Oahu Vacation Rentals – Explore Condos, Villas & Beachfront Homes

Oahu vacation rentals range from oceanfront condos in Waikiki to luxurious resorts in Ko Olina, surfside escapes on the North Shore, and peaceful retreats in towns like Kailua and Waialua. With options for families, couples, long-term visitors, and remote workers, Oahu offers the perfect stay for every traveler.

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Gorgeous Condo w/ Ocean View, Near Beach + Parking

Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Waikiki Shore 1302

Waikiki Shore #1302 – 2161 Kalia Rd.(ALL ONLINE RESERVATIONS CONSIDERED REQUESTS SUBJECT TO APPROVAL.)You'll enjoy spectacular ocean and Diamond Head views from both sides of this luxurious 2-bedroom, 2-bath condo on one of the uppermost, ocean-facing floors of the...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

Majestic Mahakea – Oceanfront Oasis on Oahu's North Shore

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Majestic Mahakea: Oceanfront Oasis...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Laie, Hawaii

New! Sans Souci 1004 1B/1B/1P Stunning unit w/ Ocean front view

Sans Souci, located on the southeastern coast of Oahu, Hawaii, is a captivating coastal paradise on Kaimana Beach, near Colony surf condominium, Zoo, Waikiki Beach. Enjoy pristine sandy shores, crystal-clear waters, and lush greenery for sunbathing, swimming, and...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

North Shore Condo Rental at Kuilima

Relax to swaying palms, stunning seas and a tropical breeze! You deserve it! Step right out the lanai onto fairway one of the Fazio golf course. Swaying Palms is an end unit, situated within the complex to provide lots of natural light, privacy, and a more spacious...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kahuku, Hawaii

Luxurious Golf Course Ko Olina Kai Estates Getaway w/Parking & Near the Beach

This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.This property is located at 92-1043 Koio Drive.This enchanting second floor home away from home is situated...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kapolei, Hawaii

Luxury home on a 2-acre gated estate in Central Oahu

Escape to a secured and quiet environment after a day of fun and madness. Just 33 minutes to Waikiki * 30 minutes to the North Shore, this newly renovated executive home has split AC & heat in every room * fitness gym * large covered patio for BBQ * modern kitchen *...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Wahiawa, Hawaii

Waimanalo Beach Cottages – Tranquil Island Retreat Steps from the Shore

Uncover the allure of Waimanalo and lose yourself in the tropical paradise of Waimanalo Beach, where our exquisite cottages and breathtaking surroundings await. Embark on a journey of discovery by indulging in the myriad of exciting activities we have to offer....

🛏 9 Bedrooms
🛁 9 Bathrooms
👤 Sleeps 24
📍 Waimanalo, Hawaii

Available and legal for stays less than 30 days.

Hawaii Sheffield House has been a legal bed and breakfast for over 35 years. We are available and legal for stays of less than 30 days. We provide a unique neighborhood stay in Kailua Hawaii that is just down the street from Kailua Beach.The Hawaii Sheffield House...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii

Kahala Beachfront Estate – Private Resort-Style Living

For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10- 12 Night Minimum over the Christmas/New Years Holiday Season at $8,400 per night.Spacious beachfront estate is situated on lush tropical grounds,...

🛏 7 Bedrooms
🛁 7 Bathrooms
👤 Sleeps 14
📍 Honolulu, Hawaii

Two-story ocean view home with a furnished patio & deck, washer/dryer, & AC

Ka Hale me Ka ike 30 Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in the amazing view from both inside and out at this four-bedroom, family-friendly retreat here...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kaneohe, Hawaii

Makaha-465 Farrington: Spacious 4BR Oceanfront Haven with Modern Amenities

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Escape to the enchanting shores of Oahu at...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Waianae, Hawaii

Create unforgettable memories in this Modern Family Friendly Villa in KoOlina!!

Choose to spend your days on the Ko Olina Championship golf course or at the Marina; relax at one of four breathtaking sandy lagoons, pamper yourself at the award winning Four Seasons Resort and Spa; spoil the kids at Au’lani Disney Resort or explore the rich culture...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Kapolei, Hawaii

Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise

Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, deciding whether to go to...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Honolulu, Hawaii

Epic Forest View, A/C, Fruit Trees, Beach 5m drive

Experience this forest retreat complete with a cozy queen bed, AIR CONDITIONING, vaulted ceilings, convenient kitchenette, half bath, and an outdoor hot/cold shower. Relax on the expansive deck facing breathtaking panoramic views of the untouched jungle. Immerse...

🛏 1 Bedroom
🛁 0 Bathrooms
👤 Sleeps 2
📍 Haleiwa, Hawaii

Chic 2-bedroom condo with resort-like amenities in awesome Honolulu

Conveniently located, contemporary condo is located in the center of Ala Moana. This beautiful 2-bedroom residence offers mountain views and unwind with dazzling city lights at night. Enjoy resort-style amenities, including two spas, poolside cabanas, a private dining...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

Walk to Ocean from house- close to BYU-H & Polynesian Cultural Cntr 3 bed 2 bath

Enjoy a slower pace in our family-friendly home, conveniently located only eight houses from the ocean in a local neighborhood close to Laie. We invite you to relax in our comfortable beds and huge cozy couch, or recline on the lanai chaise while reading a classic. When...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 9
📍 Hauula, Hawaii

Luxurious 2.5 Bedroom Unit with Panoramic Ocean View in ONE Ala Moana

This luxury unit has an epic panorama ocean view with floor-to-ceiling windows. ONE Ala Moana is the pinnacle of world-class living. This unit has 2 bedrooms plus a den, 2.5 baths, and 1 parking. One Ala Moana has a long list of luxury amenities and a great service team...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Honolulu, Hawaii

Luxury Ko Olina Oceanfront Villa O1105 w/ Stunning Ocean Views near Golf Course

Welcome to Ko Olina Beach Villa O1105 by Gather, a luxurious 3-bedroom, 2.5-bathroom retreat nestled in the heart of the stunning Ko Olina Resort in Kapolei, HI. This villa is designed for up to 6 guests and offers an exceptional blend of modern comfort and breathtaking...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kapolei, Hawaii

B209: Ocean Views from every room of this Ko Olina Beach Villa!

Beach Tower villa 209 has a spectacular view of the sunset! Its location is superior to all other units in the complex because it is truly beachfront. Beautifully decorated with high end furnishings, two very comfortable sofas and a beautiful dining area. The master...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kapolei, Hawaii

Waikiki Shore 1114

"This tastefully decorated island suite is fully equipped with everything you need to have a fantastic Waikīkī vacation. With a stellar location, you’ll enjoy gorgeous views of the Pacific Ocean and Waikīkī beach from your furnished, screened-in lanai. You’ll...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 HONOLULU, Hawaii

Ho'okipa Villa: Historic Home + Guest Cottage in Kahala

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Kahala Luxury Living Welcome to Ho'okipa...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 14
📍 Honolulu, Hawaii

Marriott Ko Olina Beach Club Studio -Read Description!

“This is a timeshare. While the amenities and features will be the same, you may not get the exact unit shown in the photos.”Units are assigned at check-in. Some units categorized as "Ocean view" may have obstructed view to the ocean.Welcome to our Marriott Ko Olina...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kapolei, Hawaii

Luxury Waikiki condo - 28th floor! Stunning views, convenient location, parking

Allure is one of the most luxurious private condominiums in Waikiki. The grounds, pool, and other amenities rival the resort hotels, but you get even more space, privacy and freedom. This property is ideal for couples or families seeking to feel at home in Waikiki for...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

Simply Beautiful Waikīkī Apartment

*MONTHLY RENTAL* Stay close to Waikīkī Beach, 5 minutes walk to the sand. Our stylish 2-bedroom space is in a secure building with free parking, pool, jacuzzi, sauna and rooftop BBQ area. Highlights include a big balcony, full kitchen, 3 air-conditioners, double...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Honolulu, Hawaii

^Marriott's Ko Olina Beach Club^ - 1BR 1BA MT. VIEW ^INSTANT BOOKING^ 1 car free

Marriott's Ko Olina Beach Club - 1BR 1BA MT. VIEW FULL resort access***INSTANT BOOKING***1st car park for free ($45 a day value)Full access to the resort’s services and amenities are included with every reservation.3 nights stay checking in on 3/11/2025 is for Ocean...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kapolei, Hawaii

Elevated Honolulu Sanctuary Renovated w/ Aircon

*** Disclosure: All rooms are renovated in a similar fashion. Furniture style may vary in pictures and in the unit. Functionality are all the same. Queen size bed in bedroom, sofa bed in the living room. Newly renovated in 2024Designer furnishedSecured & gated entry2...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Ilikai Hotel Partial Ocean View 2 BR Corner unit 18th Floor

(City View with City Flair) This first class accommodations in the world famous Ilikai Hotel is located at the gateway to Waikiki. This location is complete with a fully remodeled, spacious 2 bedroom, 2 bathroom and a beautiful views of the Pacific Ocean & City View of...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

Beautiful Mountain Views & Steps to Waikiki Beach

Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Dream of Aloha

— "This property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied." (PER CITY AND COUNTY OF HONOLULU). — This property cannot accommodate long...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kapolei, Hawaii

Spacious Home Near a Quiet Beach

Nestled in Waimanalo, this 2-bedroom, 1-bathroom vacation home brings it all within your reach. Fans of nature and the outdoors will love being within a 5-minute walk of Waimanalo Beach and 8 minutes by car from Bellows Field Beach Park. If you'd like to explore the...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 5
📍 Waimanalo, Hawaii

Rare 1 Bedroom Condo in at the Heart of Waikiki 2 blocks from the beach

Newly renovated in clean white with bright accent colors. Features a separate bedroom with it's own lanai. Full kitchen with full size refrigerator, stove, new built-in microwave, Keurig coffee maker, toaster, rice pot, utensils, pots, pans & bakeware. Bathroom has new...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Spacious 2 Bdrm Remodeled Oceanfront 01 unit

Above and beyond any other unit. Stunningly large with separate 2 Bdrms. Newly remodeled oceanfront condo on the Gold Coast. This is definitely the quiet end of the building and with the additional windows on the mountain side, you get incredible cross breezes all year....

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

Park Lane Ala Moana 7501

Welcome to Park Lane, an exquisite residential resort community conveniently located in the heart of Honolulu (direct elevator access to the world-class Ala Moana Shopping Center and across the street from Ala Moana Beach Park). The elegantly designed 3 bedroom, 3.5...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

Coastal Chic Condo with Ocean View & Full Kitchen

Step into a bright and airy beautiful condo, where modern elegance meets coastal charm. Expansive windows invite natural light to flood the open living space, offering breathtaking views of the marina and the sparkling Pacific Ocean. From your private balcony, enjoy the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Hale Mahina: Gorgeous Remodeled Pupukea Home with Private Hot Tub & Ocean Views

Enjoy the Flexibility of a Monthly Stay!This property is available for monthly rentals, offering you the comfort and convenience of an extended getaway. Whether you stay for a few weeks or the full month, you'll enjoy a consistent, all-inclusive monthly rate—no need...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Haleiwa, Hawaii

Lanikai Breeze – Contemporary Comfort Steps from the Shore

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Just steps away from coveted Lanikai Beach,...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii

Private Tropical Paradise in the Heart of the North Shore - beachfront community

[Oahu requires a minimum 30 day rental stay. All quotes will be returned for 30 days to ensure a valid stay duration]Aloha, we want to extend our home to your family to build great Hawaiian holiday memories on the beautiful island of Oahu.Located in the heart of North...

🛏 4 Bedrooms
🛁 1 Bathroom
👤 Sleeps 8
📍 Haleiwa, Hawaii

Waikiki Condo Has 2 Bedrooms & 2 Baths, with 1 free parking space.

This Waikiki condo was newly remodeled in June 2023, with 2 bedrooms, 2 full baths. The full kitchen has an oven, stove range, microwave, dishwasher and refrigerator, and includes fully stocked, large living room has a queen size sleep sofa/futon and 2 single full-out...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

Ho'omaika'i

This newly renovated, well-stocked two-bedroom, two bathrooms with loft space is fantastic getaway and a convenient, clean space for you home away from home with your family or friends. You can enjoy all that the North Shore has to offer and then come home to a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kahuku, Hawaii

Quiet North Shore Beachfront Home

This beachfront home is located in a quiet family neighborhood. Party animals, please look elsewhere! We are well off the main road with very little traffic making it a great place to take walks or go jogging. We are situated on a long white sand beach ideal for...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 10
📍 Waialua, Hawaii

ALOHA-WAIKIKI 2 Blocks 2 Shoreline of BEACH and Upgraded!!!

Located just two short blocks from the shoreline, this unit features a comfy queen sized bed, free wifi, a kitchenette, private bathroom and a private covered balcony from which you are able to enjoy mountain views and tropical breezes.Within our CLEAN PRIVATE unit, my...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Honolulu, Hawaii

Surfer's Paradise - Beachfront Vacation Rental on Oahu's North Shore

Welcome to Surfer’s Paradise by Gather, the ultimate beachfront vacation rental on the North Shore of Oahu. With its clean, spacious, and uncluttered space, Surfer’s Paradise is the perfect place to enjoy every second of your vacation. As you enter Surfer’s...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Haleiwa, Hawaii

Marriott Ko Olina Beach Club Ocean View 2 BDRM Villa

Currently we have this reserved for a one-week reservation sleeping up to 8. Check in on December 14 and out on December 21, 2019. Two-week option and flexible dates are available upon request. Located on one of four picturesque lagoons, Marriott's Ko Olina Beach Club...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 8
📍 Kapolei, Hawaii

Watermark - Luxury 2BD/2BA/2PA on 36th floor with an Ocean View!

Discover a breathtaking retreat perched "on top of the world" with wide-open ocean views that showcase Magic Island and Ala Moana Beach Park. Experience the perfect blend of indoor and outdoor living with a stunning, usable lanai to savor paradise every day.LIVING...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views

Recently updated with stylish contemporary design, this spacious Kailua home sits on Kailua Beach with nearly 100 linear feet of beach frontage. The home features direct and private access to the white sands with over 2 miles of beach walking at your front doorstep. 6...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii

Charming 1BR: Waikiki Banyan, Ocean View + Parking!

Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

We will block the property for 30 days but you can leave whenever you like

Designer steel, glass and titanium single family with Million Dollar Views, located few minutes from Waikiki, downtown, and walking distance to tropical forest trails.Has the feel of a tree house as you relax among centennial monkey pods.5 bedrooms, 5 + 2 half baths,...

🛏 5 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 9
📍 Honolulu, Hawaii

A Gallery of Views and Art at Waikiki

Imagine indulging in a Hawaiian vacation experience from the moment you wake up and open your eyes. Leisurely laze in bed as you enjoy sunrise through the wall-to-wall windows from a variety of angles. Watch the backdrop throughout the day like an ever-changing...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

Ko Olina Beach Villas B506 by Gather: Luxury 2BD 2BTH w/ Ocean Views

Discover the charm of island living at Ko Olina Beach Villas B506 by Gather, a magnificent beach villa in the heart of the renowned Ko Olina Resort. This exquisite two-bedroom, two-bathroom villa on the fifth floor, with space for up to six guests, offers a luxurious...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kapolei, Hawaii

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