Last Updated August 9, 2021 8/9/2021

15 Most Dreamy Oahu Vacation Rentals

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There’s a good reason so many people talk about quitting their jobs and fleeing to the Hawaiian Islands: it’s truly the definition of paradise. Dazzling blue waters, world-famous beaches, wonderful sunsets and some of the best surfing spots all club together to offer an invitation into happiness. And Oahu, home to the state capital of Honolulu, comes out at the top when showing you just how it’s done.

Come here to chill out on Waikiki Beach, to get up close and personal with the turtles swimming by, to wander through palm-tree-lined streets, and to decide whether you do actually need to return home at the end…or whether you can just stay here forever instead. Read on for some of our top places to stay while you’re enjoying this magical island.

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Beach Level Studio Direct Ocean Views
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Dining area of Villa 105

Beach Level Studio Direct Ocean Views

Located a mere 50 yards from the flower-adorned swimming pool and 30 yards from the sandy beach, this ocean-front villa is a perfect place for anyone who dreams of waking up with stunning views. A beautiful spot that’s colorful both inside and out, it’s home to one bedroom and one sleeper sofa bed, suitable for up to four guests. You won’t know whether to spend your time inside or outside here, with luxury gel memory foam mattresses in the bedroom and living room, a Bose Entertainment System with a 55” Smart TV, and a gourmet kitchen. Outside, there’s a huge lanai overlooking the ocean. This villa is also set inside a resort, which means it comes with access to a heated pool and jacuzzi, helicopters, horseback riding, and the on-site Lei Lei’s Bar & Grill.

Stunning Oceanfront Estate with Private Pool & AC: Hale Makai at Diamond Head
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Swimming pool at Stunning Oceanfront Estate

Stunning Oceanfront Estate with Private Pool & AC: Hale Makai at Diamond Head

The famed Diamond Head Crater makes for a breathtaking backdrop to this luxury oceanfront estate, with three bedrooms, three and a half bathrooms and plenty more living space throughout. A brilliant vacation rental situated in the south of the island, its grassy backyard offers a great contrast of colors and activities against the deep blue sea views. You’ll want to spend at least a few hours sunbathing in the backyard, with the gentle splash that comes from waves hitting the wall. Hawaiian aesthetic seamlessly flows throughout the bedrooms with king-size beds, through to the common area and outside spaces. There’s a private pool and BBQ for spontaneous family parties and access to bikes, floaties, and boogie boards inside the garage for all kinds of fun.

A View to Die For, 3-Bedroom on Waikiki Beach
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A View to Die For, 3-Bedroom on Waikiki Beach

A View to Die For, 3-Bedroom on Waikiki Beach

Floor to ceiling glass offers a spectacular view over Waikiki Beach at this three-bedroom Airbnb. A place that takes “beachfront living” to the next level, this is the only privately-owned condominium in Waikiki where you can step right from the building onto the sandy beach. Before you’ve given into your urges and dipped your toes in the water, you can admire those same views from the extensive balcony overlooking the ocean, or even while you’re eating breakfast in the kitchen or tanning on the sun beds. A fully-stocked kitchen brings all of your “digging into a feast while staring at the ocean” dreams to life, and huge, sweeping bedrooms with a mix of king size and single beds make this spot perfect for families.

Luxury Yacht Rental in Beautiful Hawaii
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Vida Mia yacht mid journey around Oahu

Luxury Yacht Rental in Beautiful Hawaii

The historic Vida Mia yacht might not technically be situated on Oahu island itself but it overlooks the island in the best way possible. Offering the chance to experience Hawaii from a whole new perspective, this luxury yacht isn’t significantly more expensive than on-land accommodation on the island and comes with the added benefit of waking up to the gently rocking water below you. Two bedrooms give space for up to seven guests (with one king-size bed, and two bunk beds) and there are three additional settees outside under the covered deck. When this fancy yacht isn’t cruising around the Hawaiian coastlines, she resides at Ala Wai Harbor. But, when you’ve claimed her as yours for a couple of nights, she’s free for coastal cruises along the Waikiki Shoreline.

Oceanfront Bliss with Epic View, Gourmet Kitchen & Lanai
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Living space at Oceanfront Bliss Airbnb

Oceanfront Bliss with Epic View, Gourmet Kitchen & Lanai

A home away from home with gorgeous Diamond Head and Pacific views in every direction, this two-bedroom Airbnb with space for six guests is a brilliant family vacation spot with high-end touches dotted throughout. Tropical meets classical here when it comes to decor, with the additional benefits of stylish, state-of-the-art amenities throughout and super cozy beds. Within walking distance to the resort’s best beach activities, restaurants, nightlife, and cultural activities, it’s a comfortable haven to return to at the end of your busy day. And, when you get back after exploring the island, you can choose between updating your friends on the super-fast WIFI, chilling out watching TV, preparing meals to share on the private lanai, or just taking in the incredible views in front of you.

Beachfront Hawaiian Private Villa
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Beachfront Hawaiian Private Villa

Beachfront Hawaiian Private Villa

While some vacation rentals in Oahu might struggle with a lack of space, this premium, beachfront rental is more than confident in its guarantee to have enough room for all. It has space for up to 25 guests, which makes it the perfect Hawaiian Vrbo for extended family holidays, long-overdue catch-ups, or just any group who doesn’t want to step on each others’ toes. Nestled along the beautiful Kailua beach, it features an open-plan living and dining area, a fully stocked kitchen, double beds, and plenty of outdoor space. Outside, you’ll find a hammock, sunbeds, and almost endless grass.

Direct Oceanfront @ Waikiki Beach Tower
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Living area and dining table at Waikiki Beach Tower

Direct Oceanfront @ Waikiki Beach Tower

You’ll spot a little of everything when it comes to decor styles at this two-bedroom, Waikiki beachfront Airbnb. Head to the living space for turtle-themed interiors bringing out some of the best that Hawaii has to offer, or step inside the bedrooms for a more traditional blue and white approach. The bathroom comes in a super sleek classical style with a freestanding tub and jet black tiling. Located only steps away from the beach, it’s recently refurbished and comes with all of the trimmings for a laid-back adventure in Oahu. A large lanai and ocean views from every room just add to the relaxation you’ll feel when staying here.

Pupukea Home on 1 Acre with Mountain & Ocean Views
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Outdoor seating with ocean views at Pupukea Home

Pupukea Home on 1 Acre with Mountain & Ocean Views

You’ll struggle to know what to look at first when you check into Pupukea Home. With mountain views in one direction and ocean views in the other, it’s a place surrounded by tranquility no matter which room you’re in. Set on an acre of land, it’s home to three bedrooms and has space for up to 10 guests. Attention to detail here is the key to making this spot feel like home, even if you’re only checking in for a few days. Its kitted-out kitchen, wooden decor, comfy beds and open plan style make this undoubtedly one of the most welcoming Vrbos in the area. It’s also set in a great location for exploring Oahu’s best parts: 10 Minutes to historic Haleiwa Town, five minutes to Waimea Bay for summertime snorkeling and swimming, and 10 minutes to Turtle Bay Resort Championship Golf Course.

Hale Ohana - Luxury Villa with Infinity Pool, Beachfront
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Hale Ohana - Luxury Villa with Infinity Pool, Beachfront

Hale Ohana - Luxury Villa with Infinity Pool, Beachfront

Hale Ohana is the Oahu vacation rental of dreams. A luxury villa, infinity pool overlooking the ocean and beachfront location are just some of the staple reasons you’ll want to spend a few nights here. Six bedrooms mean there’s plenty of space for up to 20 guests, making this an ideal spot for large gatherings or celebrations in Oahu. The open-air feel of this villa just adds to its spaciousness, with a range of amenities that are just as gorgeously oversized as the place itself. Rooms come with king-size beds, the upstairs recreation room is kitted out with comfy beanbags and a large TV and there’s even more room downstairs.

2-Bedroom Ilikai Suite with Stunning Ocean Views
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Living area at Ilikai Suite

2-Bedroom Ilikai Suite with Stunning Ocean Views

This two-bedroom condominium is modern and stylish; the perfect getaway for anyone who appreciates interiors as much as they do the incredible exteriors and magical views. A treat for the eyes with its laid-back decor, this stunning ocean view Airbnb sits high up on the 13th floor, offering panoramic views of the ocean from every room. Its fully stocked kitchen means you’ve got everything you need to cook up a storm, which is best enjoyed sat on the balcony. Located close by to the bustling life of the Waikiki strip and with optional parking nearby, it covers far more than all of the essentials.

Contemporary Estate in the Heart of Honolulu
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Contemporary Estate in the Heart of Honolulu

Contemporary Estate in the Heart of Honolulu

Less a typical vacation rental and far more a huge, impressive estate, this luxury property has room for 24 guests to fully enjoy everything it has to offer. Unobstructed ocean views set on a verdant hillside with almost endless amenities mean that you’ll never want to leave. Check-in here without the worry that you’ll run out of things to do: there are more than 6000 square feet of living space, all of which are covered with the property’s Bose Surround Sound System. Surfboards and beach gear are offered free with the property, which you can make the most of on the nearby beach, only five minutes away. Half of the fun of staying here comes from simply exploring the place.

Turtle Bay Beachfront Villa
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Sunny terrace at Turtle Bay Beachfront Villa

Turtle Bay Beachfront Villa

It’s the vibrant colors that you’ll notice first when you check into this Turtle Bay beachfront villa. Closely followed by the luxury facilities inside; namely the Panasonic massage chair, the queen sleeper sofa that turns into an enormous flat area for a family to watch and enjoy movies in, and the deluxe 55” flat-screen TV. Between wandering around and admiring all of the amenities, and staring out the windows at the rolling ocean views in front of you, this Airbnb is fully equipped to keep you breathless throughout your entire stay. There’s space for up to eight guests across three bedrooms, and a spacious living area where everyone can hang out together.

Estate with Ocean & Mountain Views, Beach Across the Road
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Exterior view of New North Shore Estate

Estate with Ocean & Mountain Views, Beach Across the Road

A property that’s renowned for booking up quickly months in advance, this four-bedroom Vrbo offers both mountain and ocean views, in an airy North Shore estate with plenty of room for fun. Located inside a quiet, gated community, it bridges the gap between having nature on your doorstep and being securely protected at all times. It’s perfect for family getaways with young children, who can make the most of the greenery surrounding the property while adults enjoy what’s inside. Dinners here come with surrounding spectacular views and you can cook up a feast on the granite island. A futon, lounger and hammock all sit outside in the sunshine, overlooking the property’s hot tub. There’s even an outdoor (but enclosed) shower to rinse off before you head inside at the end of the day.

Turtle Bay Getaway - Newly Renovated
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Living space at Turtle Bay Getaway

Turtle Bay Getaway - Newly Renovated

Neat and comfortable, this Turtle Bay apartment sits on the north shore of Oahu and offers space for five guests inside two bedrooms. It’s modern yet relaxed; a place where you’ll feel comfortable throwing off your shoes and settling into the comfy sofas after your day of making the most of this property’s surfboards and beach equipment. This condo is also just steps from a swimming pool, tennis courts and a pavilion, which means adventure is never too far away from your bed. If you’ve come to Oahu to do some exploring of the island, this is a great Airbnb to fulfill all of the activities you have in mind.

Waimanalo Beach Cottages
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Exterior shot of cottages

Waimanalo Beach Cottages

Traveling in a large group but still fancy having your own space? This Vrbo ticks off all the boxes, offering a range of cottages (and a discount if you book them all) only steps from beautiful Waimanalo Beach and the incredible sunsets it offers every evening. Between all nine cottages, this Vrbo has space for 24 guests. Each cottage comes complete with a kitchen and dining table, indoor and outdoor living areas, and cozy bedrooms with double beds. Roomy terraces with seats act as your new favorite spot for starting a new book or enjoying a morning coffee. This family-owned business is known for its attention to detail, with all of the trimmings necessary for a memorable trip.

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