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Kahala Luxury Vacation Rentals & Villas

Start Your Vacation Rental Search > Hawai’i Vacation Rentals and Villas > Oahu Luxury Vacation Rentals & Villas > Kahala Luxury Vacation Rentals & Villas

Popular Oahu neighborhoods

Aina Haina | Diamond Head | Hawaii Kai | Kailua | Kaka’ako | Kuilima Estates | Lanikai | Makaha | North Shore | Turtle Bay | Waikiki | Waimanalo
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The average night price is $1,896

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    Tropical backyard with lush greenery and a sparkling pool. Cozy outdoor seating area with picturesque mountain views. Serene balcony overlooking vibrant palm trees. Grand entrance surrounded by tropical landscaping. Bright and spacious living room with natural light. Open family room with elegant design and large windows. Stylish seating area with a festive Christmas tree centerpiece.

New Listing!

Pili Pono

5 Beds
6.5 Baths
12 Sleeps

Starting at $667/night

    Relax in the serene courtyard surrounded by lush greenery. Spacious covered patio, perfect for outdoor dining and entertaining. Private driveway and courtyard entry for a peaceful retreat. Open-concept dining area with 8 comfortable seats, perfect for group meals. Gourmet kitchen with stainless steel appliances and a large island. Cozy living room with comfortable seating and a view of the outdoors. Bright and inviting living room with vaulted ceilings and natural light.

New Listing!

Kahala Zen

5 Beds
4 Baths
10 Sleeps

Starting at $500/night

    Grand Entrance to the Kahala Mansion Spacious living area with high ceilings, natural light, and luxurious furnishings for a warm and inviting atmosphere. Stunning fireplace with intricate stonework, creating a cozy and elegant focal point. Serene courtyard with a central fountain, lush landscaping, and sunset views for a tranquil ambiance. Sparkling pool surrounded by Mediterranean-inspired architecture, perfect for relaxing or entertaining. Beautiful courtyard with manicured lawns, a fountain, and inviting pathways, ideal for outdoor gatherings. Open courtyard space with elegant features and a peaceful atmosphere, perfect for unwinding.

The Kahala Mansion Event Venue

5 Beds
5.5 Baths
12 Sleeps

Starting at $5,500/night

    Pool and Cabana towards Home Kitchen Oceanfront lawn test Oceanside Yard with Moonrise test Pool and Cabana toward Ocean Front Courtyard Front Entrance
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Banyan House

8 Beds
9.5 Baths
16 Sleeps

Starting at $4,606/night

    Luxurious pool area with views of the beach Pool deck, with plenty of lounge options Enjoy complete privacy in a fully gated property Entry foyer and staircase to upper floor Indoor/outdoor bar seating for seven guests Living room area, looking makai (toward the ocean) Living room area, looking mauka (toward the mountains)
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Kahala Beachside Estate

7 Beds
8 Baths
14 Sleeps

Starting at $2,667/night

    Pool and Cabana toward Ocean Pool and Cabana towards Home Oceanfront lawn Front Courtyard Front Entrance Great Room Great Room
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Banyan House 4 Bedroom

4 Beds
5.5 Baths
8 Sleeps

Starting at $3,500/night

    Grant Entrance to the Kahala Mansion Spacious and comfortable formal living area with modern sofas perfect for gatherings. Elegant stone fireplace with a warm, inviting glow, perfect for cozy evenings indoors. Tranquil backyard with paved lanai area. Private pool flanked by vibrant tropical flowers. Tranquil backyard with paved lanai area. Tranquil courtyard featuring lush greenery, a central fountain, and a serene ambiance for relaxation or gatherings.

Private Pool

The Kahala Mansion

5 Beds
5.5 Baths
12 Sleeps

Starting at $2,833/night

    Kahala Mini Resort Primary bedroom Primary bathroom Primary bedroom lanai Guest bedroom Guest bathroom Guest bedroom

Kahala Mini Resort*

7 Beds
7.5 Baths
14 Sleeps

Starting at $4,250/night

    Luxurious Backyard Lounge Seating on Covered Lanai Game Area with Pool Table Convertible to a Ping Pong Table Front Entry Room Front Entry Room Front Entry Room Dining Room

Kahala Lani

5 Beds
4 Baths
14 Sleeps

Starting at $933/night

    Welcome to Kahala Grand Splendor, the perfect vacation home. Dine with a view in the elegant dining area with table for eight, just steps away from the pool. A large pool with a fountain and an ion cleaning system, providing a chemical-free pool experience. Twilight views from the pool! Relax and dine in the open-concept living and dining area with beautiful poolside views. Enjoy the spacious and elegant living area, perfect for gatherings and relaxation. Prepare meals with ease in the modern and fully equipped kitchen with garden and pool views..

Kahala Grand Splendor

5 Beds
4.5 Baths
10 Sleeps

Starting at $833/night

    Beautiful garden featuring a private spa surrounded by tropical plants for a tranquil escape. Relax and unwind in the private outdoor spa, surrounded by lush tropical plants and vibrant flowers for a serene retreat. A cozy and spacious living room with vaulted ceilings, plush seating, and abundant natural light, ideal for relaxing with family and friends Stylish sitting area under high, vaulted ceilings—perfect for enjoying coffee and conversation Fully equipped gourmet kitchen with professional-grade stovetop and spacious design for cooking enthusiasts Inviting lounge area with comfortable couches, perfect for gathering and enjoying quality conversations Elegant dining room with seating for 6, featuring warm lighting and charming interiors for memorable meals

New Listing!

Kahala Palms

4 Beds
3.5 Baths
8 Sleeps

Starting at $655/night

    Back yard, with view of main house TV/family room TV/family room Kitchen and breakfast nook Kitchen and breakfast nook Sitting area off Kitchen Kitchen views!
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Ho'okipa Villa

5 Beds
4 Baths
14 Sleeps

Starting at $360/night

    Aerial view of the lush pool area surrounded by tropical gardens, offering a serene, private oasis. Relaxing poolside lounge area with comfortable seating and umbrellas, ideal for unwinding in the shade. Beautiful pool area surrounded by palm trees and tropical plants, perfect for a relaxing outdoor experience. Enjoy the resort-style pool with a beautiful waterfall feature, surrounded by tropical landscaping for a serene retreat. Outdoor lanai with ample seating, surrounded by lush greenery for an unforgettable alfresco experience. Picturesque entrance pathway lined with tropical plants, welcoming you to your private villa oasis. Stunning grand entrance lobby with high ceilings, marble floors, and elegant decor for a luxurious first impression.

New Listing!

Kahala Oasis

6 Beds
6.5 Baths
12 Sleeps

Starting at $465/night

    Enjoy the morning views on the front living room with pool view. A perfect spot to enjoy your coffee. The view from the primary suite lounge looking to the pool. The primary suite lounge looking at the front living area. Enjoy a relaxing dip in the private pool. The home has an open-concept floorplan allowing seamless flow and connection. Back living and TV room.
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Kahala Cottage

2 Beds
2 Baths
6 Sleeps

Starting at $183/night

    Inviting resort-style pool with crystal-clear waters, framed by a beautifully landscaped garden—your luxury retreat at home. Lanai/Terrace. Lush tropical paradise with a private pool and sun loungers. Sun-drenched backyard oasis with comfortable lounging, perfect for relaxation and entertainment in your private slice of paradise. Welcoming home entrance with tropical landscaping and a spacious driveway. Living Room. Living Room.
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Kahala Breeze

4 Beds
4.5 Baths
8 Sleeps

Starting at $483/night

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