trail, Safeway Grocery Store, Restaurants, Starbucks, Jamba ...
Registration Number: no, TA-124-162-4576-01, GE-124-162-4576-01, 31012073

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Honolulu
from $94 
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