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.
Hale Kai - Large Enclosed Lanai - Sleeps 2
Hale Kai - Spacious Enclosed Lanai - Sleeps 2Welcome to Hale Kai, your “Home by the Sea” in the charming Kuilima Estates East community. This beautifully designed island-style retreat offers 875 square feet of living space, including a large enclosed lanai, perfect for...
5-star and rave reviews. Amazing views. Newly furnished. Specials for April/May!
SPECIAL RATES for the 2025 Fall Season! Relax in what feels like your open-air home in paradise! Stunning views. Savor the outside air and breezes on your lanai. Superbly maintained. Consistent rave reviews (for years as we are original proud owners).Discounts for stays...
Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath
Minimum rental period of 30 days, Rental included Electric, Water, Cable WiFi Clean the yard twice a month and clean the swimming pool every Tuesday and FridayUpscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the...
Kai Lani 14B by Gather: 3BR Resort Townhome w/ Pool & Spa
Welcome to Kai Lani 14B by Gather, your luxurious Hawaiian retreat in the exclusive Kai Lani community of Ko Olina Resort. Nestled on O‘ahu’s sunny west coast, this single-level 3-bedroom, 2-bath townhouse blends modern comfort with island serenity—perfect for families,...
KoOlina Beach Club Oceanfront Resort
Please choose a Friday through Sunday check-in for a 7 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.Rates are set for...
Executive Center Studio with Kitchenette, secure building pool, FREE PARKING
Updated downtown studio with (Free Parking a $50.00 Value per night can go in and out no charge/ dedicated parking stall few feet away from elevator ) located in the Aston Executive Centre. Enjoy hotel amenities including 24 hour security, pool, hot tub, on site laundry...
Welcome to Park Lane, an exquisite residential resort community conveniently located in the heart of Honolulu (direct elevator access to the world-class Ala Moana Shopping Center and across the street from Ala Moana Beach Park). The elegantly designed 3 bedroom, 3.5...
Beachfront Paradise North Shore, 4BD, King Beds, AC, Parking.
Escape to paradise in this newly remodeled beach house with panoramic ocean views. Step from the back lanai directly onto the sand. In the summer months, enjoy a private stretch of beach right out front, or take a few steps to the right to a larger, semi-private beach....
Marriott's Ko Olina Beach Club - Luxury 2 Bedroom Villa
Marriott’s Ko Olina Beach Club is situated on the beautiful Western shore of Oahu, where waterfalls and fountains welcome you as you drive under the port- cochere. Just 30 minutes from Honolulu, this beach front oasis is secluded and peaceful. Surrounded by seven...
Lanikai Breeze – Contemporary Comfort Steps from the Shore
Just steps from world-famous Lanikai Beach, Lanikai Breeze by Gather offers the ultimate blend of modern luxury and relaxed coastal charm. Built in 2017 and beautifully furnished by local designer Lotus Home Staging, this 5-bedroom, 4.5-bath home was crafted for...
Condo 1 block from Waikiki Beach
This is my timeshare. Please do not try to book this directly. Send me a request for the dates you are looking for so I can check with the timeshare location for availability. This property is a 2 minute walk to the beach. Set moments from Waikiki Beach and offering...
Primo View Beach Condo w/Washer/Dryer, Free WiFi, Kitchen – Waikīkī Shore #716
This deluxe one-bedroom one-bathroom suite offers wonderful views of Waikiki beach and Pacific Ocean from the furnished lanai. This unit has a full-size kitchen with all the appliances to make wonderful meals in your home away from home. The suite is also furnished with...
Located just a block from Waikiki Beach and surrounded by top-tier hotels, this gorgeous penthouse condo offers the style and comfort of a luxury hotel with the added benefits of 1700+ square feet of living space, a large well-appointed kitchen, extra-large private...
Ko Olina Beach Villas O1006: Luxe Penthouse w/Pool, Golf, & Ocean Views
Welcome to Ko Olina Beach Villas O1006 by Gather, a luxurious two-bedroom, two-bathroom penthouse on the tenth floor of the exclusive Ocean Tower. Designed for up to six guests, this elegant villa offers panoramic ocean views, serene vistas of the resort pools and koi...
New Aloha Ilikai 1Free Parking<br>(1777 Ala Moana BLVD)
ALOHA! Fully Renovated in June of 2025 / 1 free parking(There is a top-quality water purifier inside the unit, so there is no need to buy bottled water.)Perfect for couples, families, solo travelers, or business stayWe offer the ultimate Waikiki experience, combining...
2 BDRM w/ 4 Beds + 2 Bath + Parking + Partial Ocean View, 2 mins walk to Beach
Legal vacation rental at a fabulous location! This renovated 876 sq ft, 2 bedroom 2 bath with 2 balconies home is across from ‘Alohilani Resort, Steps away from the Waikiki Strip (Kalakaua Ave) and Waikiki beach! There are endless shopping, dining, and activities within...
Tropical apartment with amazing water views & rooftop pool - prime location
Marina Views Studio - Ilikai, 941Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha is abundant at this immaculate Honolulu studio! Centrally located, you can shop, dine, and sit...
Renovated 1-Bedroom At The Ilikai Hotel!
Look no further, you've found PARADISE! This condo has a King bed with a sofa sleeper in the living area. There is a sliding shoji door that separates the living area and the bedroom for added privacy. With a full kitchen, you can prepare your meals or enjoy the many...
Beautiful Oceanfront Condo on West Side of Oahu. Spectacular Sunsets
ALOHA, this beautiful, white sandy beach front home is located, right in front of Turtle Cove Beach. Not to mention, that it is also close to the world famous Makaha Surf Beach. Of course all the beaches on the West side are beautiful and is one of Oahu's best kept...
Luxurious, Spacious, High-end Beachfront Vacation Villa Free Parking
Dreaming of a memorable yet affordable Hawaiian vacation? Our Villa is calling you! It is located on the sunny Western shore of Oahu, and was built as a paradise for family-oriented beach lovers. It is landscaped with beautiful palm trees, koi ponds, a sandy-bottom...
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!
Indulge in an Unforgettable 30+ Night Stay at Our NEW Luxury Beach House at Kailua BeachImportant Compliance Notice: This home is available only for stays of 30 nights or longer, in full compliance with Kailua’s strict short-term rental regulations. We appreciate your...
Watermark - Luxury 2BD/2BA/1PA on 22nd floor with an Ocean View!
This unit has 1 queen size bed, 2 twin size beds, and 1 sofa bed, and can accommodate maximum of 5 people. This picture-perfect luxurious unit has 2 bedroom/2 bathroom/1 parking. From the bedroom, you are able to see the brilliant view of Ala Moana Beach from a window...
Center of Waikiki - 1 Bedroom 3 Queen Size Beds
THOUGHTFULLY CURATED BY OWNER/ARCHITECT TO CREATE A STRONG SENSE OF BELONGING.YOUR ULTIMATE HAWAIIAN RETREAT IN THE HEART OF WAIKIKI31st-floor corner unit in the Island Colony Aqua hotel building. You are in the CENTER of Waikiki, surrounded by shops and shopping...
Kahala Beachfront Estate – Private Resort-Style Living
For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10 Night Minimum over the Christmas/New Years Holiday Season at $7,500 per night.Spacious beachfront estate is situated on lush tropical grounds, nestled in...
Spacious Luxury Suite w/Mountain, Ocean, & City view at Royal Garden Waikiki
Escape to paradise at The Obsidian Oasis—a spacious 750 sq ft suite, newly renovated and upgraded for luxury and comfort. Located in the renowned Royal Garden Hotel in the vibrant heart of Waikiki. Perched on the 23rd floor of a 25-story boutique hotel, this unit offers...
Tropical Paradise Getaway Ocean & Lush Tropical Views Pool, BBQ & WI-FI Inn on the Park 1503
Tropical Paradise Getaway Ocean & Lush Tropical Views Pool, BBQ & WI-FI Inn on the Park 1503Enjoy relaxing lanai Ocean, Diamond Head & Tropical views Peaking above the Waikiki Skyline. Clean completely remodeled & newly furnished air conditioned studio suite with...
Aloha Suite Near the Sea IV, 3 Block Walk to Beach
TMK260230500082, TA-166-694-5024, STR# 2667 Convenience & 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!3 Additional studio suites available same...
Fairways Ko Olina 27H: Your Ultimate 3BR Retreat in Hawaii with Resort Access
Welcome to Fairways at Ko Olina 27H, a spacious three-bedroom, two-and-a-half-bath townhouse offered exclusively as a monthly vacation rental within the gated Fairways community on Oahu’s sunny west coast. This comfortable home blends open living spaces with serene...
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option
Aloha and Welcome to Kolea LandingA short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house is the perfect blend of island and modern living. Our guest house has a master bedroom (king bed) with an en suite...
Waikiki Banyan Condo With Panoramic 37th Floor Ocean Views by Koko Resort Vacation Rentals
Panoramic 37th Floor Ocean Views, Free parking & Wi-Fi The pool and all associated amenities will be closed starting April 7, 2025,for an estimated duration of 10 to 14 months to accommodate the RecreationDeck renovation project. Enjoy panoramic views of the ocean and...
Sweet & Cozy in Honolulu Free WIFI & AC
Summary:Welcome to the heart of Honolulu. Sweet and cozy one bedroom will newly updated kitchen and bathroom vanity. Keep it cool with A/Cs in the living room and bedroom. Relax poolside on your day-off.Complimentary Wi-Fi and parking stall provided.Perfect for all...
Surf's up on the North Shore and our condo is ithe perfect place to Hang Ten! You'll appreciate the attention to detail, modern amenities and the chic, decor when you escape to our Surfer's Paradise. Our location provides easy access to the surrounding amenities, and we...
Tidepool Getaway: 5 BR Oceanfront Estate - Sleeps up to 17
Tidepool Getaway is a unique and peaceful oceanfront escape located in Kahuku, Oahu. This expansive property features 3 living spaces featuring 5 bedrooms, 5 bathrooms, and 2 kitchens—ideal for families, multi-family gatherings, or groups of friends seeking both...
Our Place of Joy: An Ocean Retreat
Length of stay: MINIMUM 30 NIGHTS. Monthly rental. Property damage insurance required.Kai Lani is a quiet gated community located in Ko Olina, a 640 acre oceanfront resort on West Oahu, the dry leeward side of the island. Ko Olina means 'Place of Joy,’ where the aloha...
Coconut Villa Entire home in Koolina Walking distance to the shops and beaches
Enjoy your morning coffee or evening cocktails out on our lush tropical lanai with the tranquil backdrop of the Ko Olina golf course. Take in the stunning sunsets from this perfect vantage point.Our villa is located in an ideal location; everything is within walking...
Breathtaking Ocean View with Private Pool!
30 Days or more Rental!Discover this 2-bedroom gem in Honolulu. This tranquil house features 1 king bed and 1 queen bed, perfect for a peaceful getaway. Bidet in the bathroom, along with amenities like AC, WiFi, and a washing machine. You're sure to make fantastic...
Three Bedroom Villa at The Beach Villas at Ko' Olina
* Book with confidence! This vacation rental is a LEGAL Oahu vacation Rental Operating in a Resort Zoned District and is not affected by passage of Bill 89. This Luxury Condo is a spacious and beautiful 3 bedroom, 3 bath, professionally decorated Villa with a beautiful...
Luxury Ko Olina Beach Villa B109 by Gather w/ Stunning Ocean & Kapolei Views
Ko Olina Beach Villas B109 is a ground-level oceanfront retreat in Kapolei's Ko Olina Resort. With two bedrooms, two baths, and sleeping space for six, this villa blends comfort, luxury, and direct access to the lagoons, making it the perfect escape for families,...
Hale Kaimana by Gather: Lux Gold Coast Condo w/ Ocean Views & Beach Access
Wake up to breathtaking views of Diamond Head and the Pacific Ocean at Hale Kaimana by Gather, a stunning oceanfront retreat located in the prestigious Colony Surf building on Honolulu’s Gold Coast. This 2-bedroom, 2-bathroom condo offers 1,867 square feet of elegant...
World Famous Kailua Beach Charming Cottage
Studio Cottage near Kailua Beach and Beach Park! Large, 200 square foot lanai, fully furnished. Nice neighborhood setting. You won't believe how close this is to the beach! Also close to Kalapawai Market and other Beach Shops & Food. All utilities - A/C, Cable,...
The Pool House: 6 BR Kailua Home with Pool, Walking Distance to Kailua and Lanikai
The Pool House in Kailua offers 3,200 sq ft with 6 bedrooms, 4 baths and one amazing pool. Located in a peaceful and lush neighborhood with views of the Ko’olau Mountain range, it is an easy walk to Kailua Beach, Lanikai Beach and Buzz's Steakhouse. The home offers a...
Newly renovated guest house with lush landscaping & gazebo
Honolulu HideawayOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the heart of Honolulu, this charming guest house offers a tranquil retreat surrounded by lush landscaping...
Welcome to South Sea Bungalows:South Sea Arts has grown beyond the gallery and restaurant designing to provide Polynesian culture aficionados, collectors of Hawaiiana and people who appreciate culture in an oasis to call home during their stay on the island of Oahu....
Most Luxurious Ocean Front Condo in Kai Lani, Ko Olina, Hawaii
Awaiting you in this tropical paradise is a luxurious 2 bedroom, 2 bath condo that has everything you need to relax and enjoy your time in Hawaii. Nothing was spared in this fully equipped and fabulously appointed condo, whether it be to read a book in comfort and...
Remodeled High Floor Waikiki Studio
This charming studio nested on 35th floor of the Hawaiian Monarch building is your perfect place to enjoy your Waikiki vacation! With awesome views of mountains and canal, the condo comes with a queen bed, a full bath and a kitchen that includes an induction cooktop, a...
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
"In order to comply with Oahu's 90 day minimum short term rental laws, we may not advertise to rent for a period shorter than 90 days."Come enjoy island life while staying in our newly built, 600 sq. ft. upstairs suite. Beautifully furnished with a modern meets the...
Mokulua Sunrise Ocean Villa Lanikai
Experience the ultimate Hawaiian escape at Mokulua Sunrise, a stunning 4-bedroom, 3.5-bath oceanfront villa nestled in the world-famous Lanikai neighborhood of Kailua, Oahu. With sweeping, unobstructed views of the turquoise Pacific and the Mokulua Islands, this...
Your Waikīkī vacation begins in this deluxe one-bedroom one-bathroom ocean view suite, which was updated in 2015. You’ll love the kitchen, which has lovely wooden cabinetry, stainless steel appliances, and a view! You’ll also have indoor eat-in dining for four, which...
Watermark - Luxury 2BD/2BA/1PA on 14th floor with an Ocean View!
This unit has 2 king size beds which can accommodate maximum of 4 people. This picture-perfect luxurious unit has 2 bedroom/2 bathroom with 1 designated parking spot. The condo is located at a very convenient location at the heart of Waikiki; only 7 minute walking...
Breathtaking Studio Ocean Views! Pool! Beach!
Summary:🌺 Experience the Ultimate Hawaiian Retreat! 🌺Escape to paradise in this beautifully renovated high-floor unit offering breathtaking panoramic views of the Pacific Ocean, Diamond Head, and the vibrant Waikiki skyline. Whether you're here to relax 🌊 or explore 🌺,...