Luxury Vacation Rentals in Kahala, Oahu

Kahala is one of Oahu’s most prestigious neighborhoods, offering a refined and peaceful retreat just minutes from the energy of Waikiki Beach and downtown Honolulu. Known for its spacious oceanfront estates, quiet streets, and manicured surroundings, Kahala appeals to travelers who want the convenience of the city without sacrificing privacy and serenity. This residential enclave blends exclusivity with tropical charm, making it a favorite for celebrities, executives, and discerning visitors.

Our selection of Kahala vacation rentals includes elegant homes with expansive floor plans, private pools, and lush gardens-perfect for families, couples, or extended stays. Many properties are steps from quiet beaches and just a short drive to top dining, luxury shopping, and cultural attractions. Here, you can relax in an upscale setting while remaining close to everything Honolulu has to offer.

If you’re seeking refined island living with easy access to the city and none of the noise, Kahala delivers an exceptional balance of comfort, convenience, and tranquility. Explore our listings to find your perfect luxury retreat in this exclusive corner of Oahu.

Sort By

Default View Price: Low to High Price: High to Low Bedrooms: Least to Most Bedrooms: Most to Least

• Select Default View Price: Low to High Price: High to Low Bedrooms: Least to Most Bedrooms: Most to Least

List

Map

Luxury Kahala Seaside 2-Story Garden View Home

Welcome to Kahala Seaside, a beautifully designed two-story home offering stunning garden views and luxurious amenities. This spacious property features four bedrooms and three-and-a-half bathrooms, comfortably accommodating up to eight guests.
Registration Number: 350040510000, TA-188-470-4768-01, GE-188-470-4768-01

• 4 bedroom
• 3 bathroom
• Sleeps 7

Hawaii> Honolulu

from $741 

View Property   Book Direct

Honolulu Condo for Rent Steps to Kahala Beach

Experience the perfect Hawaiian escape in this beautifully maintained and spacious studio designed for couples. The property offers a private, gated entrance and is completely separate from the owners' home, ensuring privacy and tranquility during your stay.

Registration Number: TA-094-014-7712-01, GE-151-279-8208-01, 1350300320000

• 1 bedroom
• 1 bathroom
• Sleeps 2

Hawaii> Honolulu

from $284 

View Property   Book Direct

Hawaii Vacation Home with Stunning Ocean Views

Experience the charm of this historic Hawaiian vacation home offering unobstructed views of the ocean, Diamondhead, and Waikiki from a spacious, beautifully updated house. The property features a large lanai perfect for sipping Kona coffee while soaking in the morning scenery or enjoying sunset dinners.
Registration Number: GE-107-728-0768-01, TA-107-728-0768-01, 330310160000

• 3 bedroom
• 1 bathroom
• Sleeps 6

Hawaii> Honolulu

from $305 

View Property   Book Direct

Luxury Hawaii Vacation Rental with Infinity Pool and Ocean Views

Feel the blend of casual elegance and island comfort in this spectacular French Tudor located in Honolulu's historic Maunalani Heights. Inside, gleaming wood floors, crown molding, and spacious, bright rooms create a welcoming atmosphere. The fully equipped kitchen features a new refrigerator and dishwasher, perfect for preparing meals.
Registration Number: TA-112-501-9648-01, GE-112-501-9648-01

• 4 bedroom
• 2 bathroom
• Sleeps 8

Hawaii> Honolulu

from $1,602 

View Property   Book Direct

Elegant 4BR Kahala Beach Home with Heated Pool

Step into this elegantly remodeled 4-bedroom, 3-bath home on a quiet street near Kahala Beach, perfect for a luxurious Hawaiian getaway. The property features two master suites and a private studio with a separate entrance, ideal for additional privacy or a second master bedroom.
Registration Number: GE-094-014-7712-01, TA-094-014-7712-01, 1350300320000

• 4 bedroom
• 3 bathroom
• Sleeps 8

Hawaii> Honolulu

from $2,241 

View Property   Book Direct

Renovated 3BR Home with Ocean Views on Maunalani Hts

5-bath home nestled on the scenic Maunalani Heights. The house combines modern comfort with stylish decor, featuring high-quality furniture in the bedrooms, living room, and dining area. Each room is equipped with HD Smart TVs, allowing you to unwind with your favorite shows after a day exploring the island.
Registration Number: TA-187-879-4240-02, 330180700000, GE-186-879-4240-01

• 0 bedroom
• 0 bathroom
• Sleeps 6

Hawaii> Honolulu

from $267 

View Property   Book Direct

Kahala Oceanside – Coastal Sanctuary with Panoramic Views

Kahala Oceanside is a luxurious private retreat on Oahu's South Shore, comfortably accommodating up to 14 guests. This stunning oceanfront estate offers breathtaking sunsets, modern amenities, and a prime location near top attractions. 5-bath layout that blends Hawaiian tradition with contemporary comfort.

Registration Number: 1350030350000, GE-053-250-7136-01, TA-053-250-7136-01

• 6 bedroom
• 6 bathroom
• Sleeps 15

Hawaii> Honolulu

from $4,190 

View Property   Book Direct

Hawaii Oahu Vista Cottage with Stunning Views

Immerse yourself in unparalleled panoramic views from this beautifully maintained 3-bedroom, 3-bathroom cottage nestled in the coveted hills near Waikiki Beach. With over 2,000 sq ft of versatile living space, this home offers the perfect setting for your Hawaiian getaway, whether you're relaxing in the hot tub on the private balcony, enjoying city and ocean vistas from the dining area, or hosting friends in the fully stocked kitchen.
Registration Number: GE-123-456-7890-01, TA-123-456-7890-01, 1234567890000

• 3 bedroom
• 3 bathroom
• Sleeps 8

Hawaii> Honolulu

from $383 

View Property   Book Direct

Luxury Renovated Home Near Kahala Beach

Welcome to our beautifully renovated retreat at Kahala Beach, located in one of Honolulu's most desirable neighborhoods. This spacious 3-bedroom, 2-bath home offers a perfect blend of comfort and luxury for your Hawaiian vacation. Inside, you'll find a contemporary interior decorated with modern furnishings and thoughtful touches throughout, creating a welcoming atmosphere.
Registration Number: TA-052-736-1536-01, GE-052-736-1536-01, 1350230020025

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Honolulu

from $381 

View Property   Book Direct

Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach

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 TO A SECLUDED WHITE SAND BEACH with excellent surfing.
Registration Number: 350020180000, GE-047-203-9424-01, TA-047-203-9424-01

• 4 bedroom
• 4 bathroom
• Sleeps 9

Hawaii> Honolulu

from $718 

View Property   Book Direct

Luxury 4-Bedroom Home in Kahala, Oahu

Experience the relaxed luxury and authentic island lifestyle at Kahala Breeze, a spacious four-bedroom home nestled in the lush surroundings of Oahu. This elegant residence combines natural beauty with modern comfort, making it an ideal retreat for families or groups seeking a memorable Hawaiian getaway.

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

• 4 bedroom
• 4 bathroom
• Sleeps 8

Hawaii> Honolulu

from $897 

View Property   Book Direct

Ho'okipa Villa: Luxury Kahala Beach Home

Welcome to Ho'okipa Villa, a stunning blend of vintage charm and modern luxury nestled in the coveted Kahala area. Built in 1938 and recently renovated, this spacious property offers four bedrooms and three bathrooms in the main house, including a luxurious Master Bedroom with an ensuite bath.
Registration Number: TA-088-184-4224-01, 350100100000, GE-088-184-4224-01

• 5 bedroom
• 4 bathroom
• Sleeps 14

Hawaii> Honolulu

from $955 

View Property   Book Direct

Charming Kahala Cottage with Private Salt Water Pool

Discover this beautifully updated cottage nestled in the peaceful and upscale Kahala neighborhood, offering a serene retreat just minutes from Waikiki and the East Honolulu coast's stunning beaches. With a minimum stay of 30 nights, this property is ideal for couples or families seeking a relaxing Hawaiian getaway.
Registration Number: TA-108-852-8384-01, GE-108-852-8384-01, 13526023

• 1 bedroom
• 1 bathroom
• Sleeps 5

Hawaii> Honolulu

from $218 

View Property   Book Direct

Kahala Cottage by Gather: Charming Oahu Retreat

Kahala Cottage by Gather offers a delightful island retreat in Oahu's prestigious Kahala neighborhood. This spacious two-bedroom, two-bath home comfortably accommodates up to eight guests, making it ideal for families or small groups seeking a relaxing Hawaiian escape.
Registration Number: TA-038-170-4192-01, GE-038-170-4192-01, 350150260000

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Honolulu

from $386 

View Property   Book Direct

Luxury Kahala Home Near Beaches and Shopping

Experience the charm of this upscale Kahala neighborhood, just a short walk to Kahala Mall, featuring Starbucks, Whole Foods, and various shops and restaurants. The home offers a relaxing lanai overlooking the pool, perfect for unwinding after a day of exploring.
Registration Number: 230360390448, TA-008-444-7232-01, GE-008-444-7232-01

• 5 bedroom
• 4 bathroom
• Sleeps 10

Hawaii> Honolulu

from $556 

View Property   Book Direct

Kahala Beachfront Estate – Private Resort-Style Living

Experience the ultimate tropical escape at this luxurious beachfront estate nestled among palm trees on Oahu. The property features expansive lush grounds, two sparkling swimming pools, a relaxing Jacuzzi, waterfalls, and your own private tennis court, providing ample space for relaxation and recreation.

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 

View Property   Book Direct

Luxury Diamond Head Vacation Cottage near Waikiki

This stunning property, available for monthly rental, combines historic charm with modern luxury. Located just a 10-minute walk from Waikiki and nestled at the foot of Diamond Head, Hale Mahie offers an exclusive Hawaiian retreat. Built in 1926 and meticulously remodeled, this home showcases the Spanish Colonial Revival style, a popular design in Hawaii during the early 20th century, and was designed by renowned architect Carl William Winstedt.
Registration Number: TA-044-602-3680-01, 310330200000, GE-044-602-3680-01

• 4 bedroom
• 3 bathroom
• Sleeps 8

Hawaii> Honolulu

from $790 

View Property   Book Direct

Spacious Hawaiian Vacation Home with Panoramic Views

Experience the perfect Hawaiian getaway in this spacious and welcoming mountain-top home offering breathtaking panoramic views of the Pacific Ocean, Diamond Head, Waikiki, and downtown Honolulu. The home features a vintage Hawaiian charm with three bedrooms, two bathrooms—one with a tub/shower and one with a shower—and a large living and dining area that comfortably seats eight.
Registration Number: GE-122-615-2448-01, TA-122-615-2448-01, 330310320000

• 3 bedroom
• 2 bathroom
• Sleeps 7

Hawaii> Honolulu

from $258 

View Property   Book Direct

Bird of Paradise Cozy Boutique Stay in Honolulu

Welcome to Bird of Paradise, a charming boutique-style vacation rental nestled in Honolulu's prestigious Kahala neighborhood. This cozy sanctuary offers a perfect blend of comfort, privacy, and convenience, making it an ideal retreat for travelers seeking an authentic Hawaiian experience.

Registration Number: TA-188-577-3824-01, GE-188-577-3824-01, 350140350000

• 1 bedroom
• 1 bathroom
• Sleeps 2

Hawaii> Honolulu

from $167 

View Property   Book Direct

Charming 2-Bedroom Cottage Near Waikiki with Ocean Views

This charming 2-bedroom cottage is nestled in the hillside above Diamond Head in the tranquil Kahala neighborhood, offering the perfect blend of privacy and convenience. Its location provides easy access to Waikiki, just a short $15 Uber or Lyft ride away, making it ideal for those wanting to enjoy the lively nightlife and dining options without sacrificing peace and quiet.

Registration Number: TA-157-641-9328-01, GE-157-641-9328-01, 1350550410000

• 3 bedroom
• 1 bathroom
• Sleeps 6

Hawaii> Honolulu

from $289 

View Property   Book Direct

Waikiki Sunset #2503 - Cozy Hawaii Condo Near Beach

Experience the best of Waikiki at Waikiki Sunset #2503, a charming condo ideally located just a 4-minute stroll from Waikiki Beach. Surrounded by lush greenery and offering stunning views of the Ko'olau Mountains, this cozy retreat is perfect for couples and small families seeking comfort and convenience.

Registration Number: 260280110249, GE-159-961-1904-01, TA-159-961-1904-01

• 1 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Honolulu

from $269 

View Property   Book Direct

Charming Kahala Hawaiian Home Near Diamond Head

This charming Hawaiian-style home in the prestigious Kahala area offers an authentic local experience with breathtaking views of the Diamond Head crater from nearly every room. Nestled in a quiet, private setting, the property provides a peaceful retreat while remaining close to the best attractions on Oahu.
Registration Number: TA-105-889-1776-01, GE-105-889-1776-01

• 4 bedroom
• 2 bathroom
• Sleeps 7

Hawaii> Honolulu

from $517 

View Property   Book Direct

Luxury Kahala Beach Condo with Ocean Views

Discover the exquisite Kahala Beach condos, nestled in a prestigious resort setting next to the iconic Kahala Hotel, Hawaii's only 5-star destination. This secure, top-floor unit offers unparalleled privacy with 24/7 security, keyed access, and a private underground parking garage.
Registration Number: GE-165-278-3616-01, TA-165-278-3616-01, 1350230020146

• 1 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Honolulu

from $219 

View Property   Book Direct

Waikiki Banyan Ocean View Corner Condo with Free Parking

The Waikiki Banyan Ocean View Corner Condo offers a perfect Hawaiian escape with stunning ocean views from the bedroom window. Inside, you'll find a spacious living area featuring a large TV, pull-out sofa, and two comfortable chairs, ideal for relaxing after a day at the beach.

Registration Number: 260250050092, TA-121-578-0864-01, GE-121-578-0864-01

• 1 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Honolulu

from $309 

View Property   Book Direct

Luxury Top-Floor Ocean View Condo at Kahala Beach

This highly desirable top-floor unit at Kahala Beach offers breathtaking views of the koi pond, sky, and stars. The spacious lanai faces the afternoon sun and sunset, providing a perfect spot for relaxing or entertaining. Its top-floor location ensures peace and quiet, making it one of the most tranquil apartments in the complex.
Registration Number: GE-003-036-7744-01, TA-003-036-7744-01, 1350230020145

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Honolulu

from $326 

View Property   Book Direct

The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood

The Kahala Mansion offers a luxurious, private escape on Kahala Avenue, just steps from the beach. This grand estate features expansive indoor and outdoor living spaces, lush courtyards, and elegant accommodations. Perfect for serene retreats, grand celebrations, or corporate events, the property combines architectural brilliance with resort-style amenities including a private pool, entertainment center, and dedicated concierge services.
Registration Number: GE-132-155-2896-01, TA-132-155-2896-01, 350040280000

• 5 bedroom
• 5 bathroom
• Sleeps 12

Hawaii> Honolulu

from $7,107 

View Property   Book Direct

Kahala Zen Honolulu Monthly Rental with Studio Cottage

This stunning property, Kahala Zen, offers a blend of historic charm and modern comfort in the prestigious Kahala neighborhood of Honolulu. Built in 2024, this newly constructed home features vaulted ceilings, paved walkways, and an open floor plan that emphasizes indoor-outdoor living.
Registration Number: 350040310000, GE-183-524-3008-01, TA-183-524-3008-01

• 5 bedroom
• 4 bathroom
• Sleeps 10

Hawaii> Honolulu

from $852 

View Property   Book Direct

Kahala Beachfront Villa Honolulu - Luxury 2BR Condo

This stunning Kahala Beachfront Villa offers a perfect blend of luxury and tranquility in Honolulu. This fully furnished two-bedroom, two-bathroom condo comfortably accommodates up to six guests, making it ideal for families or small groups seeking a relaxing Hawaiian getaway.

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

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Honolulu

from $362 

View Property   Book Direct

Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast

This stunning beachfront estate in Kahala offers the perfect blend of modern luxury and old Hawaiian charm, ideal for large groups seeking privacy and comfort. Located directly on Kahala Beach, the property features seven air-conditioned bedrooms, each with California king beds, en suite bathrooms, and smart TVs.
Registration Number: TA-104-487-9872-01, 350060190000, GE-104-487-9872-01

• 7 bedroom
• 8 bathroom
• Sleeps 14

Hawaii> Honolulu

from $6,147 

View Property   Book Direct

Luxury Hawaii Estate in Honolulu's Black Point

5-bathroom estate nestled in Honolulu's prestigious Black Point neighborhood. 33-acre lot, this custom-designed retreat combines modern luxury with island charm. The lush tropical landscaping, Diamond Head views, and complete privacy make it an ideal destination for families, groups, or discerning travelers seeking a luxurious Hawaiian escape.

Registration Number: 350020170000, TA-167-134-8224-02, GE-167-134-8224-01

• 5 bedroom
• 6 bathroom
• Sleeps 12

Hawaii> Honolulu

from $2,043 

View Property   Book Direct

Luxury 5BR Oceanview Villa in Kahala, Oahu

5-bathroom villa in Kahala offers the perfect blend of luxury, comfort, and tranquility on Oahu. Located just minutes from the iconic Diamond Head State Monument and close to Kaaiawai Beach, this property provides a serene retreat with easy access to Honolulu's vibrant city life.

Registration Number: 310400040001, TA-076-121-8560-01, GE-076-121-8560-01

• 5 bedroom
• 5 bathroom
• Sleeps 10

Hawaii> Honolulu

from $2,258 

View Property   Book Direct

Luxury Oceanfront Home Near Diamond Head with Modern Design

FEATURED IN ARCHITECTURAL DIGEST MAGAZINE! Step into this exceptional oceanfront residence, a true modern diamond in the rough, offering an unparalleled blend of luxury, design, and tranquility. Perfect for relaxing getaways or entertaining, this property boasts a penthouse atmosphere with expansive ocean views and direct beach access.
Registration Number: GE-092-683-8784-01, TA-180-161-9456-01, 31040027

• 4 bedroom
• 4 bathroom
• Sleeps 8

Hawaii> Honolulu

from $4,758 

View Property   Book Direct

Pet-Friendly Waikiki Studio Near Beach and Attractions

Experience the ideal Waikiki stay in this charming, fully furnished studio that combines comfort and convenience. Located in a highly walkable and safe neighborhood, this property offers easy access to Waikiki Beach, the International Marketplace, Diamond Head Hiking trail, and numerous restaurants and shops.
Registration Number: no, TA-124-162-4576-01, GE-124-162-4576-01, 31012073

• 1 bedroom
• 1 bathroom
• Sleeps 2

Hawaii> Honolulu

from $125 

View Property   Book Direct

Kahala Oasis Luxury Vacation Home in Honolulu

5-bathroom luxury retreat nestled on the prestigious Kahala Avenue in Honolulu, Hawaii. This expansive estate comfortably hosts up to fourteen guests, blending elegance, comfort, and privacy amidst lush tropical landscaping. The property features a tropical pool and spa paradise, with a cascading waterfall pool and a large heated Jacuzzi spa perfect for relaxation and family gatherings.
Registration Number: 1350070050000, TA-153-997-3120-01, GE-153-997-3120-01

• 6 bedroom
• 6 bathroom
• Sleeps 12

Hawaii> Honolulu

from $1,129 

View Property   Book Direct

Luxury 5BR Kahala Home with Pool and Ocean Views

This stunning five-bedroom, four-bath home in the upscale Kahala neighborhood offers the perfect blend of island and Balinese design, providing a luxurious retreat for up to 14 guests. The expansive 20,000-square-foot property features incredible outdoor spaces, including a private pool, lush tropical landscaping, and ample outdoor seating for dining or relaxing under the shaded lanai.
Registration Number: TA-048-116-5312-01, GE-048-116-5312-01, 350080310000

• 5 bedroom
• 4 bathroom
• Sleeps 14

Hawaii> Honolulu

from $1,938 

View Property   Book Direct

• «
• 1
• »

Showing 1 of 1 pages.