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.
The Pineapple Place, A gorgeous 9th floor Waikiki Apartment + Pool & Spa
Be close to the beach with the whole family at this stylish 1 bedroom central Waikiki apartment.When it comes to top locations with great views, The Pacific Monarch really stands out.This modern & stylish 1 bedroom apartment goes above & beyond usual...
Beachfront Penthouse - Newly Renovated!!!
Immaculate, newly renovated, ocean front condo- relaxing retreat for couples!This beautiful newly renovated penthouse unit is a tropical paradise that offers a tranquil and perfect Hawaii escape. Designed and furnished by Archipelago Hawaii, one of Hawaii's top interior...
Absolutely Beautiful Ocean Front Condo! Sleeps 4!!!!!
Just 45 minutes from the Honolulu International Airport, you will find one of the best kept vacation destination secrets....The Hawaiian Princess. Come relax in this beautiful modern, just remodeled, oceanfront condo.This 1 bedroom has queen tempurpedic bed, sofa pull...
Resort Living Off the Beaten Path
***WE ARE ON OAHU, AND CONTINUE TO WELCOME TOURISM***The fabled North Shore of Hawaii is a hidden jewel off the beaten path. Enjoy wonderful dinners watching the sunset on your peaceful breezy lanai.This spacious condo has 1 bedroom, 1 bath, plus loft and is fully air...
Diamond Head View Rare Condo at the Waikiki Banyan by the Beach with Parking
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.09/18/24: BUILDING NOTICE: Please be advise the building working on elevators, there will be 3 working elevators for each tower.03/24/25:...
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...
Bright, clean, airy Rocky Point Beach 1 bedroom loft. Steps to beach & bike path
This Beautiful one bedroom loft is located between pipeline beach and sunset beach at the famous surf spot 'Rocky Point'. We are just 4 houses from the the beach. The North shore bike path is just steps away. There are multiple gourmet food trucks that park all along...
1BR Ocean View Condo with King Bed & 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...
Waikiki Luxury Penthouse 30 Days Rental
A luxury penthouse in a new secure boutique building in Waikiki featuring 17' ceilings, skylight, wood floors, granite counter tops, high-end appliances, wine refrigerator, designer furniture, fine artwork, spectacular marble bathrooms, jacuzzi bathtub, filtered water...
Hale Aina ~ Home of the Land
Spacious 1-Bedroom, 2-Bath Plus Loft at Ku'ilima Estates – Short distance to The Ritz-Carlton at Turtle BayExperience island living at its finest in this contemporary, art-filled 1-bedroom, 2-bathroom loft unit at Ku'ilima Estates, located just minutes from the...
BEACH HOUSE on Scenic Makaha Beach with Free High Speed WIFI and Onsite Parking
Working from home? Why??? When you can work from Paradise.Now accepting 30-day reservations. You will find it less crowded, a little unexpected, and truly delightful. The vibe here is RETRO and CHILL, so let the good times roll. Please message us for details as we do...
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....
North shore living! Walking distance to Hale’iwa town. Private lanai, AC, WiFi.
30 day minimum! Welcome to north shore living! This comfortable, vibrant beach house upstairs unit has everything you need plus more for an amazing vacation. Enjoy ice cold AC after a long day at the beach, a fun, private lanai with a hammock overlooking beautiful views...
Modern Ocean View Studio - Waikiki Paradise!
Thoughtfully appointed studio with modern decor. Fully renovated in February 2022! Includes FREE high speed Wi-Fi, cable TV, and various TV apps for streaming services.Check in and out at your convenience with a lock box. Check in after 3pm and check out before 11am....
Luxury Ko Olina - Spacious 3BR - BT304 Beach Paradise Ocean Views
Luxurious 3-Bedroom Beach Tower Villa | Sleeps 6-8 | Steps from the Lagoon Ko Olina Beach Villas | Kapolei, HawaiiNewly Upgraded (Oct 2024): Washer, dryer, and dishwasher!Villa Features:Spacious 3-bedroom, 2.5-bath villa (1 King, 1 Queen, 2 Twin beds, + 1 sofa...
Turtle Bay Villa 108: Ground Level 3BR Condo w/ Shared Pool
Please Note: Access to resort amenities is not included, however, the condo complex has its own pool, grills and is just steps to the beach!Prepare to settle into island time a little easier with the unparalleled accommodations and amenities that await you at Turtle Bay...
Large Oceanfront House on a Secret Beach with Spacious Yard and Amazing Views
Beautiful Country Beach House in Laie, Hawaii. Our Spacious property has all you need for your extended family retreat. Located on a gated oceanfront property our guests enjoy privacy and seclusion. The highlight of our property is its oceanfront location. We have...
Beautiful Waikiki Ocean/Sunset View! Pool, Kitchen
Ilikai #1629 – 1777 Ala Moana Blvd.The beautiful marina and ocean views from this contemporary 16th floor studio at The Ilikai, made famous in the opening credits of the original Hawaii Five-O, will remind you that you're on vacation in one of the most beautiful...
HONU KAI HIDEAWAY
Honu Kai Hideaway is like a treehouse with views of ocean, golf course and mountains. We are nestled among the trees and lush landscaping of the spectacular Turtle Bay Resort, an 880 acre tropical paradise. Our Hideaway is the perfect blend of tropical seclusion amidst...
5 minutes from Waikiki Beach, Ocean Views, Free Parking, Wifi & Cable TV
Waikiki is Hawaii's number one tourist destination. The penthouse condo has ocean views and is steps away from Waikiki Beach and has a partial view of the iconic slopes of Diamond Head Crater. It is a short walk to the Hilton Hawaiian Village, Hale Koa and Royal...
Turtle Bay Oceanview Beachfront 3 Bedroom Villa #314
TMK #: 570010130053, GE-124-431-5648-01, TA-124-431-5648-01, Permit#: 2301-CCH-1025See other host fees compared to ours3 Bedroom Top Floor Ocean Villa at Turtle Bay Resort with Ocean and Pool ViewsPrime beach front and ocean front location. Excellent natural cross...
Summer Reduced! Gorgeous Ocean and Pool View Villa O503!
Ocean Tower villa 503 has a gorgeous view over the pool to the ocean! This villa offers Hawaiian touches and high-end furnishings throughout. This villa is great for families or couples looking to get away! Photographs are of the actual villa.- 1,575 sq ft of living...
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....
Famous Ilikai Ocean View Luxury Condo! NO RESORT FEES! FREE WIFI
This 500 s.f large Ililai studio offers a cozy retreat for guests. With a comfortable king bed and a pull out queen sized sleeper couch make 4 people sleep comfortable. There are open full kitchen with granite counter tops and a granite shower bathroom. Split AC and...
Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East
Panoramic Arnold Palmer golf course views and gorgeous mountains surrounding the Turtle Bay Resort welcome you at the Kuilima Collection | 101 East The set up:1 BEDROOM | Super cozy, plush, pillow-top Queen sized bed with A/C and smart TV. Ample closet space and...
Cozy Beach front condo in Makaha
INCREDIBLE BEACH FRONT CONDO!NUC No: 90/TVU-0206One of the best accommodation bargains on Oahu!Makaha Cabanas are located on the best white sand beach on the sunny side of the island. You have a gorgeous 180 degree ocean view with turtle, dolphin and whale watching from...
Haleiwa Waterfront House
LEGALLY LICENSED VACATION RENTALLocation, location, location! This lovely home is perfectly situated on a beautiful white sandy beach, at the end of a quit cull de sac. You will find all the space and privacy that one needs to enjoy a nice peaceful holiday. Historic...
Mountain and Golf Course Views! Washer/dryer, A/C, FREE Wi-Fi and Parking!
Canal House #2007 – 2611 Ala Wai Blvd(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)With spectacular views of the Ala Wai Canal, golf course, and Ko’olau Mountains, this 598 sq. ft. one-bedroom condo with AC has a 43 sqft lanai and is just a...
Marriott Ko Olina Beach Club - Studio - Includes Tax, Parking and Amenities
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...
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...
High Floor with GREAT Ocean Views! A/C, Washer/Dryer, FREE Parking and Wi-Fi!
Waikiki Skytower #2804 – 2410 Cleghorn St.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Enjoy magnificent Pacific Ocean views from this contemporary, updated high-floor, one-bedroom condo (585sf plus 90sf lanai with table & chairs)! With only 4...
NORTH SHORE OCEAN FRONT - 30 day rental TA 044773171201
Welcome to Hale Aloha. Please inquire about staying at our property! Our home was recently remodeled in 2016 with new everything including central AC and has a detached enclosed garage. This is the first time it has been available for rent and is in excellent condition...
Spacious 2 bedroom, 2 bath, 1 free parking with world famous ocean view!!
Spacious 2 bedroom, 2 bath, 1 FREE parking unit with world famous ocean view!!!Be on vacation every day!! Direct Ocean & Sunset views of Waikiki Beach!!! Swim and Surf directly across the street of just watch the Surfers go by from the lanai! Spacious 2 bedroom, 2 bath...
Hot Deal! Turtle Bay Villas 205 by Gather: Beachfront w/ Shared Pool, Spa, Lanai
Please Note: Access to resort amenities is not included, however, the condo complex has its own pool, grills and is just steps to the beach!Prepare to settle into island time a little easier with the unparalleled accommodations and amenities that await you at Turtle Bay...
Ilikai 2122 Deluxe Ocean, Lagoon Views Kg Bed, Sofa Bed, Parking Included
STUNNING OCEAN & Lagoon VIEWS! STEPS TO WAIKIKI BEACH. SPECIAL - Includes Parking Stall. Memorable Meals & Views from the Lanai. , shops, buses, rental cars, parks & Waikiki night life.Beautiful remodel. Fully equipped and very clean. Parking spot included. AC, cable,...
Luxury Oasis Resort Villa
This newly renovated luxurious Villa is nestled in the quiet neighborhood of Ko Olina Hillside. This Villa has 3 bedrooms/1 sleep sofa and can sleep up to eight guests. Choose to spend your days on the Ko Olina Championship golf course or at one of the 4 lagoons located...
Townhome at Kuilima Estates at Turtle Bay
Welcome to this spacious second story townhome at Kuilima Estates at Turtle Bay. This condo is located on the eastern side of Kuilima Estates, making this condo one of the closest units to the Turtle Bay beach. .With a completely updated interior, guests enter into the...
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...
Elevate Your Hawaiian Getaway at Lagoon Tower by Hilton – 2 Bd. Ocean View
Nestled within the stunning Hilton Hawaiian Village® Waikiki Beach Resort, the Lagoon Tower delivers a vibrant vacation experience that’s both luxurious and family-friendly. With breathtaking ocean views, spacious accommodations, and endless activities, this is the...
Near Waikiki Beach, Spacious Studio With Full Kitchen!
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. The project is expected to be completed by mid-December.This condo is situated on the 13th floor of the...
Aloha Suite Near the Sea II, 3 Block Walk to Beach
TA 028 872 2944 01, STR Permit # 2211-CCH-0281 expires 11/22/25, TMK 260230500087Convenience & Location! Just 3 SHORT BLOCKS TO WAIKIKI BEACH! Enjoy the ocean with gorgeous sunsets day after day. Fun shopping, great restaurants & entertainment all around you!This studio...
Plumeria Tree Hale - Golf Course View - Sleeps 4
Welcome to Plumeria Tree Hale!! Part of the Kuilima Estates East community, this tastefully designed unit comes with 1 bedroom, 1 bathroom and offers 785 interior square feet of space for your enjoyment. The property was named Plumeria Tree Hale (house) for the...
Pacific Monarch Top Floor Condo with Ocean, Diamond Head and Mountain Views!
Step into your own slice of paradise in this beautifully appointed 23rd-floor retreat at Pacific Monarch. Designed for those who crave both luxury and the relaxed spirit of island living, this one-bedroom escape offers a serene atmosphere with stunning views of...
Luxury Ilikai Ocean View Studio! *NO RESORT FEES! FREE WIFI*
Luxury unit with amazing lagoon/ocean/beach views. Open kitchen, granite countertops, granite bathrooms, and so much more!This unit has a comfortable king bed and queen sized sofa bed, a free wireless work desk, and a 120 s.f of lanai to enjoy the ocean breeze and relax...
New Listing: Spacious Suite for 4x with panoramic ocean view
Our Tropical Treasure is situated at a cool 1300' elevation with a "million dollar view" over looking the ocean. The climate is perfect all year around.This 1-bedroom studio is a sanctuary after a day at the beach or exploring other parts of the island. This...
Comfortable 2 Bedroom, 2 Bath, Free Parking, Walk to Beach
Recently renovated 2 bedroom, with 2 bath and one free assigned parking.24th floor corner unit with views of the Ala Wai Canal and golf course from thelanai. Fully equipped kitchen, with dishwasher, coffeemaker, toaster and rice cooker.Washer and dryer included. Big...
Beautiful 1BR, Steps to 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...
Ocean View Upgraded Waikiki Banyan
Summary:Unit Summary:Waikiki Banyan (Tower 1) 34th Floor offers unobstructed Diamond Head and Ocean views! Also overlooking Kapiolani Park. This is a clean and comfortable furnished unit.Tower 1 and the views from the 34th floor makes this one of the best and preferred...
Elegant Condo! Best Location - Exceptional! *Legal Rental NUC No. 90/TVU-0562
Come to the country and escape the crowds! Enjoy the fresh clean air on the North Shore! This unit is situated in a wonderfully convenient location on the West side of the Kuilima Estates complex. The bathroom was just renovated with a brand-new standup shower and fresh...
Breathtaking Ocean View 1 BR Condo 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...