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...
Crutchfield Estate - Charming Historical Home in Honolulu
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 refrigerator and dishwasher. Morning...
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...
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...
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 plate lunch, Leonard’s...
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- 12 Night Minimum over the Christmas/New Years Holiday Season at $8,400 per night.Spacious beachfront estate is situated on lush tropical grounds,...
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...
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...
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 many attractions nearby....
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...
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,...
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...
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...
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,...
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...
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 –...
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...
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...
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...
Kahala Lani: Balinese-Inspired Home with 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 multi-generational families and golf...