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.
Kalae Villa ~5 min walk to Beach, A/C, New Remodel
Kalae Villas are an ideal gathering place for larger groups with easy access to a sandy beach. This listing represents several comparable homes located along the Windward shore, from Laie to Kaneohe. All homes feature a matching layout, number of bedrooms and bathrooms,...
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...
Renovated Ocean View Suite, 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...
Epic View w/Gourmet Kitchen–Waikīkī Shore #1100
Castle Waikīkī Shore unit #1100: Elevate your Waikīkī experience within 1,190sf of pure paradise! Our largest air-conditioned retreat indulges with an open design kitchen and living area, where floor-to-ceiling windows unfold to a beautiful panorama spanning the...
King bed & Futon, Waikiki Studio with a view, kitchen & Free parking
Legal vacation Rental: 364 Seaside Ave.A beautiful 17th floor King bed Studio in the heart of Waikiki. Cook from home with ease and avoid paying hefty parking charges with your own dedicated parking spot included free.Stunning bathroom with oversized walk-in shower,...
~Waikiki~ LOWEST RATES IN AREA ~ 1 Bedroom ~ Fully Furn ~ Blocks to Beach ~
We offer our Hale to you to enjoy the benefits of staying in one of the largest Apts. in our surrounding location, right in the Heart of Waikiki.Our large open floor plan is fabulous featuring a living/dining room combo. All 1 Bedroom apts. have a private lanai for your...
Makaha Beach Front Luxury Bamboo Compound Resort
Take the country road out to West Makaha's Crystal Blue Waters. Feel the ocean breezes where Bethany Hamilton's soul surfer movie was filmed in the waves in front of our very unique new beachfront luxury bamboo compound resort with over 150 feet of sandy beach!! - all...
Private Waterfront House AC & Fast Wi-Fi 30 Day
This house is all about being right on the water. A seawall provides protection from waves at high tide. A North Shore Beach House with the comforts of a nice home ideal for long term stays. Local pickle ball played right down the street. 30 Day Minimum ContractIncluded...
Hale Kai | Pampered Ko Olina Villa
Summary:Welcome to Hale Kai in Ko Olina! If you enjoy panoramic ocean views and tiki-lined pathways to white sand beaches, Ko Olina Kai is the paradise for you. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Once you're finally able to...
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...
Majestic Tropical Ko'olau Mountain views! Washlet!
Waikiki Sunset #2807 – 229 Paoakalani Ave.Savor fabulous mountain views by day and sparkling city lights at night from this 28th floor, one-bedroom condo (546 sqft plus access to lanai from bedroom with small table and chairs). Central AC, free Wi-Fi, Washlet, and 1...
Luxury Oceanside/Beauty, FREE Parking/Wi-Fi, 2/2, AC, W/D, Washlet, Sleeps 6
Ilikai #744 – 1777 Ala Moana Blvd.Enjoy luxurious high-end ocean-view living in this beautiful 2014 remodeled condo at the ILIKAI, the iconic Hawaiian apartment/hotel made famous by the TV show Hawaii Five-O. This 7th floor corner unit boasts magnificent views of the...
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...
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...
Waipuna Hale: Oceanfront Cottage w/Panoramic Views, Yard, & Private Beach Access
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Waipuna Cottage, a charming...
Ilikai Hotel Renovated Condo Steps Away From Beach w/Free WiFi & Full Kitchen
Book with confidence! This property is professionally managed by Ali'i Beach Rentals.ENHANCED PROTOCOLS : We have revised our protocols to include contactless check-in & check-out, professional EPA approved non-toxic undetectable antimicrobial electrostatic spray...
Turtle Bay - Relax In Paradise - Kuilima Estates West
Aloha ! Welcome to my condo located at 57-101 Kuilima Dr. Kahuku Hawaii 96712. My condo is clean, well maintained, and comes with many amenities . Some amenities are Tennis rackets, bodyboards, snorkel and mask sets , beach towels, beach chairs, and more. Full access to...
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...
Hale Kai | Ko Olina | Villa w/ Ocean Views!
Summary:Welcome to Hale Kai 2 in Ko Olina! Immerse yourself in this coastal getaway, where colorful landscaping and shimmering lagoon pools await. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Whether you're unwinding in the steamy...
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...
Comfortable Condo on Turtle Bay Golf Course Sleeps 5 - Kuilima Estates West
Located on the North Shore of Oahu at Turtle Bay, our condo sits on the Championship Fazio Golf Course. There are multiple walking trails and paths that lead to quiet secluded beaches or world-famous beaches such as Sunset Beach, Waimea Bay, and Pipeline. A large pool...
Ko Olina Beach Villa O1404 by Gather: Modern Penthouse w/ Panoramic Ocean Views
Welcome to Ko Olina Beach Villa O1404 by Gather, a stunning 14th-floor penthouse in Kapolei, Hawaii, where elegance meets comfort. This 2-bedroom, 2-bathroom villa accommodates up to six guests, offering a luxurious escape with breathtaking 180-degree ocean views and...
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
Charming Cottage in beautiful Lanikai that has been totally renovated in 2021. Everything in the Cottage is new including the furnishings! Short walk to the beach. Enjoy the comforts of home with an efficient kitchen and own washer and dryer. Large lanai to extend the...
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...
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...
Charming Condo Steps from 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...
Ocean View from Lanais - Walk to Waikiki Beach
Your home away from home in paradise, featuring views of Waikiki Beach from the 2 lanais! 925 sf, perfect for families and groups - sleeps up to 6 people. 2 bedrooms, 2 full baths. Located just two blocks from Waikiki Beach, with endless dining, shopping, and activities...
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...
Ilikai 1510 Great Views 2 Bed Room Corner Unit Ocean / Marina Views
FINEST OCEAN / MARINA VIEWS / CORNER UNIT - WAIKIKI BEACH. 2 bedroom, 2 full bathrooms, 2 120 sq. ft lanais, 1,000 interior sq. ft. Walking distance to parks, shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life.This condo is in the "10"...
Centrally Located Vacation Rental in Waikiki!
Make this nifty Honolulu vacation rental the backdrop to your family’s relaxing getaway with its community pool, well-equipped kitchen, Smart cable TV, and fantastic location! Look forward to being within walking distance of Waikiki’s entertainment hub, from...
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...
Waikiki Cozy Apartment, 2 Bedrooms, FREE parking, Sleep 6
Aloha 🌺 Make your stay memorable at our island lifestyle legal vacation rental! Newly renovated 2 bedrooms with pool view, prime location in Waikiki, Honolulu, near the beaches, canal, golf course, Ala Moana & Royal Hawaiian Shopping Center, International...
Spacious Ilikai Studio with one FREE parking/Wi-Fi and Marina/Ocean Views!
Ilikai #341 – 1777 Ala Moana Blvd.For those who prefer a lower floor and still enjoy great marina and Pacific Ocean views, you'll love this inviting 3rd floor studio at the Ilikai, the Waikiki landmark made world-famous by Hawaii Five-O! Enjoy your morning coffee or a...
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...
Wake up in paradise with a touch of Hawaiian rainbow
Wake up in paradise in a one bedroom apartment just a stone throw away from the Waikiki beach.Waikiki park Heights is located just 2 blocks away from the beach, international market place , the most famous HY's steak house in Honolulu and a lot of good Hawaiian style...
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...
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!...
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:...
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...
Free parking, 2 weekly towel changes, F/Kitchen, GYM, AC, WiFi, pool, Pool/ping
This deluxe studio is in the Royal Kuhio building. We manage 39 units and are offering a rare experience opportunity to stay in one of our units. Each unit has a full kitchen, including a box of chocolate macadamia nuts and 4 bottles of water to WELCOME you to our...
Unobstructed Diamond Head and Ocean Views!
Waikiki Banyan #3511-T1 – 201 Ohua Ave.Unobstructed panoramic views of Diamond Head, the Pacific Ocean, and the Gold Coast from this 35th floor unit! Modern and contemporary, this air-conditioned condo has tasteful Hawaiian touches, 533 sq.ft. plus lanai with table...
WaikikiLux 509 Waikiki
Our side by side units are located right in the heart of Waikiki where almost everything you desire is within walking distance, great for families or business associates traveling together. Clean updated fully equipped units. Full kitchens, linens, bath/beach towels,...
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...
Waikiki Fully Furnished w/pool - walk to beach!
Waikiki Fully Furnished Ready-to-rent Condo.Centrally located in the heart of Waikiki, Honolulu. Minutes away from the prime strip of Waikiki Beach, Waikiki Market, Waikiki International Market place, Honolulu Zoo, Kapiolani Park, Waikiki Shell, shops, restaurants, bus...
Heavenly Hale Best Licensed Vacation rental - walk to beach!
Garage. Recently renovated and beautifully, tastefully furnished. Light & Bright. Full kitchen with high end appliances, Ohia hardwood floors, breathtaking views from every window. No pets firm. Living room, TV room, large kitchen, table, outdoor dining room, wrap...
Stunning Ocean and Diamond Head View Luxury Condo
This is a beautifully appointed 2 bedroom 2 bath condo with approximately 1170 square feet of living space and 1 parking stall on the convenient lobby level. This unit is on the 41st floor (one floor below the penthouse) of one of Waikiki's best buildings and has...
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...
Summer special! Tradewinds Habiscus; Free Internet and Assigned Parking, AC
CLOSE TO ZOO. FREE ASSIGNED PARKING!I AM FLEXIBLE WITH CHECK IN AND CHECK OUT TIMES IF I DONT HAVE BACK TO BACK BOOKINGS. I use this Condo when I want to spend time in Waikiki so I want it nice! Great location away from the hustle and bustle of people, cars and buses....
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...
Hawaiian Escape with all the Amenities
Located in one of the newest and most sought after resorts in Hawaii, this beautiful ground floor 2-bedroom, two full bath upgraded condominium with lanai and garage parking is right in the heart of the gated Ko Olina Kai golf course community. It is a short walk or...