Luxury Vacation Rentals in Kahala, Oahu – Oceanfront Elegance Minutes from Waikiki
Kahala vacation rentals offer exclusive accommodations just outside Waikiki. Discover oceanfront estates and private luxury homes with pools, gardens, and stunning views in Oahu's most elite residential neighborhood-perfect for peaceful retreats near Honolulu's top attractions.
Why Stay in Kahala?
Kahala is known as Oahu's “Beverly Hills”-a coastal enclave of quiet streets, sprawling mansions, and pristine beachfront. Located just east of Waikiki, this tranquil neighborhood provides proximity to the city while feeling worlds away. It's a top choice for celebrities, business travelers, and families seeking privacy, comfort, and understated luxury.
Upscale Amenities and Refined Living
Our curated collection of Kahala vacation homes includes elegant beachfront properties with private pools, designer interiors, chef-grade kitchens, and oceanview lanais. Whether you're hosting a multigenerational getaway or a romantic retreat, Kahala provides space, security, and ambiance few other Oahu destinations can match.
Top Attractions Near Kahala
- Kahala Mall – Boutique shopping and casual dining
- Waialae Country Club – Prestigious golf course hosting the Sony Open
- Diamond Head Crater – Just minutes away for scenic hiking and views
- Kahala Beach – Secluded shoreline ideal for morning swims and sunbathing
Key Features of Kahala Vacation Rentals
- Private pools, lanais, and tropical gardens
- Ocean views or direct beachfront access
- High-end kitchens and expansive living areas
- Exclusive location close to Waikiki and Honolulu
- Ideal for weddings, extended family stays, and high-end escapes
If you're seeking sophisticated island living with a balance of serenity and access, Kahala offers one of the most refined vacation experiences in all of Hawaii. Explore our listings below and elevate your stay with a luxury retreat in this timeless neighborhood.
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 Kahala Seaside, a spacious...
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 and spacious studio with 1...
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, deciding whether to go to...
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. Please inquire about...
Pili Pono: Elegant Honolulu Retreat with 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 Pili Pono by GatherExperience the...
Spectacular home, pool spa near Kahala Beach. MAY CANCELLATION - CALL NOW!
An Oasis of Calm. Understated Elegance. These are the thoughts that first come to mind as you enter this stunning, contemporary property, offering a quintessential Hawaii experience in one of Oahu’s most upscale neighborhoods, steps away from the world-renowned,...
Kahala Oceanside – Coastal Sanctuary with Panoramic Views
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 endless attractions of...
Island Adventure: Minivan Rental, Contact Us
Mahalo is the Hawaiian word for thanks, and a feeling of profound gratitude is what inspired this beautiful home. From the moment you arrive at Hale Mahalo, you’ll understand why. This lovely 3-bedroom, 3-bathroom home is a tribute to the stunning beauty of its...
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 inside and be greeted by a...
Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach
Treat yourself to ultimate island luxury in this architecturally designed $5.5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite estate is a 5-MINUTE WALK...
Kahala Breeze: Modern Tropical Home with Pool & Private 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.Experience the laidback luxury and authentic...
Ho'okipa Villa: Historic Home + Guest Cottage in Kahala
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 Living Welcome to Ho'okipa...
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 coast. Also, in very short...
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 Kahala Cottage by Gather, your...
Island Adventure: Minivan Rental, Contact Us
Welcome to Hale Lilikoi, your private paradise on Oahu. Named for the vibrant and sweet lilikoi (passion fruit), this home embodies the passion and beauty of the islands. From the moment you step inside, you'll be captivated by sweeping, panoramic views of the Pacific...
Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath
Minimum rental period of 30 days, Rental included Electric, Water, Cable WiFi Clean the yard twice a month and clean the swimming pool every Tuesday and FridayUpscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the...
Kahala Beachfront Estate – Private Resort-Style Living
For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10 Night Minimum over the Christmas/New Years Holiday Season at $7,500 per night.Spacious beachfront estate is situated on lush tropical grounds, nestled in...
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 walk from Waikiki, discover your...
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 dream tropical vacation begin when...
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 lanai. Situated only 2 miles...
Island Adventure: Minivan Rental, Contact Us
In Hawaii, "Aloha" is more than a greeting; it's a way of life—a spirit of love, peace, and compassion. We designed Hale Aloha to be a true embodiment of that spirit. This beautiful 4-bedroom home welcomes you with warmth, comfort, and some of the most breathtaking...
Magnificent Waikiki Mountain Views! Free Parking, Wi-Fi, Pool & More!
Waikiki Sunset #2503 – 229 Paoakalani Ave.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, and free Wi-Fi—perfect for couples and small families!The...
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 Galore , Look at the Famous...
KAHALA BEACH APARTMENT
FORGET YOUR WORRIES IN THIS SPACIOUS AND SERENE SPACE. THIS MODERN RESIDENCE IS NEWLY RENOVATED AND EXTREMELY CLEAN. LOCATED ON THE BEAUTIFUL KAHALA BEACH. UNIT OFFERS PRIVATE OUTDOOR PATIO WITH SEATING AND DINING TABLE TO HELP YOU ENJOY THE TROPICAL BEAUTY OF THE...
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 on an idyllic cove beach,...
Kahala Beachfront Unique Bohemian Home
($99- Clean Fee special for Spring bookings, please inquiry. Car/ Suv Available at discounted rate- pls inquire)A relaxing escape in this abode situated in the coveted Kahala, tucked away for your enjoyment . ENTIRE High end condo-home for rent (2bedroom 2bath) with a...
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 equipped kitchen, which includes a...
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 apartments at Kahala Beach....
The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood
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, Privacy, and Grand-Scale Elegance at...
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 Kahala ZenNestled in the...
Large 2BD/2BA Kahala Beach Front Condo Furnished
A relaxing escape in Kahala high end condo. 2 Bedrooms with oversized master Bedroom and 2 Bathrooms. Full kitchen, dinning area, large living room with TV and high speed internet, amazing lanai with partial ocean view.HAWAIIN PARADIZE in Kahala! The ocean-front...
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 paradise at Kahala Beachfront Villa...
BEACHFRONT - 2bdrm 2 bath, fine art, contemporary design in luxury building.
Next to world-class Kahala Resort, 24 hr security on Kahala Beach. Condo offers 5G internet, central AC, one covered parking, washer/dryer, linens, full open kitchen, 3 flatscreen TVs, DVD, two bedrooms, two full baths. Access Kahala Resort spa, restaurants, activities,...
Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast
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 extraordinary beachfront location,...
Experience Honolulu, 3BR Home w/ Modern Comfort & Ocean Views
PERFECT FOR:Family | Group | Digital nomads | Pet lovers | View enthusiastsTHE SPACE:- 3BR w/ queen beds- Sleeps up to 6- Private deck w/ Diamond Head views- Full kitchen- In-unit washer & dryer- A/C all throughoutUNBEATABLE LOCATION:- 7 mins → Diamond Head Beach- 5-8...
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 starts at first glance with Kahala...
Diamond Head Grandeur: Kahala Luxury Villa with Ocean View
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 and tranquility in your very own...
Kahala Resort Style Home - Aug/Sept 2022
Fabulous Kahala home close to Waialae Country Club, Kahala Beaches, Shopping, and Dining. 5 minutes from Waikiki and downtown! Great home offers privacy that opens up to the huge lanai with pool, spa, and cabana. True indoor/outdoor Hawaiiana living. 2 car garage with...
Come & experience the calmness & serenity with the birds singing!
STUNNING new home with views of Diamond Head, the ocean and Waikiki. Super spacious of 1980 sq. ft., immaculate 3 bedrooms (1 King bed & 2 queen beds) and 2 full bathrooms, open floor plan, huge and well-equipped kitchen with cookware, utensils & more, top of line...
Relaxing tropical retreat near Diamond Head. Unwind and rejuvenate your senses.
Experience a calming Oasis at the Kahala Beach Apartments. This peaceful retreat is a fully furnished 2 bedroom, 2 bath dwelling located on the 1st floor and has 1 parking stall included. Cool off comfortably with fully integrated air conditioning throughout the space...
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 CROWN JEWEL – A MODERN DIAMOND HEAD HOME –...
15% Off Summer Special! Luxury Oceanfront Estate: Banyan House 4BD
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.Banyan House is Oahu’s most luxurious...
Pet Friendly Guesthouse + Parking
LOCATIONThis 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 Juice, Honolulu Zoo,...
Long term rental near beach in Kahala with Pool
Beautiful house located two blocks from the beach with pool.Five bedrooms, Five baths, fully furnished with internet, cable and utilities included.30 day minimum rental, no exceptions.$46,800/month
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 Juice, Honolulu Zoo, Close to...
Serenity in the Sky!
Gorgeous brand new home with 3 bedrooms and 3 full bathrooms with beautiful views, privacy and absolute serenity. All new stainless appliances & new furniture, beautiful kitchen with granite and spectacular view and WIFI.!Wake up and enjoy the best sunrise on the island...
Home in the Sky!
Stunning brand new home with 3 bedrooms and 3 full bathrooms with beautiful views and absolute serenity. All new stainless appliances & new furniture, beautiful kitchen with granite and spectacular view and WIFI.!Wake up to the best sunrise on the island and enjoy the...
Kahala Oasis: 6BR Retreat with 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 Kahala Oasis by Gather, an...
Ultra Luxury Oceanfront 8 BD 8.5 BA Pool & Hot Tub in Diamond Head
Honeyed Jade is an enchanting Diamond Head vacation rental estate located on the exquisite island of Oahu. Oahu is an ideal island to visit if you envision yourself amid beautiful Pacific blue waters and within easy access to shopping and first-class restaurants....
Pet Friendly Private Room In Shared Guesthouse
Private Room Rental in Shared GuestHouseVery Walkable Location. We're Located Within Walking Distance To Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking Trail, Safeway Grocery Store, Restaurants, Starbucks, Jamba Juice, Honolulu Zoo, Close to...