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Oahu Luxury Vacation Rentals & Villas

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

Our luxury Oahu vacation rentals span the island, offering a wide variety of choices to travelers seeking that perfect Oahu getaway. You’ll find rentals and villas that exude both the comfort of a private home, but with the posh amenities so deserved when you finally take a break from your busy life. From chef’s kitchens to private lanais overlooking the Pacific, concierge services to arrange your family’s activities to infinity pools, these dream residences make every aspect of vacation a dream. From Diamond Head, known for its posh West Coast feel, to the quieter, more residential feel of Hawaii Kai, Gather’s Oahu vacation rentals truly offer something for everyone. Browse all Oahu vacation rentals below, or choose your favorite Oahu destination to hone in on that perfect location.

Discover popular Oahu destinations

Aina Haina | Diamond Head | Hawaii Kai | Kahala | Kailua | Kaka’ako | Ko Olina Beach Resort| Kuilima Estates | Lanikai | Makaha | North Shore | Turtle Bay | Waikiki | Waimanalo
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    Aerial shot of the pool. Welcome to Makalei, your tropical oceanfront home away from home. Lounge poolside with a cool drink and enjoy Hawaii! Enjoy a relaxing day by the pool with a cool drink. Lounge in the bright living area with an open layout and seamless indoor-outdoor flow. Seamless indoor-outdoor connection in the living area leading to the beach. Spacious living area with an open design that blends indoor and outdoor spaces.

New Listing!

Makalei

5 Beds
5 Baths
10 Sleeps

Starting at $916/night

    Relax by the pool at twilight, a peaceful spot to enjoy a drink. The cozy cabana by the pool is an added touch of privacy and relaxation. Enjoy time on the main floor lanai with ocean views. Unwind in the primary suite's lanai with ocean views and fire pit. Cozy up around the fire table on the primary suite lanai as twilight sets the perfect ambiance. Prepare meals on the spacious kitchen area featuring top tier appliances and panoramic ocean views. The kitchen’s inviting design features an island, modern appliances, and ample storage, creating a perfect space for meal prep or casual gatherings.

New Listing!

Leaf House

5 Beds
4.5 Baths
10 Sleeps

Starting at $750/night

    Lush backyard with large pool deck and pool give you all the feels of having your own private mini hotel! (Note: Upper pool area is apart of the pool and NOT a spa) Enjoy the islands cross breeze in the main living-room, complete with pool table and a front porch to watch the basketball players in the group! Dinning room, the perfect place to entertain and dine at the same time! Challenge friends to a game on the sleek pool table, where memories and laughter are guaranteed. Birds eye view of the pool from the media room lanai. (Note: Upper pool area is a part of the pool and NOT a spa) Media room covered lanai Grand primary suite with work out area, private deck and ensuite!

Villa Hui Hou

5 Beds
4.5 Baths
12 Sleeps

Starting at $667/night

    Ocean views from lanai with comfortable seating. Relax and bring your favorite book or enjoy a movie night. Dining and kitchen with ocean breezes. The fully equipped kitchen designed by Roy Yamaguchi with panoramic views. The lanai pocket doors open up to seamless indoor /outdoor living. Stainless steel appliances for your culinary adventures. An open floor plan for entertaining.

Holiday Availability

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Ko Olina Beach Villas B410

2 Beds
2 Baths
6 Sleeps

Starting at $800/night

    Enjoy the seamless flow between the kitchen and dining area with seating and expansive views. Welcome to Ko'Olina Beach Villa O1006 - your luxury resort residence in Oahu! A spectacular view of the ocean and golf course from the lanai. Elegant open-concept living with dining and lounge areas, overlooking a stunning twilight ocean view. The living room area with comfortable seating and TV. An open kitchen with stainless steel appliances and bar seating. Cozy lanai setup with a view, adjacent to a sleek open kitchen.
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Ko Olina Beach Villas O1006

2 Beds
2 Baths
6 Sleeps

Starting at $600/night

    Welcome to Ko'Olina Beach Villa B107 - your luxury resort residence on Oahu! Enjoy your morning coffee on this cozy lanai. The lanai pocket doors open up to seamless indoor outdoor living The spacious Kitchen with bar seating that opens to a large lanai. The kitchen features stainless steel appliances and lovely views. Kitchen island/bar for quick meals or cheers. The dining areaa has the most incredible views and island breezes.
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Ko Olina Beach Villas B107

3 Beds
3 Baths
6 Sleeps

Starting at $725/night

    The incredible ocean views from the lanai. Open concept floorplan with a seamless blend of living, dining, and kitchen areas, giving you a spacious yet connected space. Enjoy the sea breezes in the open floor plan with bar seating in the kitchen. Cozy afternoon view from the lanai. The bar seating in the kitchen area for quick meals or entertainment. Seamless flow between the living, kitchen and dining areas. The kitchen features stainless steel appliances and opens up to a living area for easy entertaining.
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Ko Olina Beach Villas B602

2 Beds
2 Baths
4 Sleeps

Starting at $450/night

    Welcome home! An elegant entrance to you tropical home. Lounge in the upper-level living area featuring the woven bamboo ceiling with ceiling fan, the wicker sofas with thick, comfortable white cushions and TV, giving the room a tropical and relaxed vibe. The living area features seamless indoor-outdoor living with access to the spacious wrap-around deck, perfect for taking in the surrounding views. Relax outdoors featuring the hot tub with garden views. The deck provide ample space for outdoor dining and relaxation, with a gas grill for barbecues. The wrap around deck with outdoor dining is accessible through the living area.

New Listing!

Kealoha Tropical Beach Villa

4 Beds
2.5 Baths
8 Sleeps

Starting at $350/night

    Dive into serenity with ocean vistas and Diamond Head glimpses! Your dream escape in every corner. Vacation perfected. Step in and embrace the island's beauty! Feast for 10, framed by stunning vistas! Take a dip in the crystal clear pool. Discover and get cozy inside your tranquil retreat! Seamless transition from the living room to lanai and pool.
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Aloha Nalu

4 Beds
3.5 Baths
10 Sleeps

Starting at $817/night

    Breathtaking ocean views from your expansive lanai Outside Ko Olina Beach Villas B609. Enjoy your open floor plan, bar seating and soft ocean breezes. This picture looks in to the kitchen with stainless steel appliances, and the living and dining area. Bright and cheerful dining in your abode. Plenty of room for hosting and relaxing. The comfortable living space and TV for your favorite shows. The primary guest bedroom with comfortable linens and lovely vacation views.

Holiday Availability

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Ko Olina Beach Villas B609

2 Beds
2 Baths
6 Sleeps

Starting at $748/night

    A grand lanai with the panoramic views of your dreams! You have ocean views and ocean breezes from the kitchen and living areas. This fully equipped kitchen with stainless steel appliances will please any chef! Enjoy the breakfast bar while sipping your coffee. An open floor plan for visiting between the kitchen and dining area. A flat screen TV for movie night on the island. This tastefully appointed home is all your on your next getaway.
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Ko Olina Beach Villas O402

3 Beds
2.5 Baths
6 Sleeps

Starting at $451/night

    Private oceanfront lanai at your Ko Olina Beach Villa B109 for perfect sunsets. Tall ceilings and open concept design blends living, dining and kitchen areas. 1.Tall ceilings and open concept design blends living, dining and kitchen areas. Expansive counters and gourmet appliances make meal preparation a pleasure. 2.Expansive counters and gourmet appliances make meal preparation a pleasure. A spacious and airy living area with a dining table and lounge, opening up to ocean views. 3.A spacious and airy living area with a dining table and lounge, opening up to ocean views.
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Ko Olina Beach Villas B109

2 Beds
2 Baths
6 Sleeps

Starting at $900/night

    Beautiful lanai with patio seating and table, and perfect Pacific views. Bright kitchen with island, bar seating and breathtaking views. Stainless steel appliances and a wine cooler for the culinary best! Relax and dine while ocean breezes fill the air. The ocean view from the lanai. Enjoy your morning coffee on the lanai. Plenty of seating and ambient lighting in the open concept living areas.
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Ko Olina Beach Villas O1004

2 Beds
2 Baths
4 Sleeps

Starting at $500/night

    Welcome to Ko'Olina Beach Villa OT414 - your luxury resort residence on Oahu! Seamless living in the beautifully furnished living room that overlooks the kitchen and dining room Open an inviting indoor-outdoor living space with ocean and mountain views Kitchen with a view—enjoy culinary creations while overlooking the scenic outdoors Kitchen island/bar for quick meals or cheers. Fully-stocked kitchen with everything you need to whip up a delicious meal while on vacation Alternate View of Kitchen with top of the line appliances and breakfast bar
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Ko Olina Beach Villas O414

2 Beds
2 Baths
6 Sleeps

Starting at $385/night

    Welcome to Mokuleia Beach Villa, your tropical home away from home in Hawaii! Enjoy al-fresco dining experience with ocean views and tropical breezes on the expansive deck. Relax in the living area with large windows and ocean views. Enjoy seamless flow from the kitchen to the living area, perfect for gathering while taking in the ocean views. Relax in the living area with large windows and ocean views. Gather around the spacious kitchen island, perfect for casual meals or entertaining. Savor the views from the living area.

New Listing!

Mokuleia Beach Villa

4 Beds
3 Baths
8 Sleeps

Starting at $260/night

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