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.
Pua Oriana: A Polynesian Tropical Retreat
E komo mai — welcome to our hale. Welcome to the Pua Oriana – a mix of Hawaiian and Samoan language, ‘pua’ meaning flower, and ‘oriana’ means the flower that adorns a woman’s head. Enjoy the space and the grounds with 880 acres of pristine gardens, walking paths, golf...
Ocean View Studio - Polu Hale - 2 min Walk from Beach
Enjoy your vacation in Hawaii in this beautiful and spacious studio with gorgeous turquoise ocean view. Indulge in luxurious amenities like a romantic king size canopy bed, a huge 47' LCD TV, a well equipped kitchenette with granite counter tops, a rock vessel sink in...
Tranquil Sandy Beachfront - minimal beach traffic. Like your own private beach
This home's 1700 square feet interior is newly remodeled and has 3 bedrooms, 2 bathrooms. Two bedrooms have queen size beds and one bedroom has 2 twin beds. The bedrooms and living rooms have ceiling fans or you can enjoy the cool ocean breezes. The living room has two...
Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage
Enjoy a restful respite in this private cozy cottage with a beautiful private garden. The Lanikai Bungalow is a private separate cottage. It has one bedroom with beautiful relaxing living spaces, full kitchen and bathroom. The cottage has a gorgeous private lanai/patio...
Renovated Waikiki Studio! City View, Full Kitchen, Free Wi-Fi & Parking, Pool
Fairway Villa #811 – 2345 Ala Wai Blvd.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)NEW TO OUR INVENTORY! You'll enjoy this modern, renovated (April 2023) 8th-floor studio in the quieter east end of Waikiki. With a full kitchen, free Wi-Fi, and...
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.Custom stained...
New Listing! Marina-front Home Near the Ocean w/Private Pool & AC: Nani Wai
Nani Wai is a five-bedroom, four-bathroom private retreat tucked into the prestigious Hawai‘i Kai neighborhood of Honolulu, O‘ahu. With its enviable waterfront perch on a private marina and unobstructed views of Koko Crater, this gated home delivers a seamless blend of...
Fairway Villa Waikiki Rental (30 day min)
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Fairway Villa Located at 2345 Ala Wai Blvd. 11th FloorLiving/Dining Area- 1 Couch (not a sofa bed)-...
Modern remodeled 2bdrm/1bath Condo/Free Parking on Property/Sleeps 6/Great Views
The best things about this condo: Stunning views from the 14th floor lanai (Mountain and Valley/Ala Wai Canal/Manoa Rainbows), convenient free parking on premises, save money by eating in, clean with modern decor, and within walking distance to all that Waikiki has to...
"Pineapple Perch" | Fully Renovated | A/C in Every Room
Welcome to your ultimate escape on Oahu's legendary North Shore. This spacious 3-bedroom, 2-bathroom home delivers modern comfort wrapped in laid-back island charm, making it a top pick for families, visitors of BYU Hawaii or the Polynesian Cultural Center, or anyone...
Chic Mountain View Unit Near Waikiki Beach+Parking
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Get ready for a fun tropical getaway in this beautifully remodeled 1-bedroom corner condo on the 10th...
Last minute discount, 4/26 - 5/12. Huge 3/3 Oceanfront Penthouse
This beautiful Ocean Tower 10th floor Penthouse end-unit is huge, recently renovated, and has a unique floor plan with glass doors on both sides of the main living area that slide completely into the walls, creating a wide open space more than 75 ft wide with east,...
3BR Ocean View Condo w/ FREE Parking, WiFi, Walking Distance to Waikiki Beach
3 Bedroom unit located on the 20th floor of a very popular condo. The unit is located in the heart of Waikiki, walking distance to Waikiki Beach, shopping, Honolulu Zoo and Waikiki Aquarium and fine dining restaurants. (World famous Hy's Steak house is located in the...
Bright, breezy, upgraded house, near the ocean! Contact for rates/availability!
This is a short-term vacation rental. Welcome to Hale Alapi'i, our home in fabulous Lanikai!This is a 3b/2b ~1,400 sq. ft. main house that sleeps 4 adults or 2 adults + 2 kids comfortably, on a slight uphill to enjoy beautiful Hawaiian scenery, tropical birds and island...
16P - Permitted penthouse end unit at the Hawaiian Princess - best view on Oahu
Hawaiian Princess 1 bedroom, 1 1/2 bath end unit penthouse. There is no better ocean/beach view on the westside of the island than from the lanai of this 16th floor condo. This condo sits right on the beach. 850 square feet inside the condo, and 400 square feet of lanai...
Zen Oasis Waikiki - Oceanfront Penthouse
Wake up to endless ocean horizons! This Zen-inspired penthouse marries sleek design with soothing décor for a truly restorative stay.Private lanai overlooking Waikiki BeachKing-size bed & fast Wi-Fi for work-cationsSteps to surf, dining and nightlifeAs Superhosts we...
Base of Diamond Head, Full Ocean View, 8th Floor, Private, 6 month special
Book 'em, Danno30 Night minimum booking is required. Available June 1, 2026Inquire about 6 month or longer rentals.Experience TRUE ALOHA in this condo that was home to James MacArthur, the original Danno of Hawaii Five-0, and is still owned by the MacArthur family. This...
Enjoy the Gorgeous Mountain, Canal and Golf Course Views #2120
* Please note: the shower temperature may fluctuate between warm and lukewarm even after setting it, but it’s still fully functional for showering. * Please be advised that there may be unplanned water outages without prior notice from the building management.Important...
Ocean front 1-bedroom house, good location with AC, WiFi
Steps from the ocean. Escape to a cool 1-bedroom house by the Beach. This excellent property features a cozy queen bed, AC, WiFi, and a sofa bed. Guests can unwind in this serene space, just a stone's throw away from the beach. Kick back, relax, and enjoy everything Ewa...
New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach
One Rate for 7 up to 30 day stay - A 30 day minimum lease.Hawaii Tax ID # available upon requestMountain View's cooling breezes , easy 5 minute walk to world-renowned Kailua Beach makes this an ideal, relaxing alternative to the typical busy "touristy" destinations of...
30FL Great Ocean Views w/ Lanai, King bed, Parking
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Welcome to your island retreat at Waikiki Banyan. This recently renovated 600 sq ft corner condo on the...
Kailua Home Pool & Spa with amazing views
Two story home in Quiet Kailua neighborhood. Master bedroom is overlooking a beautiful pool and spa with views over the town of Kailua and the ocean. Upper family room has a pool table and also a fantastic view of Kailua town & ocean. Entire home was built in 2008 and...
Stylish 1BR Apartment with AC, Full Kitchen & W/D - Just Steps to the Beach
Welcome to our newly renovated 1-bedroom apartment in Kailua, Oahu. This rental offers everything you need for a comfortable stay, providing a family-friendly atmosphere that will make you feel right at home.Whether you prefer to barbecue on the covered lanai or take a...
Beachfront Beach Villas at Ko Olina O-501
Summary:Beach Villas at Ko Olina is about a couple miles stretch of coastline in this resort area. Four lagoon beaches that is shared with Disney Aulani, Four Seasons and the Marriott Vacation Club. But, the Beach Villas sits on "Honu" Lagoon which is basically...
Hale Healani B-705 Stunning Views of the ocean Free Parking
Oceanview Luxury Villa at Ko OlinaWelcome to your oceanview beach villa at the exclusive Beach Villas at Ko Olina. Surrounded by lush koi ponds, cascading waterfalls, a lagoon pool with a sandy beach, an infinity lap pool, and multiple hot tubs, this resort offers a...
Spacious 2BR Partial Ocean View O410 Resort Living at Ko Olina Beach Villas
Luxurious Condo - 2 bedroom(1 King size bed, 2 twin-size beds, and a pullout sofa bed.) , 2 bath, full kitchen Sleeps 6This 2-bedroom luxury villa is located on the 4th floor of the Ocean Tower facing the Aulani hotel and mountains . It is easy to access to the pools,...
Ocean Escape by AvantStay | Ocean Views | White Sandy Beaches | Brand New Home
Indulge in the Unmatched Beauty of Contemporary Luxury at Ocean Escape — A Brand-New Retreat!Discover the newly constructed, unparalleled, modern, luxury, three-bedroom house, where every corner is adorned with awe-inspiring ocean views. This Hawaiian haven transcends...
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...
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...
Luxury 3-Bedroom Villa with Expansive West Views of Ocean and Lagoons
Your vacation starts once you arrive at the Ko Olina Resorts with a big smile and friendly wave entering the 2-mile community of premium coastal views, four crystal-clear lagoons with white-sand beaches, a championship golf course, and a full-service marina for...
Island Jewel — Ocean Front North Shore Paradise
An island jewel on the North Shore of Oahu, this cottage is situated right on the water in a quiet, serene, and peaceful setting. Surrounded by palms and gentle trade winds, the cottage is located in a gated, old-style Hawaiian setting, offering all of the amenities...
Family sized condo minutes walk from beach and golf course in Ko Olina Kai.
HOA rules (for ALL residential condos in Ko Olina, not just ours!) restrict rentals to 1x/30 days and Hawaii State Laws requires stays of 30 days or longer.This comfortable and spacious villa can accommodate 6 guests in a gated community with its own private pool. it is...
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...
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...
Partial Ocean View King STUDIO with Kitchenette and FREE WIFI!
Aloha from Waikiki! We are a short-term vacation rental company, we are not part of the hotel. The Royal Garden is located at 440 Olohana St., walking distance to everything. Take a short stroll to Luxury Row on the Waikiki "Strip", and the Ala Moana Shopping Center or...
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...
AMAZING COUNTRY RETREAT ON THE COVETED NORTH SHORE!! Enjoy creating memories with your family and friends at our favorite place in the world. Surf, hike, swim, snorkel, take in the rays!!! This private estate offers ocean views just up the hill from world renowned...
Beachfront, Sweeping Ocean Views, A/C, FREE Parking and Wi-Fi, Washlet!
Waikiki Shore #1208 – 2161 Kalia Rd.You'll fall in love with the spectacular ocean view from this beautifully renovated one-bedroom condo (820 sqft) right on the beach in Waikiki! Just imagine stepping right from the building onto world famous Waikiki Beach! Then, after...
🏝️Lanihonua - 2br +Office - Ground Floor Villa - Christmas in Ko Olina
Everything you want in a luxury beach rental! Great amenities, fantastic owner direct service!Virtual Tour: https://my.matterport.com/show/?m=EyRF7RHrerd&back=1Check out our reviews and photos and then compare to a stay in a tiny hotel room! Lanihonua villas are a...
Beachfront Cottage on North Shore Oahu, Sleeps 4, $295/Night
You've found Hawaii’s Best Kept Secret! (And YES WE HAVE A LICENSE TO RENT SHORT-TERM! SEE BELOW) The cottage is adjacent to a whole mile of deserted beaches, where you’ll discover isolated sandy coves, driftwood and shells, and forested pastures filled with polo...
Ilikai 1001 Mountain & Waikiki City Views - King Bed, Sofa Bed
BEAUTIFUL WAIKIKI CITY/MOUNTAIN VIEWS! STEPS TO WAIKIKI BEACH. Memorable Meals from the Lanai. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life.The iconic Ilikai Suites are located at the gateway to Waikiki.Newly...
Makaha Hideaway by AvantStay | 10 Minutes to Beach
Kick back in the heart of Makaha Valley at Makaha Hideaway, a 3BR retreat that puts you 10 minutes from the beaches of Oahu. With a stunning view of tropical mountains from your backyard, this modern Hawaiian escape blends style, space, and a beautiful location to give...
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...
Turtle Bay Villa 310: Beachfront with Shared Pool, Spa & AC
Set within the 850-acre oceanfront community of Turtle Bay, Turtle Bay Villas 310 offers an elevated third-floor retreat where lush tropical views and resort-style comfort meet. This 1,538-square-foot villa accommodates up to eight guests across three beautifully...
Hale Ohana, Private, Oceanview home w/pool, Licensed TAT home
Set on the slopes of Koko Kai, this spacious, two-story, family-style home offers panoramic ocean views and breathtaking sunset over Diamond Head. Decorated with a touch of island decor, this villa is perfect for indoor/outdoor living. The large full kitchen, two living...
I comply with all Hawaii tax regulations. Hawaii Tax ID#: TA-158-127-3088-01Serenity......This peaceful retreat offers meticulous attention to detail and modern amenities on one acre of oceanfront property facing Mokoli'i Island (familiarly known as Chinaman's Hat) in...
Impeccable Penthouse - Ocean & Diamondhead Views
PANORAMIC OCEAN, DIAMOND HEAD & KAPOLANI PARK VIEWS. It's a première residential lifestyle ON THE GOLD COAST! A brief 15 minute breathtakingly beautiful walk to Waikiki’s famous beaches, shopping, dining and nightlife.This is not a tired old Waikiki hotel room with a...
Sweet Vintage Hawaiian Cottage and Guest House! Great deal in beautiful Lanikai!
At Old Hawaii Beach House and Guest Cottage in Lanikai, we extend to all our guests the old-fashioned Hawaiian Hospitality, and the famous Spirit of Aloha. Step back in time to the romance, the charm, that is truly 'Old Hawaii.' Tropical plants and flowers (seasonal) in...
Hale Kai Lily - Waterfront Hawaiian Getaway 10% discount for November 2025
This single-level waterfront, home is thoughtfully curated & designed. New AC in every room. Featuring a full kitchen, living room, and lanai as well as 4 bedrooms and 3 bathrooms. The property is fully furnished and boasts captivating marina views from all common areas...
Location, Location, Parking, Kitchen, Remodeled
W Hotel-inspired design in this newly remodeled and fully upgraded designer condo at a value price. Everything is new. Traverine floors throughout. The kitchen includes granite countertops tops Italian glass tile backsplash, and a dishwasher. The bath includes a vessel...