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.
Ilikai 1 Bedroom Deluxe Lagoon View, Minutes to the Beach!
Perched on the 13th floor of the Ilikai Hotel, this spacious and newly renovated condo features modern furnishings and a brand-new king mattress for the perfect night's rest after a day of island adventures. Look no further—you've found your slice of paradise!...
#03 Kawela Kai 501:Updated NorthShore Beach Front-Relax & Unwind
LEGAL LICENSED SHORT-TERM RENTAL! CERTIFICATE:1990/NUC-2059 LICENSE# 90/TVU-0004 TAX MAP KEY: 1-5-7-005:007 This home is NOT affected by the new Honolulu County ban on vacation homes. Make sure when booking your vacation home the property that you are reserving has a...
the Birdcage - Waikiki Hideaway, Steps to the Beach
Location is everything!The Birdcage is a breezy and bright studio giving you clear views of the Koolau Mountains. With historic Waikiki Beach just outside the hotel lobby, the Birdcage is the perfect home base for exploring Honolulu and the rest of Oahu.Double paned...
Modern Waikiki Studio, 2 Beds, AC, WiFi, Pool & Fitness room
Escape to this fabulous studio in Waikiki, Honolulu. This welcoming retreat offers a peaceful atmosphere for up to 4 guests to unwind. With a cozy living area with 2 beds (1 Queen & 1 Full), a relaxing bathtub, and convenient amenities like WiFi and AC, this studio is...
Romantic Villa--Lovely Pond & Ocean View Studio
Our luxury condo is set in a tranquil location on the first hole of the famous golf course at Turtle Bay Resort. With a peek-a-boo ocean view, full view of a pond and the golf course, it is ideal for couples looking for a romantic hawaiian experience. In addition, the...
Spacious Ewa Beach Guesthouse On Beachfront Lot 30-day minimum.
30-day minimum stay by required by law. This property may not be rented for less than 30 consecutive days and rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied. No bookings of fewer than 30 days will be...
Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities
Oceanfront property is located steps from the Ocean in an upstairs large spacious private apartment with private entrance roughly 800 sq ft with breathtaking views of the Ocean, Mountains, Sea Turtles and other marine life out the large windows and the lanai patio. The...
Hauula Hawaiian Home - AC, Close to beaches,PCC
*30 day rental. Please inquire.You will discover the true Hawaii as you stay in this 3-bedroom, 1-bath Hawaiian home in Hauula. This newly-renovated bottom floor unit (the caretaker lives upstairs) getaway that sleeps 8-9 guests and is located about 5 minutes away from...
Ko Olina Beach Villas O521: Luxury Ocean View, 3 Bedrooms & Grand Lanai
Welcome to Ko Olina Beach Villas O521 by Gather, an exquisite luxury home nestled in the renowned Ko Olina Resort, offering an idyllic Hawaii escape. This beachfront villa with its stunning views is the epitome of island living. This three bedroom, three bathroom villa...
Stylish Ocean View Condo 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...
Ilikai Marina 1792 Ocean / Sunset / Fireworks Views King Bed, Sofa Bed
UNOBSTRUCTED SUNSET/OCEAN VIEWS! STEPS TO WAIKIKI BEACH. Walk to parks, shopping mall, restaurants, shops, buses, rental cars & Waikiki night life. Parking available. No smoking room. Clean and fresh high floor.UNOBSTRUCTED SUNSET/OCEAN VIEWS! STEPS TO WAIKIKI BEACH....
Free WiFi/No Resort Fees/Oceanview at the Ilikai Hotel! Beautiful Sunset Views!
1 Bedroom, Ala Wai Boat Harbor and Ala Moana Beach view on the 10th Floor! This condo was fully renovated from top to bottom with all new furniture & appliances! Open your sliding door to enjoy your morning coffee, afternoon cocktail or sharing an evening meal while...
SURFERS DREAM STUDIO
SURFERS DREAM! Private Comfortable Studio with private entrance, King Size Bed and comfortable amenities with a private deck and Outdoor Shower. This Studio is walking distance to one of Oahu's Most Beautiful Beaches on West Side and is located in a Private quiet...
#04 Kawela Kai 503: Updated NORTH SHORE Beach Front-Relax & Unwind
LEGAL SHORT-TERM RENTAL! NONCONFORMING USE CERTIFICATE:1990/NUC-2058 LICENSE# 90/TVU-0005 TAX MAP KEY: 1-5-7-005:007Make sure when booking your vacation home the property that you are reserving has a TVU#LIVE YOUR DREAM IN PARADISE AS YOU WAKE TO THE SOUND OF THE...
Beachfront Estate North Shore Oahu – Surf & Sunsets Await!
A Rare Opportunity To Stay in Hawaiian ParadiseNestled on the world-famous North Shore of Oahu, this stunning beachfront estate offers an unparalleled blend of luxury, comfort, and adventure. Whether you're looking to come to paradise with a group of friends or enjoy a...
ALOHA-WAIKIKI OCEAN VIEWS, POOL, FREE PARKING, SLEEP 4 and MORE!!! WB28
Large one bedroom Apartment has nice peeks of the Ocean & Diamond Head from balcony, bedroom & living room. FREE PARKING for one vehicle with this unit, Pool, BBQ and other perks on site makes this a great singles, couples and family destination within Waikiki AND only...
Spacious Family Home With Gorgeous Sunset Views of Diamond Head
This is a truly a local style experience property and the area of Kahala is full of the best of the best of locations on the Island of Oahu with everything close by: City Life , Awesome Beaches , Great Dinning , Tropical Hiking Trails & Views Galore , Look at the Famous...
Breathtaking Ocean Views Beach Cottage
This cozy cottage sits on a private white sand, reef-protected beach. Great for snorkeling and safe for kids! You'll enjoy swimming with turtles an a variate of colorful fish! Just sit on the serene sandy beach, enjoy the lush mountains, and captivating sunrises. You...
Just Renovated!! Spectacular Ocean & Diamond head View w/ Free Parking!
High Floor 1 Bedroom with the Spectacular View!!You can feel time goes by slowly and leisurely while you enjoy your stay in this unitThis room features full kitchen, large bath, High Speed Wi-Fi, and Television.In the morning, observe Waikiki waking up and the clouds...
9th floor Studio, Sleeps 2, Just 2 mins Walk to Waikiki Beach
Legal Vacation Rental is located at theWaikiki Grand Hotel®134 Kapahulu 922Absolutely awesome unit located just a block from the beach. in fact, you can see the ocean and the beach from the front door! Large Studio apartment with full kitchen and bathroom.Within our...
Seaside Paradise
This beach cottage located at the second level, is one of a kind. Please contact vrbo or owner for dates you are interested in if you don’t see availability. This cottage is so calming to just sit there and watch the ocean which is only steps away. Turtles frequently...
Charming Studio Apartment with WiFi, AC in beautiful Diamond Head Beach Park!
Enjoy a peaceful stay at this wonderful studio apartment on the Gold Coast. The space features a queen bed and open floor plan. The bathroom includes bath and shower combo. In the additional living space, there's a comfy sofa bed for extra guests. Fall in love with this...
Waikiki Banyan 1909 Amazing Views and Just Steps to the Beach
Waikiki Banyan 1909 Amazing Views and Just Steps to the Beach Beautiful Views of Ocean and Diamond Head, Relax on the Lanai with a tropical drink and enjoy this Beautiful view's 1 Block to Waikiki Beach. Full Kitchen equipped just like home Bedroom has a Queen and Twin...
Steps to Waikiki Beach! Newly Renovated w/ 75" TV
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...
BEAUTIFUL Ocean Views! A/C, Wi-Fi, Washlet, Pool, one Parking!
Waikiki Sunset #2904 – 229 Paoakalani Ave.Fabulous views of the Pacific Ocean, Diamond Head and Kapiolani Park from this 29th floor, one-bedroom condo (564 sqft plus lanai with table and chairs) with central AC. 4-person max.Just a 10-minute walk to the best swimming...
Enjoy Beachside Living! Relax at the Popular Colony Surf #307
*Check-in Assistance Fee for Colony SurfFor check-in assistance outside of Aska Gateway's operating hours (9 am - 5 pm HST Monday through Friday) and on federal and state holidays, the check-in assistance fee is $200 (plus tax).**There is a water shut-off scheduled in...
Waimea Bay Luxury Estate Views & Hot tub
Summary:Immerse yourself in the ultimate Hawaiian experience at Waimea Bay Luxury Estate, located on a corner bluff lot in the peaceful neighborhood of Pupukea on Oahu's North Shore. This expansive estate boasts breathtaking ocean views from every angle and is just...
Waikiki Studio with Stunning Views!
As of January 1, 2026, Hawaii will increase its Transient Accommodations Tax (TAT) rate by 0.75%. For reservations booked before January 1, 2026, an additional payment request will be sent for the 0.75% tax increase.This is a legal conforming vacation rental. Please see...
Turtle Bay Perfect Family Destination, Kuilima West
Welcome to Your Dream Vacation at Turtle Bay!Our Kuilima West condo, is ideally situated just steps from the Turtle Bay Ritz Carlton Resort, Lei Lei`s restaurant, scenic walking trails, world-class golf courses, and the stunning beaches of Oahu`s North Shore.Discover...
Ocean-Marina Yacht Views Condo Steps to the Beach w/Full Kitchen & Free WiFi
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.July 11, 2025ILIKAI MARINA NOTICE — Spalling Work UpdateSpalling repair on the Ocean/Marina-facing side is nearing completion, but...
Beautiful condo with amazing view, huge wrap around balcony and designer decor!
Come enjoy your Hawaii vacation at our beautiful newly remodeled condo. The views are spectacular and the wrap around balcony gives a 360 degree view of the ocean and mountains. This unit is very spacious and has a decorators touch! The unit is fully equipped with...
Renovated and clean studio in Waikiki for two with amazing views
Walk to Waikiki beach, convention center, Ala Moana mall, restaurants, shops and many other Waikiki attractions in this newly renovated unit with a queen bed, full bath and kitchenette. The building offers a pool, Jacuzzi, large sun deck, barbecue grills, gym (one time...
Gorgeous 2 bedroom with a stunning ocean view
LOCATION!!! This condo puts you right on Waikiki Beach with a view to match. The interior boasts a spacious floor plan of over 1,000 sq ft with full kitchen, work space and large lanai. With a fully stocked kitchen you can choose to enjoy home cooked meals on your...
North Shore Garden Studio
Enjoy your bright light garden apartment on an acre of lush north shore. Nearby hiking trails, pristine beaches, dining, and shopping within minutes. Close to Haleiwa town, Waimea Bay & Valley, Sharks Cove, and the best surf spots in Hawaii. Private entrance and lanai...
3BR for the Price of 2. Golf Course View & Golf Cart too!
Gated resort community with 4 white-sand ocean lagoons, Ted Robinson golf course, spa, hotels, restaurants, marina. Ko'Olina is a quiet community, with pool/hot-tub/BBQ at the rec center. This condominium has beautiful Coconut hardwood floors throughout and is fully air...
Kuilima Estates East #164: Mountain View Condo w/Shared Pool, AC & Near Beach
Live the ultimate paradise experience on Oahu's renowned North Shore at Kuilima Estates East, unit 164. Experience this cozy one-bedroom, two-bathroom townhome that overlooks the stunning Turtle Bay Golf Course. Boasting an unobstructed view of the 18th hole on Fazio's...
Peak-a-Boo Ocean & Sunset Views, A/C, Wi-Fi, FREE Parking, Close to Beach!
Waikiki Sunset #906 – 229 Paoakalani Ave.Enjoy colorful Hawaiian sunsets from your private lanai! This cozy rental features central A/C, a full kitchen, free Wi-Fi, and a pool, gym, BBQ area, and coin-op laundry facilities on each floor. Just a quick 4-minute walk to...
Kuilima Estates West #120: North Shore Golf View
End every day with a stunning Hawaiian sunset on the North Shore of O’ahu when you stay at Kuilima Estates West, unit 120. This newly remodeled 2-bedroom, 2-bathroom with loft townhome is located adjacent to the Turtle Bay Golf course, home of the Fazio and Palmer...
Ho'omaha Haven, Modern Remodel, 2 Kitchens, A/C
Welcome to our 5-bedroom modern retreat on Oahu's sunny west shore! This is a top/bottom duplex with separate entrances and is rented as a whole home. There are three bedrooms and two bathrooms upstairs and two bedrooms with a third bathroom downstairs. This newly...
Gorgeous new listing! Half-block from Waikiki Beach!
Be one of the first to stay in this gorgeous new listing! This spacious 2 BR, 2 BA condo is steps from beautiful Waikiki Beach. Located in a quiet residential building, situated among Honolulu's finest hotels, it combines an alluring tropical setting with modern...
Honolulu Vacation Condo, Near Beach + 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...
Absolutely Oceanfront - 60' Waterfall Lap Pool
Kailua Absolutely Oceanfront Deluxe Legal Vacation RentalThe closest house to the Ocean in KailuaLocated in a quiet upscale neighborhood away from the crowdsHear the waves breaking just outsideGo tide pooling steps away60ft salt-sanitized waterfall lap poolDramatic...
Breathtaking Ocean Views - Waikiki - Ilikai Marina
Construction Notice 5/30/25: Spall repairs are currently underway on the mountain-side units. Please be aware that construction noise may occur between 8 AM and 4 PM. Access to the lanai will be restricted until early September. The project is expected to be completed...
Gorgeous Diamond Head Views from 34FL 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...
Ilikai Hotel - No Resort Fees! City-views, condo on the 14th Floor, Prime Waikiki location!
This condo is located on the 14th floor of the Ilikai Hotel. With over 500 sq ft of living space, the condo is extremely spacious and comfortable for couples, friends, or family traveling together. Bye, bye carpets; the condo recently installed new vinyl flooring! Stay...
Spacious 1 Bedroom Condo w/full Kitchen & Parking
Located just 2 mins walk to the sands of Waikiki Beach and the Pacific Ocean, our condo offer 1 Queen bed in the bedroom and a futon in the living room to sleep a total of 4 guests.The full kitchen makes cooking at home a breeze should you want to watch the budget.We...
34th Floor Ala Moana Large Regal Suite - 2Br/3Ba, Book Now at Special Rate!
Here in our 34th floor 2 bedroom/3 bath Regal Suite at the Ala Moana Hotel condo, you will experience island-style comfort in one of Hawaii's most convenient locations. This unit is located very close to the beaches and the state's largest shopping mall, Ala Moana...
Amazing ocean and sunset views
This beautiful guest house is located on Maili Point, one of Oahu's most scenic sites. Maili Point is located on the dry and sunny west side of Oahu giving days of perfect weather, full of sunshine and trade winds. The property's secluded location provides a relaxing...
Ilikai Hotel #940, Lagoon view, Free WIFI
Your dream vacation awaits! As soon as you step through the doors, you'll realize you've found PARADISE!! This condo is located on the 9th floor of the Ilikai Hotel. You'll love the renovated bathroom, completed in September 2024! The condo also...
Luxury Ilikai 2-bedroom 2-bathroom Unit NO RESORT FEES! FREE WIFI
Best 2-bedroom, 2-bathroom city view Ilikai unit!Great deal for a world-famous Ilikai unit over 1000 s.f. with two lanais to enjoy some cool ocean breeze.It is tastefully furnished with all you need for a comfortable stay in paradise.The Master bedroom has a king bed,...