Let’s Go To The Beach: Top 5 HomeAway & Vrbo Rentals In Oahu, Hawaii

Let’s Go To The Beach: Top 5 HomeAway & Vrbo Rentals In Oahu, Hawaii
| 5 min read

The beach is good for the soul. And, what better way to spend your vacation than by going to a place where it always feels like summer? Oahu, the most popular tourist island in Hawaii, offers a refreshing tropical ambiance that welcomes every visitor like a warm embrace.

Once you’re ready to hit the beach, first and foremost, you have to find a vacation home suited for your preferences and needs. We’ve put together a list of your best HomeAway and Vrbo vacation rental options in Oahu. Come and take a look:

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. Dramatic views right from your window: Premier Beachfront Getaway (1,209 USD)

The town of Kailua in Oahu has been consistently voted as one of Hawaii’s premier beach getaways and it’s not surprising why. Turquoise waters, fine white sand, and palms trees … these are all waiting for you in this piece of paradise! Located right on the beachfront, you will enter this property through a private gate that leads to a wide green lawn. Receive a warm welcome from the staff who will make sure that you’ll have a great experience during your vacation. Once you have settled your luggage, it’s time to put your feet up! With this vacation home’s wide spaces, even the biggest of families can fit in and have fun. You can even learn some delicious Hawaiian recipes and prepare them here in the modern kitchen with a wide selection of cooking appliances and utensils. Serve the meals hot and fresh at the adjacent dining area with rattan chairs. At the second level of the Hawaiian home are bedrooms with floors featuring a wooden finish. Meanwhile, high ceilings make these spaces brighter and breezier. It is such a nice place to allow yourself to slacken. Outdoor lounge chairs can be found on the wide green lawn. Take a seat, watch the sunset, and inhale the tropical goodness of Kailua.

Premier Beachfront Getaway

Address: Kailua, Hawaii (see map)

Price: from 1,209 USD / night

Number of Guests: 12

Stayed at this property?

2. Old Hawaii vibes: Spectacular Waimea Oceanfront Estate (from USD 1400)

Sitting on a half-acre (0.2-hectare) private oceanfront property, this vacation home boasts dramatic 180-degree coastline views that look as though they are straight off a postcard. Made of mostly cedar and teak, this house is oozing with distinct Hawaiian charm. It has the makings of the best beach getaway, with the sounds of the waves and the fresh breeze just around the corner. Right from the living room, you will have a view of the coast, even as you watch TV! Meanwhile, what makes the interiors even more distinct are the cathedral ceilings and the cedar finish of the walls. This home’s interior design is indeed a work of art. From the structure itself to the furnishings, there will surely be something to capture your attention. An example is this wooden table, which is placed in the dining area. Spend some me-time in the master bedroom and enjoy the welcome drinks provided by the staff. Every room has its own entertainment system, which includes a flat-screen TV with cable access. For days when you just want to laze around, there’s a terrace with a view where you can hang out. Savor the ambiance because a chance to have a vacation like this don’t come too often in a lifetime!

Stayed at this property?

12.35 km (7.7 mi) from Dole Plantation
112 reviews   Wifi Available
House 8 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
and we loved hanging out on the back patio pool hot tub area
it was perfect for our group of 8 with plenty of room
shrimp trucks were close and ted's bakery was great for breakfast sandwiches and pies
it's clean and well-stocked
he frequently checks to ensure everything is clean and well tended
mike the caretaker was attentive and helpful
the caretaker mike is a sweetheart
mike was super helpful with anything that we needed
all communication with the owner and caretaker was easy and timely
chris is a very nice and responsive property owner
just a really good location
our entire family enjoyed this beautiful house and location
traffic is a challenge other than that owner is great and the location of house is excellent
we hit the toa luau which was also right down the street and was great
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

3. A place to create special memories: Paradise Rental in Diamond Head Kahala (from USD 619)

Renting your own vacation home is the best way to experience Oahu to the fullest. This property, for instance, allows guests to enjoy a secluded space where they can relax, have fun, and even celebrate important life events. This vacation home will give you a world of your own during your well-deserved vacation. Take a refreshing dip in the pool on a warm day and listen to the relaxing sound of a waterfall right in your own backyard. As you enter the home, you will notice paintings and other artworks that are made by local artists. These pieces sure add charm and value to the abode. Aside from the living room, there is a space in the house especially dedicated to families. It is wide and spacious, equipped with an entertainment system for everyone to enjoy. For an adults-only gathering, make use of the bar located adjacent to the living room. It is equipped with special wine glasses and other bar supplies to make your get together an unforgettable one. Plop down and get some rest before you head out again the next day. With the vacation home’s proximity to the beach and cultural attractions, you’ll never run out of things to do!

Stayed at this property?
Honolulu, Hawaii, United States
38.85 km (24.2 mi) from Dole Plantation
PRIVATE VACATION HOME 12 Guests 6 Bedrooms 5 Bathrooms

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

4. A sojourn for the family: Beautiful oasis with pool (from 310 USD / night)

The lively tropical spirit and good-natured people are only a few of the reasons that make Oahu such a nice place to visit. In this vacation home, you will be welcomed the authentic Hawaiian way. Feel at home, but most of all, enjoy the luxuries that you can only experience during a vacation. All of the essentials will be provided, from spices and condiments in the kitchen to the shampoos and lotions in the washrooms. If you’re bringing kids, you can even request a high chair, a baby swing, or a bouncer. There are two twin beds in the master bedroom, which can be combined into a king bed. Meanwhile, other rooms have queen beds. There will be space for everyone in the family, so don’t worry and just breathe in the Hawaiian ambiance. Even the bathrooms are well equipped and spacious. Enjoy your shower time without a fuss and say goodbye to fighting over sink space. Near the pool, you can prepare your Hawaiian-inspired meals on the outdoor barbecue area. Sear pineapples and grill seafood, then enjoy them at the nearby al fresco dining area. Nothing beats a meal shared with the whole family in such a refreshing setting. Take note that once every two weeks, there is a firework show on this side of the town. Take your family to the gardens and watch as the fireworks pop against the sky!

OVC - Beautiful oasis w/pool 1 block from Ocean in Waikiki Beach! – BBB A+

Address: Waikiki Beach, Hawaii

Price: from 310 USD / night

Number of Guests: 6

Stayed at this property?

Oahu, a perfect retreat for beach lovers

Whatever kind of beach activity you like, whether you’re into swimming, snorkeling, or surfing, this island will surely have something for you. Even if you just want to laze around and take photos, Oahu would be an ideal place to visit; especially with the help of these HomeAway and VRBO vacation rentals.

Stayed at this property?
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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Rica is a young freelance worker from the Philippines. She writes for a living, but more importantly, she lives to write. Travel is one of her favorite writing topics, alongside love and...Read more

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