Kahala Vacation Rentals

Kahala vacation rentals offer an upscale retreat on Oahu’s south shore, where luxury living meets island elegance. Just minutes from Waikiki, this serene neighborhood is known for its oceanfront estates, quiet beaches, and prestigious feel-making it one of Honolulu’s most sought-after destinations.

Choose from expansive beachfront homes, stylish villas, or modern condos tucked into lush tropical landscapes. Many Kahala rentals feature private pools, gourmet kitchens, lanais with ocean views, and direct beach access, creating the ultimate setting for a relaxing getaway or a memorable family vacation.

Stroll to Kahala Beach for a peaceful swim, visit nearby Diamond Head for a scenic hike, or enjoy fine dining and shopping at Kahala Mall. For those seeking tranquility without sacrificing convenience, Kahala blends exclusivity with easy access to Honolulu’s attractions.

Whether you’re planning a romantic escape, multi-generational trip, or long-term stay, Kahala vacation rentals deliver comfort, privacy, and the refined beauty of island living-perfect for travelers who want to unwind in style.

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 $401 
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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 $1,204 
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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

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to
Registration Number: TA-038-170-4192-01, GE-038-170-4192-01, 350150260000

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $429 
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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

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Kahala Luxury
Registration Number: TA-088-184-4224-01, 350100100000, GE-088-184-4224-01

  • 5 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Honolulu
from $1,004 
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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

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Experience
Registration Number: 350030310000, TA-065-534-9760-01, GE-065-534-9760-01

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $631 
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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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Honolulu Condo for Rent Steps to Kahala Beach

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!

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to
Registration Number: 350040510000, TA-188-470-4768-01, GE-188-470-4768-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 7
Hawaii> Honolulu
from $703 
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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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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 $158 
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Hale Mahie by Gather: Spanish Colonial Historic Home w/ Ocean Views & AC

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

A 10-minute
Registration Number: TA-044-602-3680-01, 310330200000, GE-044-602-3680-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $819 
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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

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Let your
Registration Number: TA-021-803-2128-01, GE-021-803-2128-01, 1350020240000

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $986 
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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 $316 
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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 $334 
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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

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Admiration
Registration Number: TA-139-412-1216-01, GE-139-412-1216-01, 350130320000

  • 5 bedroom
  • 5 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $1,586 
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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

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Boasting an
Registration Number: TA-104-487-9872-01, 350060190000, GE-104-487-9872-01

  • 7 bedroom
  • 8 bathroom
  • Sleeps 14
Hawaii> Honolulu
from $3,520 
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Kahala Lani: Balinese-inspired Home immersed in nature, Private Pool

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Ideal for
Registration Number: TA-048-116-5312-01, GE-048-116-5312-01, 350080310000

  • 5 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Honolulu
from $2,069 
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Diamond Head Grandeur by Gather: Luxury Villa w/ Ocean View & Private Pool

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Find peace
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

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Luxury,
Registration Number: GE-132-155-2896-01, TA-132-155-2896-01, 350040280000

  • 5 bedroom
  • 6 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $7,369 
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Kahala Beachside Villa: Lux Condo w/ Pool, Balcony Views & Beach Access

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Escape to
Registration Number: 1350230020117, GE-004-895-1296-02, TA-004-895-1296-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $360 
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Luxury Kahala Oasis by Gather: Spacious 6BR Retreat w/ Pool, Spa & Near Beach

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to
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

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to
Registration Number: 350040310000, GE-183-524-3008-01, TA-183-524-3008-01

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $991 
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Pili Pono by Gather: Elegant Honolulu Retreat w/ Pool & Private Oasis

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to
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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