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.
Beautiful Makaha Valley, Best Beaches on Oahu, and Mountains for days.
Makaha can't be beat for those looking for uncrowded beaches, striking sunsets, hiking, and the incredible ease of real Hawaii. Our condo is outfitted with airy midcentury-modern styling and a hint of Hawaiiana as well as full frontal floor to ceiling glass rendering an...
Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates
Kuilima Collection #6 WESTWish You Were Here... on Oahu's famous North Shore at the world class Turtle Bay Golf and Tennis Resort. This spacious 2 bedroom, 2 Full Bath west side condo also has a bonus loft. Kitchens and bathrooms were remodeled in 2020. Other features...
Hidden Island Getaway
Hidden gem awaits your arrival. Newly renovated condo just minutes from one of Oahu’s many beautiful beaches, Makaha Beach. A welcoming family retreat 2 bedroom, 2 full bath, AC and full kitchen facility. Spacious living and dining providing ample space to plan your...
Direct Ocean View Luxury 2 beds/2 baths - Waikiki NO RESORT FEES! FREE WIFI
Beautiful unit overlooking the ocean and lagoon that you can enjoy from either of the two large lanais. This unit features new furniture (April 2019) including an Eastern King bed in the master bedroom, one queen bed and one twin bed in the second bedroom and a queen...
Extraordinary Listing on the Block!!! 2 Story Condo Renovated!
ALOHA! Kind Note: We’re excited to share that as of May 30th, 2025, we’ve installed a brand-new 36,000 BTU high-efficiency Mitsubishi split A/C unit in the loft area of the condo. This HVAC upgrade is part of our ongoing commitment to ensuring a cooler, more...
High Floor with Ocean View! Bedroom A/C, W/D, Wi-Fi, Pool, FREE Parking!
Fairway Villa #2502 – 2345 Ala Wai Blvd.Terrific views, contemporary/Hawaiian design, relaxing and close to everything! This fresh, quiet corner one-bedroom condo (635 interior sqft plus 76-sqft balcony/lanai with table and chairs) with bedroom A/C (great...
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...
Shimmering Ocean Views! A/C, Wi-Fi, Pool, Parking, Close to beach!
Waikiki Sunset #2512 – 229 Paoakalani Ave.Enjoy mesmerizing ocean vistas and views of Diamond Head and Kapiolani Park by day and colorful sunsets and city lights at night from this 25th floor condo with central AC (534 sq.ft. plus balcony/lanai), FREE parking and...
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...
Royal Garden at Waikiki - Premium Studio Condo
The Royal Garden at Waikiki is a luxurious and intimate condo-hotel. The moment you enter the lobby, you’re embraced by stunning Italian marble walls, columns and floors. Unlike the large, crowded hotels, this is a relaxed setting in a quieter area of Waikiki with 6...
Rare find! Actual 3 bedrooms/2 full bath 1500sf Ocean View corner unit apartment
This year we are celebrating having had over 300 five star online reviews!Minimum age requirement for principal renter: 30 years oldTop of the line 3 bdrm 2 full baths recently renovated corner unit with an ocean view in one of the most distinct buildings located in the...
1BR Condo with Beautiful Mountain Views and 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...
DESIGNER REMODELED CONDO AT ILIKAI MARINA
ON THE RENTAL MARKET AFTER A COMPLETE DESIGNER RENOVATION! BY FAR THE BEST LOOKING UNIT IN THE ENTIRE BUILDING!We're accepting reservations on an on-going basis. Superb Location next to the water! Completely remodeled with no expense spared condo boasts one of a kind...
Hilton Hawaiian Village Lagoon Tower, pristine beachfront resort, private lagoon
Please choose a Friday, Saturday, or Sunday check-in and enjoy a seven night stay.Thank you for your interest in booking with Dash Realty Group, Windermere Florida. Dash Realty Group is registered in Florida as a licensed Fla. Seller of Travel Ref. No. ST42435.Need a...
Guest suite, studio near the beach. 30 days minimum stay
Enjoy country style living in the North shore of Oahu. Located 5 minute walk from the beach. This place is perfect to work remotely. Near Surf spots. The area allows you to swim and snorkel year around in Waialua. In the evenings, enjoy a colorful sunset over the ocean....
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...
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...
Kai Aniani – Beachfront on Oahu's North Shore
Sea of Glass is an architecturally stunning beachfront home on the North Shore of Oahu, completely remodeled in 2018. The A-frame design is accentuated by windows that face Mount Ka’ala, the tallest mountain peak on the island to the south, and wall-to-wall sliding...
Turtle Bay Hale Lani - Kuilima Estates East
This beautiful, modern 1 bedroom w/loft bath and a half. Upgraded unit has new kitchen cabinets & appliances, ceramic tile floors and granite countertops. The extended living room has a large flat-screen TV, internet and WIFI, TV in master bedroom as well. Window a/c in...
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...
Waikiki Ocean, Lagoon & Marina Views! Short Walk to Beach, Restaurants & More
Ilikai Marina #1480 – 1765 Ala Moana Blvd.Incredible sweeping panoramic views of the Pacific Ocean, Duke Kahanamoku Lagoon/Beach, and marina; plus beautiful sunsets!Although there is NO pool onsite, it's just a quick stroll to Duke Kahanamoku Beach and Lagoon,...
Front Row Seat in this Luxury Condo, Ocean, Yacht Harbor, Fireworks, Restaurants
Check out our calendar for all the fun-filled dates available! Choose the 'You Found Paradise' luxury condo for a stay that's not just a vacation – it's an adventure! Why settle for the ordinary when you can embrace the extraordinary in our newly revamped condo?Step...
Ilikai Hotel - Perfect Waikiki Getaway! Overlooking The Mountains & City Lights!
If you're looking for an AMAZING deal in the most sought after location, look no further! This comfortable unit is located on the 12th floor of the Ilikai Hotel. Enjoy the tropical island breeze from your spacious lanai while taking in the city lights!KITCHEN-...
Gorgeous Ocean & Marina Views at The Ilikai! Close to Beach! Free Parking!
Ilikai #2039 – 1777 Ala Moana Blvd.You'll love the breathtaking ocean and marina views from this chic 20th floor studio at the Ilikai! Take in the blue skies, fabulous sunsets, and enjoy al fresco dining for 4 on your spacious private lanai as you relax on your...
Scandia 203 - Sleeps 6, Full Kitchen, Free Parking, and 1 Block to the Beach
Welcome to Mauka Makai, your gateway to the bustling and serene beauty of O‘ahu, nestled in Waikīkī, between the majestic Ko‘olau mountain range and the pristine Pacific Ocean. Recently renovated with upgraded amenities, appliances, and furniture, this exquisite...
Contemporary City View One Bedroom Condo at the Ilikai w/King Bed & AC!
Aloha and Mahalo from Waikiki! We are a short term vacation rental company, we are not part of the hotel. This gorgeous modern condo is newly renovated and newly furnished at the Ilikai. Spacious balcony with newly furnished exterior furnitures to enjoy morning coffee!...
Remodeled oasis in the heart of Waikiki! Min. from beach, shops, & restaurants!
Whether you seek relaxation, remote work vibes, ocean waves, or stunning sunsets, my cozy 1 bedroom space awaits. Experience the charm of my recently renovated dwelling, featuring one complimentary parking space. Revel in ample light, air, and full amenities. The living...
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...
Elegant Windsor Waikiki Condo
Surround yourself in luxurious, island-style furnishings with spectacular views of Diamond Head and the crystal blue waters of Waikiki. This elegant corner unit(1046 sq. ft.) offers 2 spacious master suites, 2 full baths and includes a fully equipped gourmet kitchen,...
@ Marbella Lane - Serene & Lovely MT + Ocean Views
Summary:Indulge in relaxation and rejuvenation as you take in the breathtaking ocean and mountain views from the living area windows of this peaceful and comfortable house. With convenient access to tropical beaches, surf spots, and hiking trails, your Hawaiian...
Hot Deal! Turtle Bay Villas 307 by Gather: Beachfront w/ Shared Pool, Spa, AC
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!Experience the ultimate Hawaiian getaway at Turtle Bay Villas by Gather. Whether you are looking for a romantic couples getaway or...
BEACHFRONT LEGAL PRINCESS CONDO-FREE PKG/WIFI-POOL, HOT TUB,TENNIS/PICKLE BALL 2
LEGAL VACATION RENTAL! AWESOME 180º UNOBSTRUCTED BEACH, OCEAN & SUNSET VIEWS! FREE PARKING IN GATED LOT and FREE INTERNET/HI-SPEED WiFi. NO RESORT FEE. POOL-HOT TUB-TENNIS-PICKLE BALL-PING PONG-BBQ**NO CENTRAL AC--HAS PORTABLE AC IN BEDROOM, BUT IT WILL NOT COOL OTHER...
Luxurious Guest home w/Swimming Pool Just Steps away from the Ocean/Beach.
Welcome to this exquisite Japanese-inspired retreat, a sanctuary of elegance and tranquility. This luxurious guest house seamlessly merges architectural sophistication with serene, peaceful vibes. Attached to the main residence yet offering complete privacy through its...
FULLY RENOVATED! AC, Washer/Dryer, FREE Parking & Wi-Fi, Pool, Walk to Beach!
Four Paddle #708 – 2140 Kuhio Ave.FULLY RENOVATED & REFURNISHED TOP TO BOTTOM IN 2021! Looking for the utmost in quality and comfort? This tastefully decorated, 1-bedroom condo (553 sqft plus lanai) with central AC is it! 2-person max.POOL CLOSURE NOTICE: The upper...
Million-Dollar Ocean Views! Steps from Beach! Full Kitchen
Waikiki Shore #1218 – 2161 Kalia Rd(LEGAL 30-Night Minimum Rental in the Resort Zone! ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)Unwind in this fresh, airy and spacious (932 square feet plus lanai) 12th-floor corner...
The Most Amazing Haleiwa Beach Front Condominium
The Best of the Best! Relaxation - Romance - Recreation.Aloha! We love our slice of paradise and take great care to provide our guests with a relaxing experience. We are especially proud that it is always neat and clean so that our guests can begin their vacation the...
Luxurious Ocean view 2-bed/2-bath condo with Pool, Wi-Fi, Parking.
Waikiki Beach Tower #1804 – 2470 Kalakaua Ave.You'll feel at home, right across the street from the best swimming and surfing beach — world famous Waikiki Beach! This beautiful 2-bedroom, 2-bath Waikiki Beach Tower condo with central air conditioning has 1092 square...
Cozy & Peaceful Oahu North Shore Oasis - Kahuku
A lovely, peaceful oasis for your wonderful North Shore getaway — “Hale Blue Aloha”🏝This end/corner unit offers nice privacy, away from the foot traffic of other units, just steps from the Fazio golf course 'back nine'. Simple, clean, and cozy, the unit has an...
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua Beach
Welcome to Palione Papalani – “Heavenly Sands”Just steps from world-famous Kailua Beach, this newly renovated 6-bedroom tropical estate offers the privacy, comfort, and amenities of a high-end resort — all to yourself. ?? Why You’ll Love It:Exclusive Location:...
Hale Makai at Diamond Head – Oceanfront Estate
We want to inform our valued guests that there is ongoing construction next door to Hale Makai at Diamond Head. This construction is expected to last into 2026. We apologize for any inconvenience and appreciate your understanding in this matter.This Diamond Head...
Warm Aloha Vibes: Mountain Views, Short Walk to Beach, and 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...
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...
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...
Beachfront View! A/C, Washer/Dryer, Wi-Fi, Sleeps 4!
Waikiki Shore #1010 – 2161 Kalia Rd.Waikiki Shore is the only condo in Waikiki where you can step directly from the building onto the sands of Waikiki Beach! This beachfront ocean-view condo (renovated in 2016) is a favorite with return guests! You'll feel right at...
Large private home with pool & ocean views - Inquire about dates!
Contact HVROAHU com for more detailsSpectacular 4 bed 2 bath home with private pool and breathtaking ocean and mountain views. Situated on the ridge in the highly desired area of Hawaii Kai. The main level includes a large open kitchen and dining area with plenty of...
Direct Oceanfront. Tranquility and Seclusion ~ Best Oceanfront Value!
30 DAY MINIMUM RENTALPrivate oceanfront house located on Oahu's West (Waianae) Coast near Makaha Surfing Beach. Enjoy the deep-blue ocean and great sunsets from the lanai and large grass lawn. Nap to the sound of the waves. The property fronts coral reefs and is five...
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...
Beachfront Cottage at Log Cabins
Our cottage is tucked away in a great location. Enjoy this private sanctuary on the bike path and within short walking distance to Pipeline or Shark's Cove. We have 3 bedrooms, two have one queen each, and the third has 2 twins. There is also a sofa for sleeping in the...
Ko Olina Beach Villas B204: Serene Ocean Views from Lanai
Discover the renewed charm of Ko Olina Beach Villas B204 by Gather, a stunning three-bedroom, three-bathroom villa on the second floor. Accommodating up to eight guests, this vacation rental blends luxury and tranquility, offering the perfect island retreat within the...
Private space in paradise
Nestled in the magical and untouched area of the fabled North Shore of Oahu, our charming private countryside beach cottage is a 5-minute walk to a private white sandy beach, surf, fishing and the best places to eat on the island. 1 bedroom, 1 full bathroom, sleeps 4 ....