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The Best AirBnB Vacation Rentals In Oahu, 2021

Twenty-five exemplary places to stay in O’ahu.

By The Smoking Chair Editors  |  Sep 27, 2021

If you’re looking for an epic beach vacation in Hawaii, this list of Airbnbs in Oahu is for you. Oahu is one of Hawaii’s main islands and home to the capital, Honolulu. It’s loaded with gorgeous beaches, exciting nightlife, and historic sites like Pearl Harbor and Iolani Palace. If you’re wondering where to stay in Oahu, we’ve gathered up all of the best Airbnbs in Oahu including the most popular spots like Honolulu, North Shore, and Waikiki. Naturally, all of these locations are close to the gorgeous beaches, but some offer even more with resort-style amenities and close proximity to inland hotspots so you’ll never run short on things to do.
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Royal Kailua Estate

$11,500 / night

Royal Kailua Estate

16 guests 8 bedrooms 8 beds 9.5 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

Royal Kailua Estate is a spectacular beachfront villa on Oahu, featuring panoramic ocean views and direct access to Kailua Beach. The palatial, 11,000-square-foot home is ideal for large families or groups of friends, with expansive outdoor living areas, beautifully furnished interiors, and extraordinary amenities for dining, relaxation, and fun. Five bedroom suites in the main house plus a three-bedroom guest house accommodate sixteen guests in total comfort.
The heart of the villa is the central terrace, with a saltwater swimming pool and hot tub set amid gorgeous natural rock. A fabulous dining pavilion is perched amid this lush oasis, featuring a fully equipped kitchen with wet bar and grill. Sun loungers and a cool lanai face the pool, ideal for long hours in the open air. The villa’s ocean-facing side includes additional lounge areas, as well as an ample lawn bordering the beach’s soft white sands. Enchanting lighting—including tiki torches and floodlights in the pool and spa—inspire festive nights under the stars.
The spacious interiors open wide to the pool terrace and ocean, creating dreamy crosscurrents of fresh Pacific air. Multiple salons and lounges offer ample room for cocktail parties or quiet relaxation. The fully equipped kitchen with breakfast bar enjoys ocean views through expansive bay windows, and easily serves the casual dining table and gorgeous formal dining room. There is also a lovely billiard room and a spacious home theater with cinema-style seating and a large screen.
The main house includes five bedroom suites, two of which enjoy furnished lanais and gorgeous ocean views. The master suite boasts a privileged corner position with expansive vistas, and features a walk-in closet, private sitting area, and deluxe bathroom with steam room and jetted tub. The guesthouse includes two king suites and a queen suite, as well as a private living area with dining table and kitchenette. All of the villa’s bedrooms enjoy ensuite bathrooms.
Kailua offers an ideal alternative to the popular resorts and towns on Oahu’s south shore, balancing serenity, natural beauty, and wonderful activities. Beyond your beachfront paradise, you’re within minutes of fabulous watersports activities at Kailua Beach Park, as well as excellent dining and nightlife spots. Honolulu and Waikiki are both within easy driving distance.
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The Sullivan Estate & JK7 SPA Retreat

$10,500 / night

Luxury stay in Haleiwa, Hawaii, United States

10 guests 6 bedrooms 6 beds 5.5 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

This 6-bedroom retreat on Oahu’s North Shore offers an array of high-end spa features—including a JK7 Spa-Sensator, yoga pavilion, sauna and steam room, and massage services—against a backdrop of panoramic Pacific views. The ample pool terrace, oceanfront lounge and dining patio, and extensive lanai invite you to savor organic breakfasts and sunset refreshments, while luminescent interiors exude vintage Hawaiian elegance.

Royal Hawaiian Beach Estate

$10,000 / night

Royal Hawaiian Beach Estate

16 guests 9 bedrooms 10 beds 7.5 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

The Royal Hawaiian Beach Estate is an oceanfront villa located in a prestigious area of Oahu that offers a private resort experience for a family holiday or wedding. Relax and enjoy luxury beach life while surrounded by ocean views right on the sands of top ranked Waimanalo! Renowned as the backdrop for Magnum PI, Lost and Hawaii 5-0, Waimanalo doesn’t allow hotels, making it a perfect getaway from busy tourist spots, while remaining close to many great activities!
The outdoor spaces at this vacation rental offer flexibility for entertaining or relaxing within the private fenced yard and beach entrance. Kick back on the large covered patios, mix drinks at the outdoor bar or fire something up on the barbecue. The large swimming pool features a built-in slide and a lava rock waterfall. You’ll also find an outdoor shower and hot tub! At night the estate is aglow with tiki torches and custom landscape lighting. Enhance any gathering with the indoor/outdoor sound system.
The open floor plan maximizes the breathtaking scenic views via floor-to-ceiling windows and doors which open to the beautiful surroundings. Perks include a beige felt billiard table, foosball, a fitness room with an ocean view, video games, a telescope, a piano and Smart Home technology. Just ten minutes in either direction brings you to shopping and fine restaurants such as Roy’s in Hawaii Kai. Or try locally grown food from Cactus in Kailua.
The main house offers six bedrooms with beautiful ocean views, while the three in the guest house overlook the spectacular Ko’olau Mountains. Open up the guest wing for community living or close it for more privacy. The guest wing can be used as a completely separate three story home with a private entrance, kitchen, dining room and living room. With some additional bedding options, this non-smoking villa accommodates up to twenty guests.
A plethora of water sport options are located in proximity to this villa as well as Sea Life Park where you can swim with the dolphins. You’ll also find Blowhole, Makapu’u Beach and Makapu’u Lighthouse for whale watching just nearby. And don’t forget about the unbelievable trails, such as Koko Crater and Manoa Falls, which make for great adventures!
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Plantation at Paradise Point

$6,150 / night

Secluded beach house that hosted President Obama

10 guests 5 bedrooms 6 beds 5.5 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

Furnished lanais look onto the sea at this secluded Kailua Beach villa that hosted the Obamas during their 2008-2011 winter holidays. Bask in the glow of your own tropical oasis in the cloistered courtyard—a cabana, island spa, and lagoon pool with a waterfall are sheltered by lush vegetation. Stained glass, African carvings, and snorkeling gear add charm, and you’re 5 minutes away from tennis and golf.

Espacio Waikiki Penthouse

$5,300 / night

Luxury stay in Honolulu, Hawaii, United States

6 guests 2 bedrooms 2 beds 2.5 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

The oceanfront Kalakaua Villa offers a prime location near Waikiki Beach on Oahu’s South Shore, about a mile from Diamond Head Lookout and the coveted breakers of Tongs Beach. An open-concept interior with fully equipped kitchen and surf-inspired décor opens to a patio poised above waves, while a rooftop terrace enjoys a privileged panorama of the volcano and ocean. Four bedrooms include a master suite with private balcony and Jacuzzi tub.

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Kaikuono Villa

$4,238 / night

Contemporary villa near Diamond Head Crater

8 guests 4 bedrooms 5 beds 4.5 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

An upper-level great room with Buddhist-inspired décor opens to a lanai over towering palms and modernist sculptures at this waterfront villa in Kahala. Less than a mile from Diamond Head Crater, you get views of ocean and volcano, and a winding staircase leads to Zen-like bedrooms with private balconies. Waikiki is 3 miles up the beach, so pick your water sport, or golf course, and dive in.

Kahala Oceanside

$3,493 / night

Luxury stay in Honolulu, Hawaii, United States

14 guests 6 bedrooms 6 beds 6.5 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

This spectacular oceanfront villa on Oahu is situated within walking distance of Kahala Beach, about a mile from Diamond Head Lookout, with expansive views of the Pacific Ocean. The gated property offers exquisite privacy and high-end amenities for relaxation and entertainment, including a lagoon-style swimming pool and hot tub, outdoor entertainment area, and gourmet kitchen. The villa comprises a main house with two master suites, along with four deluxe private cottages arranged around a lush garden sanctuary—accommodating up to fourteen guests. A wide array of deluxe services and activities are available.
The home is nestled amid lush tropical trees yielding to expansive ocean vistas, evoking an ambiance of seaside oasis. Generous outdoor living areas on both levels invite you to long days and evenings in the open air. Soak your body in the stone-framed hot tub and plunge into the refreshing pool. Sunbathe on elegant lounge chairs on the upper balcony, or relax in the cool shade of the lower veranda. Kindle the barbecue in the afternoon and relish alfresco meals in the dreamy breeze.
The main house opens directly to the veranda as well as the interior gardens, creating a lovely crosscurrent of ocean air. The cavernous living room features double-height ceilings and comfortable sofas, with a wide threshold leading into the beautiful dining room. Pocket doors fuse the indoor and outdoor dining areas, forming an ample venue for dinner parties. Multiple dens offer quiet retreats for afternoon downtime or late-night fun.
The main house includes two ocean-view master suites, each with a king bed, walk-in closet, sound system, and ensuite bathroom (one of which includes a lovely tub). The Kahala Master opens directly to a private furnished balcony, while the Waikiki Master has its own interior living room. Each of the four garden cottages is essentially a master suite, with king bed, walk-in closet, and ensuite bathroom. The Maui Cottage includes a kitchenette, while the Hawaii Cottage has its own fully equipped kitchen and a queen-size sofa bed.
The villa is just steps from Kahala Beach and about a mile from Wai’alae Beach. Kahala Mall is less than two miles away, and you’re within easy reach of Waikiki, Honolulu Zoo, Ala Wai Golf Course, and much more.
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Kalakaua Villa

$2,276 / night

Kalakaua Villa – 4Br – Sleeps 8

8 guests 4 bedrooms 4 beds 4.5 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

The oceanfront Kalakaua Villa offers a prime location near Waikiki Beach on Oahu’s South Shore, about a mile from Diamond Head Lookout and the coveted breakers of Tongs Beach. An open-concept interior with fully equipped kitchen and surf-inspired décor opens to a patio poised above waves, while a rooftop terrace enjoys a privileged panorama of the volcano and ocean. Four bedrooms include a master suite with private balcony and Jacuzzi tub.

Lani Loa

$2,100 / night

Entire residential home hosted by Christopher And Elizabeth

14 guests 6 bedrooms 8 beds 4.5 baths

The house was huge and in the perfect location for our trip. If you want an ocean view you could not get anything better. The only way to be closer to the water is to be in the water. Do not expect to access the water from the house, you can’t. The beach you can access is a very short 2 minute walk up and across the street from the driveway. There is a private access path between two of the homes. Do not make the mistake I did and wait to go and check out that beach. It is perfect and private. You do not need to look for anything better. The list of things you can do within a half hours drive is endless. Kualoa Ranch (Jurassic Park), The Polynesian Cultural Center, Zip-line Tours, Turtle Bay, Helicopter Rides and pretty much anything else you want to do. Groceries are 5 minutes away. I say forget the groceries and go to the food trucks. If you like local foods, the food trucks are a must. They are about 15 minutes further north on the highway. Go, stay and enjoy this great ABNB property. Aloha!!!

— Review by Troy

Experience Oceanfront Paradise on O’ahu

$2,015 / night

Entire villa hosted by Jon

16 guests 6 bedrooms 11 beds 6.5 baths

The house was everything we wanted it to be and more. Jon and Mary were very gracious hosts with great communication and attentiveness to any needs. The house is stocked with everything you could possibly want, including tons of ocean-related accessories. They even had an entire bucket of water shoes, extra hats, beach chairs, anything you could imagine needing for a day at the beach anywhere on the island. We had a lot of fun kayaking and paddleboarding right from the backyard, and we even saw sea turtles out there. The house was very spacious and well appointed. We very comfortably fit two families and could easily have comfortably fit a third family. The location is great for various activities, including nearby jet-skiing, snorkeling at beautiful Hanauma Bay, a stunning drive up the Eastern coast of Oahu, a day at Waikiki Beach, zip lining at Kualoa Ranch, and many more activities. We hope to return someday soon.

— Review by Nadia

Maluhia ~ Peace & Tranquility

$1,800 / night

Entire residential home hosted by Donna

10 guests 4 bedrooms 6 beds 4.5 baths

Speechless is what this place will leave you. The house is in a quiet part of the north shore, totally inconspicuous. But once you pull in and walk to the back or upstairs the lanai, you will be blown away. The home was everything we needed and more for an incredible family trip after not having seen our families in almost a year. Donna was an incredible host, giving us complete privacy but also allowing herself to be available should we have needed anything. Which we didn’t, because The house was so well equipped. This trip will be one we talk about for years to come! And we hope to come back in the future.

— Review by Evita

Seaside Hideaway

$1,790 / night

Contemporary Bungalow on the Pacific

6 guests 3 bedrooms  beds 2 baths

Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

This 3-bedroom villa is perched between Diamond Head Lookout and Doris Duke’s famed Shangri La Estate. An upper lanai with alfresco dining overlooks a lower terrace, where a pool and hot tub are cradled within rocks and gardens like tropical lagoons. Expansive ocean views pervade the home, while the design fuses Buddhist artwork and rustic cottage accents with high-end amenities for cooking, fitness, and entertainment.

Sea of Glass – Luxury North Shore BEACHFRONT home

$1,743 / night

Entire residential home hosted by Priscilla

8 guests 4 bedrooms 5 beds 4.5 baths

This home is truly like living in paradise with a spectacular view of the ocean from the inside and out. The furnishings and amenities inside made this home a place where you could relax, enjoy, and totally unwind. The ocean immediately outside the large expanse of yard, provided a magical world of mesmerizing waves which were beautiful, mysterious, and wild. Priscilla, the owner, was very responsive and the home was immaculate and roomy with many smart home features which made it easy to operate. Two masters faced the ocean and had access to the balcony with clear railings which brought the ocean view into the bedrooms and living space. One master faced the incredible mountains and a 4th bedroom had direct access to a hall bathroom and had 2 single beds and a loft bed. The expansive open floor plan for the living area was well planned out and allowed for people to gather around the large waterfall island, long dining table, extremely comfortable L-shaped sofa facing a huge flat screened TV, or game table loaded with fun activities. Downstairs access to the lawn had the ability to close off the inside with sliding glass doors to keep winds out while enjoying the view on sofas and chairs. The outside back yard had various hanging, reclining, and large cocoon chairs along with an outdoor shower and grill. This home caters to your every desire.

— Review by Roseanne

A View to Die for! 3bedroom 3bath on Waikiki Beach

$1,390 / night

Entire condominium (condo) hosted by Tommy

8 guests 3 bedrooms 6 beds 3 baths

When it says a view to die for, it’s a view to die for! It was like staying in your own beach vacation condo because it was a home, not a hotel. You just need to buy the food you’re gonna cook. All dishes are provided (pots, pans, plates, utensils, etc.) and if you don’t want to cook, there’s a lot of places to eat. My twin boys (17 years old and Seniors in high school) decided to bring their PS4 because it would be for playing at night. Kids now a days are attached to electronics but this place had them actually looking at the beach from the room with provided binoculars, amazed by how close the turtles swim up to the wall. That made them decide to venture to the beach just downstairs….literally less than 25 steps from the elevator (but who’s counting!) They even walked through Waikiki after dinner. Seeing how much they enjoyed themselves…priceless. Anything that makes my kids happy makes Mommy happy! Ok, about the condo, it looks exactly like the listing! Once you walk in, to the left is the kitchen and past that are 2 queen size sofa beds. There are dividing doors that can separate the room from the kitchen making it 1 bedroom. In the living room is another sofa bed and in front of that are 2 twin beds that can also be separated from living room with dividers. The master bedroom has a king size bed and a full bathroom with a stand up shower. The 2nd full bathroom has a shower and tub and the washer and dryer. The 3rd full bathroom has his/hers sink and a shower with tub. So happy for this because there were 5 high school boys with me and I had my own bathroom! Also provided are beach chairs, beach umbrella, snorkels, detergent for laundry, and toiletries. Ok now the host, Tommy was awesome at communicating with me. I can text him, call him or send a message through AirBNB. He responds right away. When I checked out 6am on Monday and called him because I had a question, it wasn’t too early for him to be available. We actually had conversations about other stuff not just about the condo. He was humble and sincere when we spoke. I don’t ever want to just stay at a boring hotel anymore, not worth it. This is a long review but believe me when I say there are not enough words that would come close to explaining what we’ve experienced here! Thank you Tommy and I hope that I can stay again in the future. It’s all booked up!

— Review by Janice Olga

Breathtaking Ocean Views, Pool & Hot Tub

$1,250 / night

Entire residential home hosted by Wailele

8 guests 4 bedrooms 4 beds 3.5 baths

WOW!!! Five Stars and then some. Checkin was super easy, when you first open the front door, your jaw drops when you see the massive indoor waterfall and beautiful layout.
The place was breathtaking and immaculately clean. Wailele thought of EVERYTHING, and there is a Big thorough manual that provides detailed instructions on anything and everything you’ll need to know.
A spectacular host and a blessing to work with.
This is a house that will not disappoint in ANY possible way and an experience that will last a lifetime!

— Review by Joshua

Breezy Island Living in Private Beachfront Getaway

$1,022 / night

Entire residential home hosted by Tracy

8 guests 4 bedrooms 6 beds 2 bath

We stayed here for a month in Jan/Feb 2021. The property is spectacular, absolutely gorgeous and we thought it was the perfect place to be on Oahu. No matter where you stay on the island, it is about an hour’s drive to go anywhere else, and that is the case here. That being said, there are lots of wonderful hikes and beaches on the Westside that are very short drives from the house.

The house itself was lovely, I think it looks nicer than the pictures show. We had five people (four adults and one kid) and the set up was perfect for us. My husband is in a wheelchair and he did fine at the property with some ramps that we brought ourselves and taking outdoor showers.

Can’t wait to go back!

— Review by Kristine

Bird Of Paradise TVU-1868 – Ke Iki Beach Bungalows

$795 / night

Entire bungalow hosted by Greg

5 guests 2 bedrooms 2 beds 1 bath

This is the best location in the North Shore. We visited in summer and loved the true beachfront location that allowed us to enjoy the flat, warm water, perfect for swimming or floating. The accommodations were clean, charming and right on the beach. There are hammocks, beach chairs, umbrellas, beach towels and anything else you could think of. The kitchen was well equipped and even had spices and oils. Shampoo and conditioner was quality and ample quantities. The staff is kind and helpful. I can see why families come back year after year. We will definitely be back ourselves!

— Review by Kelly

Sandy Beachfront Home

$766 / night

Entire residential home hosted by Shawn

8 guests 3 bedrooms 4 beds 3 bath

This house is amazing!!! Great location, great views, so much gear to use to play in the water… It was so relaxing and I was pleasantly surprised with all the sleeping options. It is so beautifully decorated with such fun art all over the house to look at. Our favorite thing to do was to sit on the deck and watch the ocean and beautiful sunrises. Our stay was perfect and there is nothing I can think of that could have made it better! Thank you for renting your beautiful home to us!!!

— Review by Laura

The Hibiscus TVU-1869 – ke Iki Beach Bungalows

$752 / night

Entire bungalow hosted by Greg

5 guests 2 bedrooms 2 beds 1 bath

Set in front of the most beautiful beach in Oahu, Ke Iki Bungalows is the perfect getaway to enjoy time with your friends and loved ones. The space provides one of the best spots to view sunset, swim, or just enjoy sunbathing on Oahu’s North Shore. The bungalows are nicely renovated with everything you need to make your stay comfortable. The caretaker and the owner are so nice too! We highly recommend their place and we will certainly come back to this special place! Much mahalo, salamat, and kiitos from Juha and Andrea 🙂

— Review by Andrea Christina

Haleiwa/North Shore! Entire OCEANFRONT HOME

$725 / night

Entire residential home hosted by Moniza

8 guests 3 bedrooms 4 beds 2 baths

Moniza’s house is one of the best ohana-style accommodations we have ever stayed in! The location is stunning and you are able to fully appreciate it from the upstairs deck. The beach was ideal for relaxing days by the water since it is just a little ways away from the crowded Sunset Beach Park which keeps most of the crowds away. The house itself had every possible amenity you could want (including a crucial ice maker) and we were constantly surprised by the “little things” around the house that made it feel like home. Comfortable and functional furniture that gave us plenty of space for lounging/sleeping and overall the space was roomier than anticipated. I would 100% recommend this home to anybody looking for a group vacation home on the North Shore! We will be back!

— Review by Lawrence

Sunset Villa

$640 / night

Entire residential home hosted by Jessica

6 guests 3 bedroom 4 bed 2 baths

This is a wonderfully appointed house within easy walking distance of the beach. What you see in the pics does justice to the comfort and amenities the house has to offer.

The house is well equipped, comfortable and a perfect base for a holiday on the N. Shore.

Ted’s is great for breakfast. Banzai Bowl too is an easy walk. Indeed, you can use the path to walk along the shore front and hit several beaches including Sharks Cove.

❤️TheNShore!

We’ve had a glorious week and are deeply grateful to Jessica for hosting us.

— Review by Rupert

Moeʻuhane Kai Beach Front Home

$639 / night

Entire residential home hosted by Kristen

8 guests 4 bedroom 5 bed 2.5 baths

This was the most amazing air bnb I’ve ever been to! Not only was the house so beautiful and clean, it had EVERY THING you could possibly need. The view from inside was STUNNING!! You literally wake up to the ocean and a beautiful sunrise. Everything about this home was just PERFECT!

Kristin was the best host I’ve ever had. She was so quick at responses and very kind and helpful. She definitely made our stay memorable!! So thankful we had Kristin as our host. I would for sure come back to this house every chance I get. It is totally worth every penny!!

— Review by Manu

Sea Cliff House – Oceanfront – 30 Day Stays

$602 / night

Entire townhouse hosted by Geoff

10 guests 3 bedroom 7 bed 2 baths

What a magical place!! Views for days! The best sunrises for your morning coffee. Now that we’re back home it’s way too quiet and we miss the endless sound of the sea. The house came with all the convenient necessities for our stay especially the beach gear. Perfect location to get anywhere on the island and we loved how the house was on the beautiful peninsula. The aloha spirit is contagious! Loved Geoffs spot!

— Review by McKenzie

North Shore Surf House

$600 / night

Entire residential home hosted by Daniel & Bryn

3 guests 1 bedroom 1 bed 1.5 baths

The North Shore Beach House is an amazing find, with some of the North Shore’s most pristine beaches just steps away. You can see and hear the beach from every room (except the bathroom) in the house and it has a well kept grass area where you can relax. You really can’t beat it!

— Review by Michelle

PARADISE FOUND! BEACHFRONT TROPICAL OCEAN OASIS

$563 / night

Entire residential home hosted by Karen

9 guests 3 bedroom 6 bed 3 baths

This is a wonderful location for those who want to be super close to a wonderful swimming beach with a few fun waves. We loved swimming, boogie boarding, SUP’ing and even surfing at Makaha beach. The walk to the beach from the house was enjoyable and easy. We loved the vibe at Waianae, locals, families and a few tourists all hanging out peacefully together. We were 40 minutes to Costco and the airport and we drove all over the Island. Honolulu, Lanikai, North Shore for surf lessons and Hanauma bay for snorkeling. The house was perfect for our multi generational family reunion. It slept 8 comfortably with room for a few more on the comfy couches in the living room. The kitchen was delightful. I cooked while enjoying the ocean view or getting to watch whatever movie the kids chose that night. We had a wonderful time at this house and we’d book it again in a heart beat. Our kids loved it, our grandparents loved it and we loved it too!

— Review by Erin

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