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.
From world-famous beaches and luxury resorts to quiet towns and hidden coves, Oahu offers a wide range of vacation rentals to match your travel style. Whether you want a high-rise with Diamond Head views or a secluded cottage near the waves, you'll find it here.
In Waikiki, experience vibrant city life, surfing, nightlife, and shopping-all within walking distance. Families and upscale travelers alike love the Ko Olina area in Kapolei, known for its protected lagoons, golf courses, and luxury villas.
The legendary North Shore delivers laid-back beach towns, world-class surf, and open landscapes. Here you'll find spacious rentals near Kuilima Estates and Turtle Bay, perfect for outdoor adventure and ocean lovers.
For a more peaceful setting, head east to the windward side. Kailua and Lanikai are favorites for couples and families seeking calm waters, beach walks, and a more local vibe. On the northwestern shore, Waialua provides a rural escape away from the crowds, ideal for a quiet and reflective stay.
Why Choose Oahu Vacation Rentals?
- Wide variety: from beachfront condos to private villas and family homes
- Full kitchens, lanais, air conditioning, Wi-Fi, and pools
- Convenient access to beaches, hiking, dining, and shopping
- Pet-friendly, extended stay, and snowbird-friendly options available
- Great for couples, groups, digital nomads, and first-time island visitors
Popular Areas for Oahu Rentals
- Waikiki – Iconic beachfront condos, shopping & surf
- Ko Olina – Luxury villas and family-friendly lagoons
- North Shore – Surf culture, remote beaches, and nature
- Kailua – Calm waters and laid-back Windward vibes
- Waialua – Secluded retreats and country charm
Explore all available Oahu vacation rentals below and start planning your perfect island stay today.
Upscale Penthouse with Ocean Views & Free 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...
M. KoOlina Beach Club Oceanfront Resort, Beautiful, Tropical Oceanfront Retreat!
Please choose a Friday through Sunday check-in for a seven night stay. Rates are based on a garden view and will fluctuate for holiday weeks. Thank you for your interest in booking with Dash Realty Group, Windermere Florida. Dash Realty Group is registered in Florida as...
Ocean & Diamond Head Vu; Full Kitchen; Free Wifi; 2 min. walk to the beach
Legally permitted rental - 2450 Koa Ave #92Located in the heart of Waikiki steps from the beach, at The Seashore. On the 9th floor of a 10 floor building, near the Hyatt Regency and the Duke Kahanamoku statue. This beautifully and comfortably furnished ocean and Diamond...
Completely upgraded, Beach Tower 3 Bedroom. Last minute discounts 4/19-5/21/25.
100's of reviews available. Contact host. This elegant villa is located on the 4th floor of the Beach Tower just one back from direct oceanfront. Close to the waters edge at Lagoon 2, it boasts an ideal location nestled above the lagoon pool/BBQ/beach bar area and...
BIG ALOHA & AWESOME VIEW AT THIS HAWAIIAN HOME!
~Breezy Spacious and Welcoming Vacation Home~This Hawaiian home sits up on the mountain with unbelievable, panoramic views of the Pacific Ocean, Diamond Head, Waikiki, and downtown. Watch sunsets, fireworks, whales, and rainbows from the lanai. Situated only 2 miles...
Beautiful Ocean and Diamond Head Views w/ 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...
Newly Renovated Studio Apt, close to Hukilau Beach, with AC & WIFI, 30-day
This cozy studio apartment has recently been renovated and is ideal for 2-3 people.You'll love the proximity to beautiful Hukilau Beach-an easy 5-8 min walk. Delicious Restaurants and food trucks are near by but there is a cook-top and other kitchen appliances provided...
Manoa Valley A 2BR with ocean and mountain views
Permit 90/BB-0065Located on a hill overlooking Honolulu and the majestic Diamond Head crater, this two bedroom, two and half bath plus bonus sleeping space in Manoa Valley features gorgeous custom touches and a large lanai that’s perfect for a barbecue. The home is...
Great for Families! Partial Ocean/Canal/Diamond Head Views! Pool, Wi-Fi, Prkg
Fairway Villa #2217 – 2345 Ala Wai Blvd(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Your Home Away from Home! Enjoy this recently remodeled contemporary two-bedroom, two-bath condo (723 sqft plus 151-sqft lanai) with great views! Sleeps up to...
Slice of Heaven Studio
A newly renovated self contained 300 sqft studio that is a short 5-7 mins walk from our local quiet beach. The tastefully decorated studio has modern amenities and is comfortably furnished finished with a beautiful marble floor and bathroom. Studio has its own entrance...
Oceanfront Getaway on Oahu North Shore
Feel your stress melt away in this gorgeous 3-BR, 2-BA oceanfront sanctuary! House is in a gated community on the fabled Oahu Northshore. The secluded, aqua-blue waters of Kawela Bay are in your own backyard—swim, snorkel, surf, paddleboard, kayak and sunbathe...
Sweeping Ocean Views, Remodeled, Steps to Beach, Washlet, Parking! Sleeps 4.
Waikiki Shore #1212 – 2161 Kalia Rd.Waikiki Shore is the only condo in Waikiki where you can step directly from the building onto the sand of Waikiki Beach!You'll be mesmerized by the incredible ocean views from this beautiful Hawaiian feel contemporary. The open...
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...
Stunning Kawela Bay Beachfront Home - 3 bedrooms - sleeps 9
***In accordance with local laws, we may accept one booking for every thirty day period. Pricing may vary depending on length of stay and time of year. For questions or assistance with booking, please contact us.This lovely beach house is casual, stylish, and chic with...
Beachfront, Peek-a-Boo Ocean Views, Washer/Dryer, A/C, Wi-Fi!
Waikiki Shore #308 – 2161 Kalia Rd.NEW TO OUR INVENTORY! You'll adore this beautiful one-bedroom condo (706 sqft) right on the beach in Waikiki! Just imagine stepping right from the building onto world famous Waikiki Beach! After a day shopping or relaxing on the...
Ko Olina Beach Villas 609: 2BR Villa w/ Stunning Beach Views from Every Window
Step into the world of beachfront luxury at Ko Olina Beach Villas B609 by Gather, a rare gem in the stunning Ko Olina Resort. Located on the sixth floor at Ko Olina’s 2nd Beach Lagoon, this two-bedroom, two-bathroom villa accommodates up to six guests and is one of...
Turtle Bay Corner Condo Overlooking the Fairway - Kuilima Estates East
Enjoy the best of what the ‘fabled North Shore’ has to offer in this authentically designed Hawaiian-beach-themed unit, that sleeps up to four (4) adults, with Resort-style amenities at your doorstep, including snorkeling beach access, swimming pool, tennis courts,...
NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01
Start your day with a stroll on one of the most beautiful beaches in the world. Enjoy the sunrise in Kailua where your Hawaiian holiday truly begins. Kailua Beach is a perfect place to go to 'get-away-from-it-all.' Swim, boogie board, surf, kayak, sail, or windsurf in...
Stunning Ocean View 1BR Condo - Free 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...
@ Marbella Lane - 2 master suites | MT+Ocean Views
Summary:Make beautiful memories in this spacious 4 BR home with 2 master suites, located in a gated community with 24 hours security. It is within the greater Waianae area, right in the heart of the Makaha Valley. On the Leeward side of Hawaii where the Ocean Trade...
Ocean and Diamond Head views from quiet end of Waikiki Beachfront!
Colony Surf #908 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)This sunny, 540 sq.ft. tropical décor studio has wonderful views of the Pacific Ocean and Diamond Head! During winter...
Call Diamond Head Hidden Paradise booking req.
Call/ sms direct 4152519696 other than 30-days interest for accurate rates and availability. Reservation from the platform is limited.Hidden Diamond Head Paradise located in the Diamond Head District, is nestled above world famous Waikiki Beach, in a secluded, tropical,...
Tropical Turtle Bay Condo - Kuilima Estates East
This newly listed unit features a loft bedroom, with a large kitchen and living room. Unit is located right on the Arnold Palmer golf course and a 5 minute walk or 2 minute drive from Turtle Bay Resort. Enjoy luxury gated community amenities featuring gated access,...
Hale Lani ~ Heavenly Home
This beautifully decorated one bathroom with a loft is the perfect space for your next family vacation! This well-appointed unit has a king bed in the primary bedroom downstairs with a full bathroom. There is a flat screen smart TV with Spectrum cable access, ceiling...
Cozy Kaaawa Studio with Mountain Views - 30 Day Min
This country studio is close to family-friendly activities, public transport, the beach, 7-11, hikes, Uncle Bobo's, waterfalls, and mountains.. You’ll love my place because of the people, the neighborhood, the tranquility, the stars, the sound of the ocean, the views...
Luxury Ko Olina O1002 Spacious 3BR : Ocean and Mountain Views
Luxurious Penthouse 3 Bedroom Sleeps 8(1king,1queen,2twin, (+2twin airbeds)) , 2.5 Bath (3toilets ,2 shower, 2 tubs ), 2 Parking Unit Ko Olina Beach Villas | Kapolei, Hawaii Newly Upgraded (Oct 2024): Washer, dryer, and dishwasherNew sofa (April 2025 )Villa...
Amazing views of Diamond Head, Waikiki Beach, and the Pacific Ocean!
UNBELIEVABLE VIEWS!: This 2 BR condo is on the 35th floor of the Waikiki Sunset. It offers unmatched views of Diamond Head and Waikiki Beach. No expense was spared in this condo's remodel. Bold granite highlights the custom cabinetry and stainless appliances. Designer...
Secluded Sands ~ Private Beach Access, A/C
Head to the tropics of The North Shore and see for yourself why our guests describe our destination/vacation home as an "island paradise." Our spacious beach house, with 5 bedrooms and 3 full bathrooms, has access to one of Oahu's few remaining, truly secluded beaches...
Oasis at Turtle Bay Condo on the North Shore - Kuilima Estates West
This homey one bedroom (cal king bed) with upstairs loft (with one queen and one twin bed)/two bathroom Turtle Bay condo offers the perfect true Hawai'i get-away for up to five! It's close to the public beach at the Turtle Bay hotel, sitting on the 1st hole of PGA Fazio...
A View to Die for! 3 bedroom 3 bath on the sand at Waikiki Beach
Discover the little known secret of one of the most prized stretches of Waikiki Beach. The only privately owned condominium in Waikiki where you can step right from the building onto the sand of world famous Waikiki beach. If you're seeking Hawaii sunshine with the view...
Paradise by the beach
This is a beautiful 5 bed, 3 bath home that sleeps 12. It is located just steps from famous Hukilau Beach, and within walking distance from BYU Hawaii. There is a washer and dryer, two living rooms, office and much more. Enjoy a sunrise stroll on the beach, spend the...
Bright Corner unit with Stunning Views! AC, W/D, Wi-Fi, Washlet, parking!
Four Paddle #2302 – 2140 Kuhio Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)You'll love the stunning views of this 23rd floor one-bedroom corner condo (577 sf plus partial ocean-view lanai with table and chairs)! With central AC, this...
Waikiki Banyan OCEAN VIEW Plumeria Suite - lots of amenities, free parking, Waikiki Beach
Enjoy breathtaking ocean views on the 30th floor!Want to be steps away from the beach, indulge in a fully-equipped kitchen to cook any meal, and relish in the astonishing ocean views from a wonderfully remodeled 1 bedroom unit at the Waikiki Banyan?Welcome to the age of...
Sunset Pt. BEACH Cottage/ almost beachfront w yard, bikes for 2 guests only.
Adorable with yard , locking gates, and privacy, and next to the beach ! The Beach Cottage is almost beach front with lovely outside space, deck, bikes, AC, and more.Located in it's own yard on the tip of Sunset pt with private yard & parking. Please inquire w total #...
Spectacular Condo: 2BR/2BA Oceanfront
This VERY NICE irresistible, 2 bedroom, 2 bath condo is our home away from home for a portion of the Winter. It is on the water and has a stunning ocean front view. The unit has been newly painted and updated. The freshly updated kitchen includes new cherry cabinets;...
Ocean View Home Near the Beach and the Golf Course in Secure Gated Community
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.May 2025 the Community Pool, Jacuzzi, and Gym are now OPEN!!Newly Built 3-bedroom 2.5 Bath home in a quiet and 24/7 gated community....
WaikikiLux 509 Waikiki
Our side by side units are located right in the heart of Waikiki where almost everything you desire is within walking distance, great for families or business associates traveling together. Clean updated fully equipped units. Full kitchens, linens, bath/beach towels,...
Modern 2BR w/Diamond Head view, beach, FREE parking, king bed, pool, gym,& more!
Two bedroom condo with beautiful Diamond Head view in the heart of Waikiki, with full kitchen, living room, and balcony(lanai). Bedroom one features king bed, and small desk/workspace. Bedroom two features two twin beds. Sofa pulls out into a bed in the living room....
Modern, Ocean View In a Great Location In Waikiki!
NEWS FLASH! This condo has recently removed the carpet & install LUXURY vinyl flooring! Modern and elegant in style, this updated and spacious condo will ensure a comfortable and luxurious stay at the Ilikai Hotel. Located on the 4th floor, you'll enjoying watching the...
Ground Floor Beach Condo Spectacular Views AC in Bedroom 30 day Minimum Rental
Welcome to Coastal Living at Its Finest! Stylish ground-floor condo with unobstructed ocean views and direct beach access in a quiet oceanfront complex — this 1-bedroom/2-bath unit has been remodeled and is loaded with high-end upgrades. Amenities include high-speed...
Bamboo Waikiki #207. Spacious one-bedroom condo located in a tropical oasis.
Bamboo Waikiki #207. Spacious one-bedroom condo with a Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) King bed, (1) Queen sofa sleeper, (1) Twin sofa sleeper; Sleeps 5.Spacious one-bedroom condo located in a tropical oasis in the heart of...
~Waikiki~ LOWEST RATES IN AREA ~ 3 Bedroom ~ Fully Furn ~ Blocks to Beach ~
We offer our Hale to you to enjoy the benefits of staying in one of the largest Apts. in our surrounding location, right in the Heart of Waikiki.Our large open floor plan is fabulous featuring a living/dining room combo. All 3 Bedroom apts. have a private lanai for your...
Stylish Unit Near Waikiki Beach with Free 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...
Ko Olina Beach Villas O822: Elegant Retreat, Lagoon Views, Spacious Lanai
Welcome to Ko Olina Beach Villas O822 by Gather where luxury meets the serene beauty of Hawaii. Situated in the Ocean Tower at Ko Olina Resort, this villa is a stone's throw away from a well-groomed lagoon, offering guests an intimate connection with nature's wonders,...
Oceanfront Beach House - Tropical Paradise!
Oceanfront Beach House - Tropical Paradise!Our Tropical Paradise is oceanfront and conveniently located between historic Haleiwa and Waimea Bay at the world famous Chuns Reef beach. Great swimming, snorkeling, scuba diving, and surfing are right in the 'front yard.' Our...
Turtle Bay - Relax In Paradise - Kuilima Estates West
Aloha ! Welcome to my condo located at 57-101 Kuilima Dr. Kahuku Hawaii 96712. My condo is clean, well maintained, and comes with many amenities . Some amenities are Tennis rackets, bodyboards, snorkel and mask sets , beach towels, beach chairs, and more. Full access to...
SPECTACULAR OCEAN VIEW! A/C, Wi-Fi, Pool, FREE Valet Parking, Steps to Beach!
Waikiki Beach Tower #2001 – 2470 Kalakaua Ave.If you'd like to be directly across the street from the best swimming and surfing beach in Waikiki, then this two-bedroom, two-bath Waikiki Beach Tower condo with 1150 sq.ft. interior living space (and a large 160 sq.ft....
Ocean View Guest Cottage - 1990/NUC-1797
Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply.A two-bedroom, one-bath, ocean view cottage located a few steps from Kailua Beach... Voted Number One beach in America! There are 2 shopping...
Private Waterfront House AC & Fast Wi-Fi 30 Day
This house is all about being right on the water. A seawall provides protection from waves at high tide. A North Shore Beach House with the comforts of a nice home ideal for long term stays. Local pickle ball played right down the street. 30 Day Minimum ContractIncluded...
Expansive Ocean View! FABULOUS Location and Building Amenities!
Discovery Bay #3019-Resolution Tower - 1778 Ala Moana Boulevard(30-night minimum) ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.FABULOUS OCEAN VIEWS, FREE PARKING, WASHER/DRYER - THE BEST OF MONTHLY RENTALS! This spacious, 852 sq.ft. one-bedroom corner condo at...