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.
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...
ILIKAI 19th FL OCEAN VIEW - GREAT VALUE!
Beautiful Ocean & Lagoon Views from Bedroom, Living Room and Kitchen on the 19th floor of the iconic "Hawaii Five O" Ilikai Towers. Enjoy your Friday night Fireworks from the comfort of your own Lanai. The condo has a brand new quiet mini-split AC to regulate a perfect...
Stunning Ocean /Mountain Views in Luxury Million$ Homes w/ Ping Pong, Air Hockey
Feel the warmth of the Ohana spirit as you gather with family and friends in this stunning and yet affordable 4-bedroom, 2.5-bathroom paradise, nestled in the prestigious Mauna Olu Estates—“Cottages of Mauna Olu.” With breathtaking 360-degree views that stretch from the...
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...
North shore beachfront villa on Ke-iki beach
ALOHA!Welcome to our beachfront villa!This three bedroom home is located in a gated community fronting Ke-Iki beach, famous for its sand, surf and sunsets. It's also a great place to catch a glimpse of Humpback whales and spinner dolphins passing in the far-off waters....
Deluxe Garden View Waikiki Banyan, Free Parking
Waikiki Banyan Tower 1 Suite 708Deluxe City and Ocean View Condo at the Waikiki Banyan, Free Parking/Wi-FiThe pool and all associated amenities will be closed starting April 7, 2025, for an estimated duration of 10 to 14 months to accommodate the Recreation Deck...
Kahela - Paradise for Rent
Located just steps from the best part of Kailua Beach. The beach is a short walk through Kailua Beach Park where the waves are the most gentle, the sand is wide, and there are plenty of trees for shade, so you and the kids can play and relax at the beach all day. This...
Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua
Stay in comfort as long as you wish. 30 day minimum lease, shorter stud are of longer stays are welcome. Contact Us for Details and RatesHawaii Tax ID # available upon requestHale Pulelehua “The Butterfly House” has an open spacious Kailua feeling inside and out. The...
Beachfront, Peek-a-Boo Ocean Views, Washer/Dryer, A/C, Wi-Fi!
Waikiki Shore #308 – 2161 Kalia Rd.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 beach, pamper yourself with...
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, &...
Ocean view home office
Right by the Four Seasons at Ko Olina, the house is beautifully located inside the luxuriously built Kai Lani with an ocean view from the balcony and the master bedroom. Only minutes away from the beach at the Ko Olina lagoons, you will also have direct access to the Ko...
Cozy Oceanfront Home - Secluded Beach, North of Sunset Beach - Near Kawela Bay
Hawaii Tax I.D for both TAT & GET. No. 027-702-8864-01Our oceanfront home, Kawela Kai, is located on the North Shore of Oahu in between Sunset Beach and the Turtle Bay Resort. The stretch of beach where we are located is beautifully secluded and uncrowded. The beach is...
Kuilima Estates West 3 Bedroom
TMK (1)570010290042 Welcome to Kuilima Estates West. Location! Location! Location!Only steps to the grounds of the famous and newly renovated Turtle Bay Hotel on the North Shore. We are a Legal Vacation Rental.The condos are Surrounded by Two Beautifully manicured golf...
Resort-like, Beach-side Kailua Lanikai, Pool, AC, WiFi, Kayaks, 50% DISCOUNTS
We offer a solar-heated Pool, AC , WIFI, Kayaks, and up to 50% Discounts. This property is a 2 1/2 to 3 min walk from the sandy beach of Lanikai (the property marker shows the property location incorrectly).Walk through the entry gate, and find yourself in the middle of...
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...
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State...
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 #...
Poolside Paradise at Ko Olina : Elegance Spacious 2BR OT512 w/ Gym & Pool Access
Luxurious Condo - 2 bedroom(1king,2twin) + Pull out sofabed /2 bath 1parking Sleeps 6A luxurious room at Ko Olina Beach Villas. : Poolside location with easy access to the lagoon and resort amenities. - 5th floor of the Ocean Tower facing the pool and ocean .At 1,319...
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...
Ko Olina Beach Villas O224 by Gather: Luxe Villa w/ Pool & Oceanviews from Lanai
Ko Olina Beach Villas O224 offers an elegant sanctuary amid the lush landscapes of Kapolei, HI. Located in a private gated resort community, this 2-bedroom, 2-bath villa blends indoor comfort with outdoor beauty, featuring an inviting flow to a spacious lanai with...
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!
TA-166-694-5024-01 STR Permit # 2211-CCH-0303, TMK 1260230500039Enjoy the ocean with gorgeous sunsets day after day. Fun shopping, great restaurants & entertainment all around you!This studio is the perfect choice for your Hawaiian holiday! With comfortable...
Fully Renovated 2BR/2BA Near Waikiki 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...
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...
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...
Hale Kalea - Oceanfront Vacation Rental on the North Shore of Oahu
Oceanfront Paradise on Oahu’s North Shore!Escape the city and experience the legendary North Shore of Oahu at its finest—where sunsets, surf, and the spirit of “Real Hawaii” come alive. Perfectly situated on the iconic stretch between Sunset Beach and Pipeline, this...
Villa B207 Private location closest to the beach, Ko Olina 3-bed beach villa!
This privately located beach tower villa 207 has no neighbors on either side and offers beautiful ocean and lagoon pool views! Located on 2nd level in the preferred Beach Tower building, this Villa is the closest 3 bedroom to the beach! This villa has Hawaiian touches...
Open and relaxing vacation home with breathtaking panoramic ocean view
This home is perfect for the savvy, discerning traveler who prefers comfort, convenience, cleanliness, spaciousness, and spectacular views. Discover the hidden gems of an affluent neighborhood with gorgeous views, privacy, and lots of aloha.This renovated, fully...
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...
Waikiki Beach ocean view studio with pool access right on the white sand beach.
Enjoy spectacular Ocean views of the white sand beach and sparkling turquoise waters from inside this condo and from your lanai. Step out of the elevator and straight on to the warm sands of Waikiki Beach. You can not find a better location! One of the closest studio's...
Luxury 2-Bed/2-Bath Corner Waikiki Shore Condo w/ Ocean Views! FREE Parking!
Waikiki Shore #918 – 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! This beautiful Balinese-inspired beachfront condo (renovated 2014) is sure to be your new favorite vacation spot!...
Vacation In Paradise At Makaha Area in a Legal NUC
Come to Paradise on Earth at the Hawaiian Princess located in the dry, sunny Makaha Area in West Oahu. The condo is on a secluded 1/3 mile pristine white sand beach overlooking the gorgeous Turtle Cove. Celebrate a special occasion, romantic getaway or just come to...
Beautiful, Tropical Vacation Rental in Keauhou! STVR-19-366304.
This beautiful tropical vacation rental in the Keauhou Resort area of Kailua-Kona, HI is only a block away from stunning Keauhou Bay and across the street from the Kona Country Clubs wonderful ocean golf course. Walk to Keauhou Bay and jump on the Fairwind snorkel...
37FL-Elegant Waikiki King Studio with Fabulous Views
Enjoy breathtaking views of the ocean, Diamond Head, golf course, and city skyline from this beautifully renovated condo. Immaculate and tastefully furnished, the space offers modern comfort with a quiet split A/C system for cool, relaxing stays.🌴 Prime Location – Just...
BEAUTIFUL HOUSE WITH 7/AC,BED ROOMS AND OCEAN VIEW
Location: Hauula, North Oahu, Oahu, Hawaii, USA (LOCATED TWO MILES EAST OF THE POLYNESIAN CULTURAL CENTRE) Accommodations: House, 7 air-condition Bedrooms + Convertible bed(s), 3 full Baths (Sleeps 9-18)Keywords: 7/AC Bed Rooms HouseFIVE STAR EXPERIENCE FOR A FRACTION...
Spacious and Renovated Waikiki Condo With Full Kitchen and Ocean Views
Renovated, clean and spacious studio in Waikiki. Unit is on 38th floor of the Hawaiian Monarch Hotel/Condo building and comes with queen bed, full kitchen, full bath and amazing ocean, canal, diamond head and mountain range views. Walk to Waikiki beach, Waikiki strip,...
Holiday Sale! Turtle Bay Villas 201 by Gather: Beachfront w/ Shared Pool, Spa/AC
Turtle Bay Villas 201 offers one of the most coveted locations on Oahu’s legendary North Shore—just steps from the beach, the Turtle Bay Ocean Villas pool, and miles of shoreline trails. This second-level, recently refreshed 4-bedroom, 3-bath villa is the closest 4BR...
Ko Olina Beach Villas O1004: Oceanfront Penthouse Escape w/Pool & Golf Views
Ko Olina Beach Villas O1004 offers an exquisite retreat where luxury meets island life, perfectly situated in Kapolei, HI. This two-bedroom, two-bath penthouse villa spans 1,187 square feet and invites you to unwind on its expansive lanai, where gentle breezes and ocean...
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,...
Tastefully remodeled Apt w/ Mountain 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...
Marriott Ko Olina Beach Club - Studio Ocean View - Includes Tax and Parking.
The Marriott Ko Olina Beach Club Resort offers daily and mid-week availability. ( 3- 5 Night Minimum ) Rates are based on weekly stays in USD and will vary by week, view and season / holiday. Daily rates will increase for 3 - 7 night stays.Marriott owner services is...
Paradise Found at Hawaiian Princess, Makaha!
Aloha! If you're looking for an authentic Hawaiian experience, stunning beaches, local eateries, and a peaceful atmosphere far from the Waikiki hustle and bustle, you've found it! This one-bedroom, one-bath condo at Hawaiian Princess in Makaha, on Oahu’s beautiful...
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...
Amazing ocean views from this 11th floor villa!
This elegant Villa in the Ocean Tower overlooks the Pacific Ocean, sandy beach Lagoons, and the pools at KoOlina's premier residential resort community, The Beach Villas. Our resort sits aside the 2nd lagoon beach, next to the world class Disney Aulani Hotel and...
New Remodel, Pool, Beach Access, A/C - Kuilima Estates West
Relax and unwind with your family in modern luxury. We’re excited to share with you our newly renovated oceanside condo. Nestled perfectly between the North Shore of Oahu’s world class surfing destinations and world famous golf courses - you’ll never be without endless...
Luxury Suite w/ Ocean View in Waikiki + 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...
Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach
Escape to Hale Aloha by Gather, a serene four-bedroom, two-bathroom waterfront retreat nestled at the end of a peaceful Kailua cul-de-sac. This 1,810-square-foot sanctuary sits on an expansive 12,000-square-foot lot, blending island charm, privacy, and modern comfort...
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,...
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...
Waikiki Spacious One Bedroom Ocean View
Fabulous ocean view condo on Waikiki beach with one bedroom, one bath, a tiki bar lanai for watching the sunset & surfers, & a parking space. Large flat screen TV, free internet, secured residential building, salt water pool & spa, across Kalakaua Ave. from the beach....
Location, Location, Location
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...