5 Best Vrbo Vacation Rentals In Oahu East Shore, Hawaii - Updated 2024

| 4 min read

Away from the touristy hubbub of Waikiki, East Oahu Shore offers the quintessential Hawaiian experience with pristine beaches, verdant surroundings, and incredible natural wonders. Around 30 minutes away from Honolulu, East Oahu is a mix of peaceful neighbourhoods and breathtaking vistas. There is much to explore here including Halona Blowhole lookout, Lanikai Beach, Waimanalo Beach Park Hanauma Bay, and thrilling outdoor activities. Choosing vacation rentals on this side of Oahu will put you right in the midst of Hawaiian paradise. So if you are looking for quieter, close-to-nature stay options, then those in Oahu East Shore will definitely be a great choice. Listed here are the best Vrbo accommodations in Oahu East Shore, Hawaii.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 04, 2024.

1. Hale Pulelehua (from USD 256)

Score the amenities akin to a private pool villa with a stay at Hale Pulelehua, a gorgeous vacation rental in Kailua. The large property’s main draw is its beautifully landscaped yard, which offers endless opportunities for splashing fun in the private pool. Apart from spacious bedrooms conducive for big families or groups, it also comes with modern indulgences such as free WiFi, cable TV, and a fully stocked kitchen.

The location is a knockout as you’ll be staying in a spot just a five-minute stroll to the access going to Kailua Beach. And if you don’t want to miss out on the downtown thrills, you’ll be glad to know that the home is just a five-minute drive to the heart of Kailua filled with shops and restaurants galore.

Stayed at this property?
Kailua, Hawaii, United States
17.76 km (11.1 mi) from Diamond Head State Monument
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

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2. Charming cottage close to the beach (from USD 145)

For the family to enjoy a breezy escape, why not spend the holiday in this charming Vrbo beach house in Oahu? This tropical-style cottage provides ample spaces for small troops to lounge and relax. It is readily equipped with WiFi, smart TV, boogie boards, and beach equipment to cater to your group’s kind of fun. Families are most especially welcome as the unit is equipped with a highchair, baby monitor, and a travel crib.

The outdoor space of this Vrbo vacation rental in Waimanalo is made more inviting by having a sizeable lanai with a gas grill for cookouts. There’s also a fenced play area for the kids and an outdoor shower to help you wash off the sand after hitting the beach, which is around 274 meters (898.95 feet) away.

Stayed at this property?
Waimanalo, Hawaii, United States
13.65 km (8.5 mi) from Diamond Head State Monument
cottage 4 Guests 2 Bedrooms 2 Bathrooms

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3. Smart guesthouse close to attractions (from USD 176)

Compact and beautifully-furnished, this guest house offers sweeping views of the ocean, marina, as well as mountains. Recently constructed, the small Hawaiian cottage rental adjoining the main house is located in an exclusive neighbourhood in Hawaii Kai, close to attractions such as Hanauma Bay and Sandy Beach.

Both the comfy open-concept living room and the master bedroom offer unending views that soothe the soul. This two-bedroom vacation rental in Oahu is also equipped with a pull-out sofa, making it a comfortable retreat for medium-sized groups. To top it off, the house comes with a cute side garden and a deck where you can luxuriate in the beautiful Hawaiian weather and vistas.

Stayed at this property?

11.24 km (7.0 mi) from Diamond Head State Monument
169 reviews   Wifi Available
House 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5
Minimum Nights: 30
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The only issue is that we didn't read the listing carefully: the second bedroom is open to the living room (with sofa bed) and kitchen
You definitely don't need to use the air conditioning and it open the windows for a delightful breeze
All these warrant five stars
Plus side is there was a cooling breeze every night and we hardly needed to use the ac
The kitchen is well-stocked and there's a Safeway grocery store down the hill
The apartment is clean and beautifully situated
Amazing views and super convenient location Loved how clean and organized everything was
Everything we were looking for and More
There are beach chairs boogie boards beach towels and snorkels for use as well
she was fantastic and easy to communicate with
He was very communicative and helpful even suggesting places to eat on the Big Island
We really enjoyed the property and Claudia was the greatest person very friendly and helpful
The guest home was lovely
Beautiful views immaculate property and the kindest of hosts
boogie boards snorkeling gear
Spectacular views convenient location
This is a great location if you want to see the island and stay away from the crowds of Waikiki
so the location was ideal
Wonderful location and a very nice condo
Read more reviews
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4. Large two-story cottage close to beach (from USD 520)

Located virtually on the beach, this cottage is a dreamy option for a beach getaway. Inside, the cottage is simple yet roomy and bright. Furnished neatly, it comes fitted with all essential amenities including newly installed ACs in the bedrooms, TV with cable, and a full kitchen. The house incorporates two bedrooms and two extra beds, so up to four guests can be easily accommodated.

Outside this beachfront vacation rental in Oahu, you will find a verdant and colourful garden offering stunning ocean views and access to a semi-private dock. Chill out in the deck chairs or swing chairs enjoying the sound of waves, or take a soak in a hot tub under the stars.

Stayed at this property?
Waimanalo, Hawaii, United States
15.05 km (9.4 mi) from Diamond Head State Monument
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
the house is cozy and immaculate The outdoor living room is a gorgeous backdrop for meals and relaxing
The small beach with a short stair access was perfect for a private swim Hot outdoor shower and hot tub round out the experience
the property description says IS TRUE
The house and kitchen were spotless and had everything you could need
The bungalow is very private well-appointed and includes so many little extras that show a high level of hospitality and consideration for guests
Also the door lock does not automatically lock when closed
The owner took us on his boat for a awesome ride
You can not go wrong with renting this property
This house and beach was wonderful for our entire family
Hot tub was perfect and crystal clean
Yet another awesome stay at Makapu'u Hale :)
The views were great and the location was ideal for the local beaches
Being right on the water so close to snorkeling was a dream
Makapu'u Hale is a secret garden perched over a gentle turqupise slice of the Pacific Ocean Surrounded by a beautifully maintained garden
This property is one of the best we've ever rented for many reasons
Read more reviews
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5. Spacious well-furnished oceanfront house

A great choice for families and big groups, this huge house has four bedrooms sleeping 12, three bathrooms, a generously-sized living/dining space and a fully functional kitchen. Spread over two floors, the house is well furnished, bright and airy, and is fitted with a wide range of amenities. The house is literally on the Waimanalo Beach offering incredible views of the ocean. You will also have access to a huge yard that comes with a variety of furniture, a hot tub, and even a tree house! Honolulu and other attractions are around 30 minutes’ drive away.

Stayed at this property?
Waimanalo, HI, US
15.4 km (9.6 mi) from Diamond Head State Monument
98 reviews  
House 12 Guests 0 Bedrooms 0 Bathrooms
Oops, this listing is currently inactive. Check out these alternative properties in the same location.
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Appreciate Oahu East Shore's local flavour

Staying at a vacation rental offers an opportunity to enjoy Hawaii up close. Along with being reasonably priced, these houses give you enhanced privacy, flexibility, and comfort. You even get beach accessories included in the rental! However, do keep in mind the distances involved–if you stay away from the city centre you will need to have access to a car. Additionally be sure to consider the safety of the neighbourhood before finalizing your booking to Oahu East Shore with these great Vrbo accommodations.

Stayed at this property?

Frequently asked questions about the Vrbo accommodations in Oahu East Shore, Hawaii

1. Which Vrbo vacation rentals in Oahu East Shore have a pool?

If you’re keen to still enjoy a splashing time in Oahu when taking a break from the beach, you can check out Hale Pulelehua. This gorgeous vacation rental features a private outdoor pool at your disposal.

2. Which Vrbo vacation rentals in Oahu Island have parking?

To secure a guaranteed parking space at your accommodation, make sure to book a stay at: i) this smart guesthouse close to attractions, ii) this large two-story cottage close to beach, iii) Hale Pulelehua, or iv) this charming cottage close to the beach.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Writing and travelling both bring joy to Sowmya's life. Her favourite destination so far is Bhutan - a land of incredible beauty! And her favourite style of travelling is solo backpacking!...Read more

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