Airbnb Kailua, Oahu Vacation Homes, Beach Houses, Apartments, & Short-Term Rentals

Kailua Airbnbs: 12 Perfect Hawaiian Vacation Homes

Once upon a time, Kailua was just a sleepy, quaint town on the east side of Oahu. But over the past decade, this town has bloomed into a lively town filled with healthy restaurants, local art galleries, lovely boutique shops, and beautiful beaches.

Now visitors flock to Kailua to hike the Olomana Trail, try vegan lau lau (a traditional Hawaiian dish made from fish or pork steamed in ti leaves) from Ai Love Nalo, and enjoy the calm waters and powdery white sand of Lanikai Beach. As an Oahu local, I head to Kailua quite often. I just can’t resist the breathtaking beaches, exciting hikes, and delicious eateries.

Kailua is packed with amazing vacation rentals. You can stay in a quaint little studio, a Hawaiian-style cottage, or a beachfront mansion – whichever matches your vacation vibe! With all of these fantastic options, you might find it hard to choose just one place to stay. So to help, I’ve compiled a list of 12 of the best Airbnbs in Kailua to make planning your Hawaiian holiday a breeze. Enjoy!

Note: If you’re still deciding where to stay on the island make sure you check out our article, Where to Stay on Oahu.

Top 10 Things To Do in Kailua

Kailua Airbnbs, Vacation Homes, Beach Houses, Apartments & Short-Term Rentals
  1. Spend a day enjoying the warm sunshine, brilliant blue waters, and sparkling sand of Kailua Beach. This beach is so beautiful that it is consistently ranked as one of the best beaches in the world.
  2. Visit the neighboring beach of Lanikai Beach. With the same turquoise waters and pristine sand, Lanikai Beach is the slightly more secluded counterpart of Kailua Beach.
  3. Kayak to the Mokulua Islands, commonly known as “The Mokes”. As the most popular kayaking adventure on the island, the trip to the picturesque mokes is definitely a must-do during your time in Kailua.
  4. Hike the Lanikai Pillbox trail for sunrise. Sit on the abandoned bunker while watching the sun come up behind the Mokulua Islands.
  5. See an ancient Hawaiian temple, or heiau, at the Ulupo Heiau State Historic Site. Once upon a time, the ancient Hawaiians prayed at the Ulupo Heiau for protection and good fishing conditions.
  6. Tackle the three peaks of the Olomana Trail. This hike is quite a challenge, but you’ll be rewarded with amazing views throughout the trail. But remember to stay safe, as this is one of the most dangerous hikes on the island!
  7. Purchase a few tasty goodies at the Kailua Farmers Market. Exotic fresh fruits, guava-smoked barbecue, spam musubis, and the famous apple banana ice cream from the Cold Fyyre booth are a few you must try!
  8. Stop and smell the flowers at Lyon Arboretum. This attraction is home to hundreds of beautiful plants and even a small waterfall.
  9. Hike to the 25-foot Maunawili Falls. If you’re lucky, it might be passion fruit (lilikoi) season, and you’ll be able to pick some tangy fruits right off the tree!
  10. Dine on locally caught fresh fish at Nico’s Kailua. Try the furikake pan-seared ahi, fish and chips, or even a well-seasoned poke bowl.
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Why Stay in an Airbnb in Kailua

Why Stay in an Airbnb in Kailua, Oahu, Hawaii

There are no hotels in Kailua, so your only option is to stay at a vacation rental. But luckily there are plenty of cool Airbnbs in Kailua, so you can find one that perfectly suits your budget and style of travel!

Airbnbs also have the coolest amenities. From private pools to private gardens to all the beach gear you could dream of, you’ll get to enjoy many extras that you wouldn’t get to experience at a regular hotel or resort.

Finally, one of the greatest perks of staying in an Airbnb in Kailua is the fact that you can connect with a local before you even land on the island. Airbnb hosts are typically quite friendly and love to share local tips. You can find out about hidden beaches, secret hikes, adorable shops, and fantastic restaurants in Kailua.

Search Kailua Hotels and Vacation Rentals


The 12 Best Airbnbs in Kailua

Best Kailua Airbnbs for Couples and Solo Travelers

1. Luxurious Kailua Beach Apartment

Best Airbnbs in Kailua, Oahu: Luxury Beach Apartment
Images courtesy of Airbnb

With rave reviews, an inviting atmosphere, and breathtaking ocean views, this luxurious beach apartment is definitely one of the best Airbnbs in Kailua!

As you walk through the front door of this welcoming home, you’ll immediately notice the natural light streaming through the sheer curtains, the pristine white furniture, and the eye-catching turquoise touches in the living room and kitchen area. As you venture into the bedroom, these inviting aspects continue from the plush queen mattress to the aquamarine candles.

And outside is a lovely balcony with a dining table for two where you can spend hours simply enjoying the calming environment and beautiful ocean views.

Situated midway between Kailua Beach and Lanikai Beach, this cozy apartment will give you easy access to both of these gorgeous beaches.


2. The Tiki Room: Kailua Beach Studio

Best Kailua Airbnbs & Vacation Rentals: Tiki Room
Images courtesy of The Tiki Room

The Tiki Room is definitely one of the most unique Kailua Airbnbs! Once upon a time, traveling Polynesians introduced tikis to the native Hawaiian people. The Hawaiians then followed the Polynesians’ example and began to create wooden carvings of Hawaiian gods, also known as tikis. This amazing condo embraces tiki-related decor, including intricate tiki wall art and colorful tiki mugs.

In addition to the fantastic theming, this home includes one plush king bed covered in colorful pillows, a small dining area, and a stocked kitchenette. You’ll also have access to all the beach gear you could want, including beach chairs, boogie boards, snorkel gear, an umbrella, and a cooler.

As for the location, the Tiki Room is just steps from Kailua Beach! You can spend all day on the sandy shores before returning home to fall asleep to the sound of the ocean waves crashing against the shore.

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3. Bright & Welcoming Kailua Pineapple Studio

Best Airbnbs Kailua Beach: Pineapple Studio
Images courtesy of Airbnb

In addition to the fun tiki-themed condo, Kailua is also home to a pineapple-themed studio. With bright welcoming yellow walls, you’ll certainly never forget the inspiration for the Kailua Pineapple Studio.

This adorable vacation rental is a single large living space that features a comfortable king bed, a bird of paradise-bedecked couch, a newly-remodeled kitchen, and a glass dining table for two. Plus you’ll have beach towels, beach chairs, and a beach umbrella available for your use.

The Kailua Pineapple Studio is about midway between Kailua Beach and Kailua town. So while you can certainly enjoy the world-renowned beach, you can also grab an acai bowl from Lanikai Juice, stop by the Kailua Farmers Market, and peruse the nearby art galleries.


4. Secluded Kailua Beach Bungalow

Best Kailua Airbnbs & Vacation Rentals: Beach Bungalow
Images courtesy of Airbnb

This secluded Kailua beach bungalow may be one of the coolest Airbnbs in Kailua, thanks to its tranquil private garden.

While Airbnbs often offer unique amenities, private gardens are quite rare – and the garden at this Kailua home is exquisite. With over 300 plant species, a trickling fountain, traditional sculptures from all around the world, and colorful macaws that like to visit every now and then, you’ll need to dedicate some time to enjoy the property’s lush greenery.

And all this beauty is outside of the house – just wait until you see the inside! You’ll find one plush queen bed with a unique bamboo headboard, a well-appointed kitchen with views of the garden, and a living room showcasing pieces from local artists.

As with many of the best Kailua Airbnbs, this beach bungalow is just a short walk from Kailua Beach.


Best Kailua Airbnbs for Small Groups and Families

5. Hale Nanea: Cozy 3-Bedroom Beach House

Cool Airbnbs in Kailua, Oahu: Hale Nanea
Images courtesy of Airbnb

Thanks to its unique interior design and prime location, Hale Nanea is one of the top-rated Airbnbs in Kailua. Hale Nanea, which means “House of Relaxation,” truly lives up to its name. With a zen garden filled with bonsai trees, a calming outdoor patio, and a spacious living room area, you’ll certainly feel relaxed here.

This vacation rental also includes three plush queen beds, a small dining area, and loads of beach gear for you to borrow. You won’t have to worry about a thing while staying at this well-appointed Kailua Airbnb.

It takes less than five minutes to walk to Kailua Beach from Hale Nanea, so you really can’t ask for a better location. And you’ll also be able to make the short drive into Kailua town, where you can grab a tasty breakfast from Morning Brew, wander around the Lauren Roth Art gallery, and try kalua pig from Kono’s.

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6. The Lake House on Ka‘elepulu Pond

Best Kailua Beach Airbnbs & Vacation Rentals: The Lake House
Images courtesy of Airbnb

When most people think of Kailua, they think of the beach – and for good reason. But the vast majority of people, Hawaii locals included, don’t realize that Kailua is also home to a couple of beautiful lakes and ponds.

The Lake House is situated in the Kailua Enchanted Lakes neighborhood on the shores of Ka‘elepulu Pond. And thanks to the sliding glass doors, the outdoor patio with a fire pit, and the lakeside saltwater pool, you can enjoy the beauty of Ka‘elepulu Pond as often as you would like.

This wonderful house includes two cozy bedrooms filled with natural light, a large kitchen with granite countertops, a comfortable seating area with a 65” flatscreen TV, and a dining area for eight. As an added bonus, The Lake House offers awesome amenities, including two brightly colored bikes, a two-person kayak, and even a handful of life vests.

As for the location, The Lake House is in the residential area of Kailua so you’ll be close to quite a few cool spots including Maui Mike’s Fire-Roasted Chicken and the Lanikai Pillbox Hike.


7. Hawaiian-Style Ocean View Cottage

This Hawaiian-style ocean view cottage is certainly one of the best Airbnbs in Kailua! Not only will you experience Hawaii life and culture while you’re out and about, but you’ll also be able to get a taste of it while you’re staying in this home as well.

With the woven bamboo touches, wooden ceiling fan, and monstera leaf-patterned fabrics, there’s no doubt that this is a Hawaiian-style home. These classic Hawaiian features weave their way throughout the two comfortable bedrooms, the well-equipped kitchenette, and the welcoming seating area as well.

And let’s not forget about the private yard, where you can spend even more time in the sunshine!

One of the biggest perks of this ocean view Airbnb is the location. You’ll be just a short walk away from both Lanikai Beach and the start of the Lanikai Pillbox Trail.

Check Price & Availability on VRBO


Best Kailua Airbnbs for Large Groups and Events

8. Stately Beachfront Mansion that Hosted President Obama

Best Kailua Airbnbs & Vacation Rentals: Plantation at Paradise Point
Images courtesy of Plantation Estate

Between the pineapple-inspired studio and the tiki-themed apartment, there are certainly quite a few unique Airbnbs in Kailua. But there are none quite as special as this expansive Kailua Beach House that hosted President Barack Obama every single winter from 2008 to 2011!

The interior of this mansion is a wonderful combination of modern design with Hawaiian-inspired touches. You’ll enter through a gorgeous carved wooden door into the large seating area with earthy green accent walls and lots of natural light. From there, you can wander into the dozens of other jaw-dropping rooms in this luxurious villa, including the five nature-inspired bedrooms, the stylish dining room, and the comfy common space.

And just wait until you see the backyard! You’ll absolutely love lounging in the secluded cabana and swimming in the lagoon-like pool with cascading waterfall, all while surrounded by lush greenery. With all of these amazing features, it’s clearly worthy of a president.

As can be expected, the location of this extravagant mansion is also fantastic. Situated on the shores of the most secluded part of Kailua Beach, you can easily spend all day floating in the calm turquoise waters. You can also kayak in Kaneohe Bay and dine on fresh fish at Nico’s Kailua.

Check Price & Availability on VRBO

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9. Walker’s Lanikai Beach House

The lavish mansion that hosted President Obama isn’t the only spectacular Airbnb in Kailua. Walker’s Lanikai Beach House is situated on the shores of the stunning Lanikai Beach, and thanks to the huge glass windows in practically every single room, you can enjoy views of the gorgeous Pacific Ocean all the time.

And the ocean theme continues into the interior of the house through blue pops of color and beach-inspired signs. You’ll love gazing out at the idyllic beach whether you’re waking up in one of the five cozy bedrooms, cooking in the well-appointed kitchen, dining in the beautiful dining area, or sunbathing on the outdoor deck.

While staying at Walker’s Lanikai Beach House, you’ll want to take advantage of its prime location right on Lanikai Beach. Soak in your daily dose of Vitamin D under the warm sun, swim around the calm aquamarine waters, and rent a kayak to visit the Mokulua Islands.

Check Price & Availability on VRBO


10. Royal Kailua Estate: Luxurious 8-Bedroom Villa

Best Kailua Airbnbs & Vacation Rentals: Royal Kailua Estate
Images courtesy of Airbnb

With a saltwater swimming pool, tiki torches, a pool table, and a movie room, the Royal Kailua Estate is certainly one of the coolest Airbnbs in Kailua!

The second you walk through the lava rock gate and onto the property, you’ll feel like a millionaire. As you make your way inside the home, you’ll be in awe of the luxurious kitchen, the Hawaiian-inspired living room, the flower-accented dining room, and the eight magnificent bedrooms.

And that’s just what’s inside of this sprawling Royal Kailua Estate. Once you take a peek at the backyard, you’ll never want to leave this mansion! Spend the afternoon swimming in that lagoon-style swimming pool or lounging in the lavish pool cabana complete with gourmet kitchen and bar. Regardless of your preference, you can easily spend hours enjoying all of the perks of this amazing Kailua Airbnb.

And to top it all off, the Royal Kailua Beach Estate is just a few steps away from the famous Kailua Beach. It’s truly hard to beat this incredible vacation home!

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11. Lanikai Ocean View Villa: The Best Views in Kailua!

Best Airbnbs in Kailua, Oahu: Lanikai Ocean View Villa
Images courtesy of Airbnb

Kailua is filled with extravagant homes, and the Lanikai Ocean View Villa just adds to the town’s collection.

This lavish villa combines a sense of luxury with whimsical accents. As you make your way through the estate, you’ll notice island-inspired pineapple light fixtures, sparkling glass walls, and intricate wooden turtle carvings. These lovely touches weave their way through the four beach-inspired bedrooms, the eye-catching dining room with a view of the mokes, the well-appointed kitchen with luxury appliances, and the comfortable living room.

And while the interior of the home deserves a feature in Architectural Digest, you may find yourself spending all of your time outdoors. Swim in the brilliant blue pool, kick around a soccer ball in the grassy backyard, or sip a coffee on the sunny balcony while staring out at the breathtaking view.

This lovely villa is within walking distance of the stunning Lanikai Beach and the beautiful Lanikai Pillbox Hike.


12. Kehaulani Villa: Stylish Kailua Vacation Home for 10

Best Kailua Airbnbs & Vacation Rentals: Kehaulani Luxury Villa
Images courtesy of Kehaulani Villa

The Kehaulani Villa actually consists of two homes – the main house and a guest house. Both of these homes offer unparalleled views of the picturesque Mokulua Islands and the deep blue Pacific Ocean.

And while the views are certainly the highlight, the two homes on the property aren’t too shabby either. As a matter of fact, this estate was designed by a locally renowned interior designer. And between the etched glass barriers, beautiful floral wall art, and teal touches, you can certainly tell!

The villa includes four lavish bedrooms with private balconies, an inviting living room with a rustic coffee table, and a dining room blessed with an abundance of natural light. As an added bonus, the property also includes a small private garden with lush plants and trickling waterfall.

The Kehaulani is conveniently situated midway between Lanikai Beach and Bellows Beach.

Check Price & Availability on vrbo

That’s it – 12 of the best Airbnbs in Kailua! Do you have a favorite vacation rental in Kailua? Let us know in the comments below.


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Sarah Etinas - Bio Photo

Sarah Etinas – About the Author:

Sarah is a travel writer based on the beautiful island of Oahu, Hawaii. When she’s not enjoying the stunning beaches and hikes of her home island, she’s going on exciting adventures all around the world. A few of her most thrilling adventures have included snowshoeing in the Swiss Alps, kayaking through a river of jellyfish in the Caribbean, and sleeping in a sandstorm in the Sahara Desert.

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