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.
Dolphin House by Gather: North Shore Escape w/ Direct Beach Access
Welcome to Dolphin House, a breezy beachfront retreat in Laie on Oahu’s celebrated North Shore. This three-bedroom, two-bathroom home blends the timeless charm of island life with modern comfort, offering 1,500 square feet of open, light-filled living just steps from...
Sky Ala Moana 2908: 2 BR, 2 BA Condominium in Honolulu, Sleeps 4
This stunning 2BR/2BA condo is located in the brand-new Sky Ala Moana building, offering breathtaking ocean views and luxurious amenities. The unit features a spacious living room, a fully equipped kitchen with modern appliances, and two elegant bedrooms with...
Aqua Aloha Surf Waikiki 1007 | City View Suite – Pool & BBQ
Aqua Aloha Surf Waikiki #1007, Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, (1) Queens Sofa Sleeper, Sleeps 4 360 St FtAqua Aloha Surf Waikiki offers a range of accommodations that are perfect for couples and...
Hale Nalani O-202 a hidden Gem, comfort and fun
A Wonderful 3-Bedroom Villa to Enjoy the Beauty of Ko OlinaWelcome to your ocean-view beach villa, where privacy and beauty come together in a breathtaking setting. The property features serene koi ponds with waterfalls, a lagoon pool with a sandy beach for children, an...
Fairway Villa #2417 – 2345 Ala Wai Blvd(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)HIGH FLOOR! TOP TO BOTTOM RENOVATION! Your Home Away from Home! Enjoy this recently renovated two-bedroom, two-bath condo (723 sqft plus 151-sqft lanai) with all...
Beautifully Remodeled studio Makaha Valley Towers
Beautifully remodeled studio apartment with breathtaking views of the mountains and ocean. The Makaha Valley Towers is located in the scenic Makaha Valley and is minutes away from Makaha Surfing Beach. The area is known for its quiet, relaxed atmosphere. There are...
Majestic Mahakea – Oceanfront Oasis on Oahu's North Shore
Majestic Mahakea Oceanfront Oasis invites you to experience beachfront luxury on Oahu’s fabled North Shore. This modern two-story residence sits directly on Mahakea Beach, where turquoise waves meet a lush mountain backdrop. Designed for both serenity and connection,...
Luxury Living in Allure Waikiki with Free Parking
Indulge in an elegant and spacious 1 bed 1 bath plus powder room with large balcony luxury condo unit in the prestigious Allure Waikiki. The unit is conveniently located at the edge of Waikiki. A premiere destination for world class shopping on Kalakaua Avenue's luxury...
Hale Pono- Oceanfront, private, gated, great views, AC, large property
Welcome to Hale Pono!The North Shore of Oahu’s premier luxury getaway.Please message me with any questions about available bookings.This hidden, elegant beauty sits on pristine property within the exclusive, gated community of the Sunset Beach Colony. Surround yourself...
Experience local-style living in the cool, quiet, and tranquil Pupukea. This brand new house is a perfect place to relax.Enjoy a private entrance and free parking. 5 minutes from Waimea Bay and other famous surf spots.Family-friendly, ideal for 4 people with the option...
*Affordable Island Getaway with private yard *
We're situated in a prime residential neighborhood, just 2 blocks away from Kailua Beach Park Entrance and Kalapawai Market, as well as downtown Kailua. You'll find an abundance of shops and restaurants, plus two of the world's most beautiful beaches, Kailua and Lanikai...
Watermark - Luxury 2BD/2BA/2PA on 36th floor with an Ocean View!
Discover a breathtaking retreat perched "on top of the world" with wide-open ocean views that showcase Magic Island and Ala Moana Beach Park. Experience the perfect blend of indoor and outdoor living with a stunning, usable lanai to savor paradise every day.LIVING...
Ocean, Marina, and Pool View 2BD Corner Unit w/ AC at the Ilikai Hotel
Experience the beauty of Waikiki with Happy Vacations, a short-term vacation rental company! Our team is excited to offer you a modern condo at the renowned Ilikai. Amazing views of the sunset with the sun gleaming over the ocean. During the day, you can embrace views...
Monthly- Discovery Bay 2203 Ocean/Sunset/Marina/City Views - Q Bed/Twin Sofabed
Sweeping Ocean Views High Floor Corner Unit, PremTV HBO, Remodeled. 5 Min to Beach, Ctrl AC, Furnished, Prking Incl, Spacious Lanai, Pool, HotTub, Utilities, WiFi, BBQ, Gym, Washer/Dryer, Beach Chairs/Boogie Board. Non smoking. Queen bed/Queen Sofabd.Sweeping Ocean...
Monthly Discovery Bay 1713 Ocean/City Views 1 Bd 1Ba
WAIKIKI / OCEAN VIEWS, 5 Minute Walk to Beach, Remodeled, Furnished and Fully Appointed. No smoking condo. Parking, Pool, Utilities, WIFI, BBQ, Gym, Sauna, Security, Washer/Dryer Included. Monthly.Excellent Views from Breezy Lanai, Tasteful and Clean. Monthly / contact...
High Floor, Drink Station, 2 Pools & Free Parking!
Summary:Welcome to our "Plumeria Suite" - A vibrant, stylish apartment, with fully stocked kitchen, located in the iconic Ilikai. Very short distance from the Pacific Ocean, Duke's Lagoon, Magic Island, Ala Moana Center and an abundance of shops and restaurants.The...
"Hale Pohaku" - Waimanalo Beach Front Vacation Rental
This property is a licensed short-term vacation rental Non-Conforming Use Permit #1990/NUC-1689. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, License # TA-059-395-6864-01. TMK 410040420000."Hale Pohaku" - Waimanalo is a...
Executive Gold Coast Oceanfront Suite: Diamond Head Views, Amazing Seaside Pool
Executive Gold Coast Oceanfront Suite offers refined island living with nearly 360-degree views of Waikiki’s Gold Coast, Diamond Head, and the blue Pacific. This two-bedroom, two-bathroom retreat at Coral Strand blends tropical elegance, modern convenience, and an...
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...
Waikiki Shore Beach Front Studio
Large beach front studio (460 sq, ft,) located at the Waikiki Shore, the only condo building in Waikiki that is directly on Waikiki Beach. This unit is located in a building that is within the designated Resort Zone, and therefore eligible for short term vacation...
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck
Tastefully remastered, 1937 cottage + rooftop lanai and BBQ area. The Kailua Beach Hideaway is tucked up on the hillside above the beach park, on a private lane. Ocean, park and Mountain view’s are captured from the rooftop sun deck. The Set Up:Cozy and efficient floor...
Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise
Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, deciding whether to go to...
Beachfront Paradise/Ocean Views & 5 Star Reviews/ Shared pool. Steps to the Sea!
paradisesandshawaiirentals.com8083828016E komo mai — welcome to our Turtle Bay Ocean Villa! Nestled within the iconic Turtle Bay Resort, this newly updated and beautifully redecorated 1,700 sq. ft. villa is designed to make your Hawaii vacation dreams come true. Located...
Aqua Aloha Surf Waikiki 211 | Sparkling City Views – Pool & BBQ
Aqua Aloha Surf Waikiki 211 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (2) Twin beds, Sleeps 2, 222 Sq FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for couples and solo...
You're Resort Home! Walk to Disney, Beach & Pool!
It can’t get any better than Hawaii resort living in Ko’olina! Make yourself at home in this beautiful, bright, fully equipped family home. There are plenty of comfortable work-friendly spaces & fast reliable WiFi. Soak up the sun at the pristine Ko’olina beach lagoons...
Masterfully Renovated Ocean View Unit in Waikiki
One of our best listings! Bright and Light One Bedroom, One Bathroom and One Parking (Max 6ft) at the Waikiki Banyan. Full of natural light during day! This partial Ocean View unit in the heart of Waikiki will make your stay in paradise a memorable one.Total of 3...
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family and close to amenities. Our luxury bedding and upgraded style...
Tranquil 2-Bedroom Getaway at The Cove Waikiki
Stay in seclusion & serenity at one of Waikiki's newest gems, The Cove Waikiki. This private community is nestled 2 short blocks from Duke Kahanamoku Bay and among Discovery Bay's ample shops, cafes and activities, and easy access to Waikiki, Magic Island Beach Park,...
Awesome Ocean View Studio 34th Floor Near Everything in Waikiki!
The view is awesome from this newly remodeled, spacious studio condo on the 34th Floor of the Hawaiian Monarch, just a few blocks from Waikiki Beach! This clean, modern, luxurious space is in a great location to enjoy your vacation in fabulous Waikiki Beach. In this...
This newly renovated luxurious Villa is nestled in the quiet neighborhood of Ko Olina Kai. This Villa has 3 bedrooms and can sleep up to six guests. Choose to spend your days on the Ko Olina Championship golf course or at one of the 4 lagoons located within the...
1-Bed, 1-Bath - Walk to Beach. Inquire for May and June.
Private, detached, gorgeous, newly built, fully equipped, one bedroom guest house ready and waiting to be booked by you! Superb location! Short walk to beautiful parks and beaches and minutes drive to historic Haleiwa Town.This incredible, newly constructed modern home...
Surfer's Paradise - Beachfront Vacation Rental on Oahu's North Shore
Nestled along the scenic coast of Haleiwa on Oahu’s famed North Shore, Surfer’s Paradise blends the relaxed rhythm of island life with panoramic ocean views and breezy, artful interiors. With 1,624 square feet of thoughtfully designed living space, this home easily...
Close to Kahala Beach/Air Conditioning/Heated Pool/Clean/Quiet Neighborhood
Ask owner about available dates/rates. Elegantly remodeled in 2018, this one level, very clean, 4 bedroom & 3 bath home, has 2 master suites, a gourmet kitchen, air conditioning in every bedroom & high end finishes throughout this private oasis. Please inquire about...
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,...
Makapu’u Hale, Literally oceanfront! VIEWS! A/C, 2 bedroom/2 bath
We are literally oceanfront! E Komo Mai (Welcome) to Paradise!30 Day minimum stay required by Oahu OrdinanceOur homes are fully furnished with everything you need for an ideal Hawaiian vacation!Makapu'u Hale is 2 bedrooms, 2 baths, newly decorated with comfortable &...
Marriott Ko Olina Beach Club Studio -Read Description!
“This is a timeshare. While the amenities and features will be the same, you may not get the exact unit shown in the photos.”Units are assigned at check-in. Some units categorized as "Ocean view" may have obstructed view to the ocean.Welcome to our Marriott Ko Olina...
Ocean View•1 BR Corner Condo•Mins to Waikiki Beach
Experience breathtaking, panoramic ocean views from this stunning top-floor 1-bedroom condo in the heart of Waikiki. This spacious retreat offers an open, airy layout with original hotel finishes, large windows, and a private outdoor dining space perfect for soaking in...
2 bedroom 1 bathroom, walk to world famous Waikiki beach only 0.3mi
Cozy 2 bedroom condo 805 sq.ft in Waikiki with great mountain and golf cruise view. North-facing floor plan, cool in summer time. Big balcony/lanai 125sq.ft one parking lot included in garage. Access to rooftop with great view. Shared gym and laundry in the building.
Welcome to Breath of Life, your serene escape in Makaha Valley! Perched on a prime lot with stunning ocean and mountain views, this peaceful retreat is tucked at the end of a quiet cul-de-sac with no through traffic. With all bedrooms on the first floor, it’s the...
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...
Waikiki Banyan Condo With Panoramic 37th Floor Ocean Views
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...
Welcome to our 2 bedroom Waikiki Shore Condo. This exclusive Waikiki Shore Condominium is located directly on Waikiki Beach, and is the only privately owned condominium building on Waikiki Beach, and sharing this world famous beach frontage along with some of the finest...
Luxury Laie Beachfront Estate w/ Private Pool, Spacious Living & Ocean Access
Welcome to Laie Beachfront Estate by GatherExperience the beauty of Oahu’s North Shore at Laie Beachfront Estate, a luxurious oceanfront retreat where contemporary island design meets timeless comfort. Nestled along a half-mile stretch of soft, swimmable white sand,...
Beautiful Beach Villa in Oceanfront Resort
Your ultimate paradise vacation awaits you at the Ko Olina Beach Villas Resort, Oahu's premier Oceanfront resort. Stay in this beautiful two bedroom/two bath luxury suite and enjoy sunset views from the expansive lanai. This spectacular beachfront resort features a huge...
Villa Olina Charming 3-Bedroom Villa On the Golf Course Steps Away from Lagoons
Beautiful & spacious yet cozy and comfy Ko Olina Kai Welcome to your tropical haven in the coveted Ko Olina Kai community. This delightful 3-bedroom, 3-bathroom house rental offers a prime location just a 10-minute walk from the stunning Ko Olina Lagoons. Tailored for...
Last Minute SUMMER DISCOUNT 2026-Pristine Haleiwa North Shore Beachside Retreat
4 Weeks for the price of 3!!! ----30 day minimum rental---- FIND PEACE & ESCAPE FROM STRESS HERE. -This is considered one of the best North Shore neighborhoods for location, privacy & safety. The large North Shore Winter surf is here! Check it out just minutes away down...
Kai Lani Luxurious Ocean View Gated Community, Two Master Bedrooms near Aulani
Please visit our exceptional vacation condo in the Kai Lani gated community, a part of the beautiful Ko’olina resort. Our ground floor luxury, executive-type condo is over 1300 Sq. ft. with a full ocean view from our lanai where you can sit at night viewing the sun set...
on THE SAND! Chuns Reef Beach House - Oceanfront Main House - A/C - Beach Toys
****Please note this property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied. Please inquire regarding availability for stays from 5 to 30 days.Chuns...
Kalo Homes ~ Tropical Makaha Sanctuary
Imagine waking up to breathtaking views of the ocean, mountains, and valley, while surrounded by lush tropical landscaping. You can unwind in the Jacuzzi or fire up the Traeger grill for a tasty BBQ. We`ve got you covered with all the beach amenities you`ll need to...
Surfer's Paradise: Waialua Condo Steps to Beach!
Experience the beauty of Hawaii at this cozy 1-bedroom, 1-bath vacation rental in Waialua. Relax with a book on the patio or walk to ʻĀweoweo Beach Park for world-class big wave surfing. This cozy condo also includes a flat-screen TV, a community coin laundry area, and...