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.
Available and legal for stays less than 30 days.
Hawaii Sheffield House has been a legal bed and breakfast for over 35 years. We are available and legal for stays of less than 30 days. We provide a unique neighborhood stay in Kailua Hawaii that is just down the street from Kailua Beach.The Hawaii Sheffield House...
Ko Olina Beach Villas 410: 4th Floor Ocean Front, Gourmet Kitchen, Private Lanai
Step into the world of luxury at Ko Olina Beach Villas B410 by Gather. Located on the fourth floor, this two-bedroom, two-bathroom oceanfront villa offers breathtaking panoramic views and elegant finishes. Perfect for up to four guests, it’s the ideal Hawaiian retreat...
Hale Kahakai | Ko Olina | Beach Villa w/ Pool!
Summary:Welcome to Hale Kahakai in Ko Olina! Nestled between exotic gardens and shimmering koi ponds, this charming paradise beckons vacationers looking for a secluded tropical escape. Maximum occupancy strictly enforced in accordance with local ordinances.The...
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...
Steps to Beaches, 2 King Suites, Private Pool, AC!
Spacious villa in Keauhou Resort just one block from He'eia Bay and two blocks from Keauhou Bay. Walk to Kona Country Club's ocean golf course, with resorts, shopping, and dining nearby. Perfect for relaxing with family and friends, featuring designer furnishings,...
Ko Olina Beach Villas O425: Oceanfront Getaway
Ko Olina Beach Villas O425 welcomes you to upscale island living on Oahu’s sunny west coast. Perched on the fourth floor of the Ocean Tower in Ko Olina Resort, this two-bedroom retreat blends sweeping Pacific views with breezy, open interiors and resort-style...
Hale Hina ~ Private, Peaceful, Perfection!
Welcome to Hale Hina - The Home of the Hawaiian Goddess of Sunrises, Sunsets, Coral Reefs, and the Moon! Our home is very special, and has many fabulous features and amenities, including the most important and maybe the most intangible one: Hale Hina is our vacation...
Hale Akaka Falls O-121 one of a kind luxury stay
Welcome to Paradise at Hale Akaka Falls O-121Discover the beauty and elegance of this stunning three-bedroom, three-bath villa located in the prestigious Beach Villas at Ko Olina Resort. This luxurious, ground-floor home offers a rare combination of comfort, style, and...
Holiday Sale! Turtle Bay Villas 311 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!Prepare to settle into island time a little easier with the unparalleled accommodations and amenities that await you at Turtle Bay...
Hale Mahina: Gorgeous Remodeled Pupukea Home with Private Hot Tub & Ocean Views
Enjoy the Flexibility of a Monthly Stay!This property is available for monthly rentals, offering you the comfort and convenience of an extended getaway. Whether you stay for a few weeks or the full month, you'll enjoy a consistent, all-inclusive monthly rate—no need...
PANORAMIC GOLF COURSE VIEW HOME "C", MODERN-CLEAN-GATED, NEAR PEARL HARBOR-JBPHH
Welcome to Hillside Perfection on the Greens at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, 4.5 bath air conditioned executive home located in central Honolulu. Perfect for leisure visitors, savvy business travelers and visiting construction teams...
AMAZING OCEAN VIEW Popular White Sands Village Steps To The Beach!!!
Hale Lihi LaniOcean View Vacation Rental at White Sands Village. We are located 4 miles south of charming Kailua-Kona Village and directly across from Kona's spectacular Magic Sands Beach. You will enjoy beautiful ocean views and dreamy sunsets from our large covered...
New! Kona Reef Resort Oceanfront 🌊 2 Bdrm, 2 Bath D-11 🏖 Right on the Ocean!
Wonderful Ocean Views Throughout your Spectacular 2 Bedroom, 2 Bath Condo! When you are dreaming about your much deserved Hawaii Oceanfront Getaway, this condo will exceed your expectations!Your ocean view lanai (balcony) is ready for you to dine, read, rest and enjoy...
Adorable Guest Cottage with Lanai -sleeps 3
This adorable 2 bedroom 1 bath Guest House is in a country like setting surrounded by sounds of nature and overflowing with ambiance. Located at about 1000 ft. above sea level, you will be serenaded by coque frogs , roosters, turkeys and chickens. There is a picnic...
Ilikai Hotels Best Kept Secret!! Updated & Furnished with Yacht views!
Conveniently located on the 3rd floor of the Ilikai Hotel, this condo is perfect for your time on Oahu. With the convenience of full kitchen, two bedrooms, two bathrooms and two spacious lanai this is a great choice when traveling with friends or bringing your family....
Perfect Family Beach House. Walk out gate to Amazing Beach.
The Waialua Beach House is located on the North Shore of Oahu, just steps from the beach. It’s only 2 miles from Haleiwa and its shops and restaurants and a short drive to the famous surf spots of Sunset, Pipeline, Haleiwa and Waimea. This recently remodeled and...
Kona Palms#201:Oceanfront with great views, AC, elevator and wraparound lanai
Gorgeous views from this spacious and updated 1041 square foot condo with 2 bedrooms, 2 bathrooms and Sleeps 5 to 6! Picture yourself relaxing in this absolutely beautiful condo, enjoying the ocean views, while watching surfers and the magically blue waters of the...
Top-Floor Luxury: Rare 3 Lagoon View, 2 Lanais near Disney Aulani, Avail Jun15th
Nov 13th next available. Note: We are the homeowners. Not managed by Vacasa or other troubled rental agencies.Our upscale beach home is ideally located on lagoon two, boasting some of the most spectacular ocean views at our resort from our two ocean facing lanais, a...
Lucky you! 2 Bedrooms, Large Lanai, Stunning Mountain Views, Pool, Parking, W / D
Whether you are coming to Waikiki on business or just to escape the stress of business with a vacation, you will find this 2 bedroom condo in a very desirable building your perfect tropical oasis. Designer -inspired décor echoes the peaceful colors seen in the...
Oceanfront Kona Home w/ Beach Access & Views!
Escape to paradise and immerse yourself in the beauty of Kailua-Kona, HI, at this stunning 2-bedroom, 2-bathroom vacation rental house. Just steps away from the picture-perfect beaches, this tropical retreat is your gateway to adventure. Discover the natural wonders of...
Red Ginger Garden Studio
Peaceful, well appointed room with private entrance ,down a flight of stairs, overlooking our back yard garden of fruit trees and red ginger blooms. Private bath with shower, queen bed, walk in closet, kitchenette, outdoor seating; Wake up and pick fruit for breakfast...
Stunning KoOlina Kai 2BR/2BA Condo sleeps 4
This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. This property has a mandatory 30 day minimum. This property may not be rented for less than 30 consecutive days. Rental prices will...
Right On the Water, Stunning Ocean views and Sunsets, AC, Elevator, Pool
Hale Kai a 2 bedroom condo at the oceans edge overlooking two amazing surf spots our condo is breathtaking for relaxing and listing to the ocean waves and watching the magnificent sunsets! Enjoy coffee in the morning while watching dolphins frolicking and seasonal...
Aloha Condos, Kanaloa at Kona, Condo 3703, Oceanfront, AC
1700 Square feet of breezy vaulted-ceiling living space, with new tile floor and paint throughout. Refinished koa wood cabinetry in all new kitchen. Ceiling fans in all major rooms and lanai (5). Powerful whole house ventilating system reduces demand for AC. High...
Kahalu’u Surf and Snorkel Beachfront Paradise, with Hot Tub
Incredible views of the bay and surfers! Modern house(built 2014) with A/C, across the street from Kahalu’u Beach. This is the BEST snorkeling and surfing in Kona. Surfboards,The Kona Trolley stop, and food trucks are steps away. The house has a hot tub, 4 bedrooms,...
13th Floor Waikiki Shore - Ocean-front / King Bed / AC
Welcome to Waikiki Shore – Your Perfect Oceanfront Escape!Located in the heart of Waikiki, this stunning 1-bedroom, 1-bathroom condo offers unbeatable ocean views and direct access to the world-famous Waikiki Beach. With modern amenities, a prime location, and a...
Marriott's Ko' Olina Beach Club (mountainview). Inquire first before booking.
Cross posted on Airbnb_platform as well. Cheaper there as it does not charge Hawaii state taxes. This is a Marriott Vacation Club property. Multiple rooms can be booked for same dates. If your dates aren’t available in same room layout and view for entire stay it may...
Hualalai Resort: Ground Level Villa by the Ocean
Hillside 1102 is nestled near the shore in the exclusive 5 Star Four Seasons Hualalai Resort. From the lanai, listen to the rhythmic waves on the shore, just a short walk from the Villa. Fully receding pocket glass, screen and shutter doors capture warm ocean breezes...
LUXURY GOLF COURSE FRONTAGE HOME "D", MODERN CLEAN, GATED, Nr. JBPHH, CAMP SMITH
Welcome to Hillside Perfection on the Greens at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, 4.5 bath, air conditioned executive home located in central Honolulu. Perfect for leisure visitors, savvy business travelers or visting construction teams...
Luxury Living at ONE Ala Moana
Welcome to the beautiful, One Ala Moana, one of the finest luxury apartments in Honolulu.With just 206 units, this unique building provides a rare sense of intimacy often missing in Honolulu. What does that mean for you? It means no long waits for the elevator, a lounge...
Wonderful Ocean View –Totally Renovated-On Golf Course
STVR-19-358846 - Relax and pamper yourself in luxury in this well-appointed condo. On the golf course with Spectacular Ocean views. This is NOT your average condo rental! This condo has had an extensive high-end renovation and interior decoration including art from...
Modern, Romantic Vibes in the Tropics
The SpaceCome enjoy this newly updated, spacious end-unit condo in beautiful Turtle Bay. It is as comfortable as it is beautiful. Whether it's breakfast in bed or a drink on the lanai swing, you may not want to leave. Everything has been updated, including hand-picked...
Hawaii Oceanview Oasis: Come to Work, Play, Relax.nOn Ironman Path!
Welcome to your dream Hawaiian escape! This spacious 3-bedroom, 3-bathroom ocean-view condo offers the perfect blend of comfort and convenience, making it an ideal retreat for couples, families, remote workers, or anyone seeking a rejuvenating getaway. Enjoy the unique...
Gorgeous Keauhou Resort Condo!
1B/1b Short distance to beautiful Keauhou Bay (5 min walk)Please read completely, so that there are no surprises upon your arrival! ❤■ We love the open air lifestyle and find it comfortable with the doors and windows open and the fans going. The breeze on the island...
SEArider TWO at Turtle Bay (1 bedroom / 1 bath) - Kuilima Estates East
Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal...
Gorgeous Ocean View! Steps to Beach! Centrally located, full kitchen & more!
Waikiki Shore #712 – 2161 Kalia Rd.Waikiki Shore is the only condo in Waikiki where you can step directly from the building onto the sand of Waikiki Beach!You'll be mesmerized by the incredible ocean views from this beautiful Hawaiian feel contemporary. The open...
Mauka Sunrise, Walk to Hau‘ula Beach & Trails, A/C
Welcome to our tranquil three-bedroom vacation retreat nestled in the heart of nature's paradise. Each bedroom boasts a comfortable queen bed, ensuring a restful night's sleep for everyone. The master bedroom features a convenient in-suite full bathroom with a...
Chic Beachy Studio in Waikiki
Beachy style, chic studio renovated to 5-star standard with partial ocean view. Centrally located at Marine Surf Waikiki on 21st floor. Just steps from the beach, world-class shopping, restaurants, and attractions. One block from Royal Hawaiian. Enjoy a sleek place to...
Ocean Front! Stunning Remodel in 2024! 102 Kona Riviera
Ocean Front Stunning Remodel in 2024Kona Riviera #102Bedroom Configuration:Master Bedroom: King Bed Living Room: Sleeper SofaAmenities:Beach Equipment: All of our vacation rentals include beach towels for the maximum occupancy, four beach chairs, two boogie boards, one...
New Upscale Kona Retreat, Ocean Views, Pool, BBQ
Welcome to paradise in Kailua-Kona, Hawaii! 🌴 Escape to this stunning 3-bedroom, 2-bathroom oasis boasting breathtaking ocean views and a private pool for the ultimate Hawaiian getaway. Wake up to the panoramic views of the Pacific Ocean right from your private...
Kailua-Kona Condo w/ Pool & Ocean Views
A tropical Hawaiian getaway awaits your arrival at this updated Kona Coast condo perched above Keauhou Bay! Upon entering the unit, guests of this 2-bed, 2-bath property are treated to a quintessential island experience with a contemporary flair. Whether guests spend...
Charming 1-bedroom condo in awesome Kuilima, Kahuku, Oahu
Beautiful, gated Hawaiian-style condo. Steps to tennis courts and pools! Walk to the beach to surf, snorkel, sun bathe or people watch.Need more space for a wedding party ? Family Reunion?Neighbor units also available! This Kahuku condo boasts 1 inviting bedroom with a...
Sea Village Oceanview Condo
Unwind with modern comforts, including a flat-screen TV with cable, high-speed WiFi, and a fully equipped kitchen perfect for preparing island-inspired meals. Step outside to soak up the sun in the oceanfront complex, where you can lounge by the pool, take a dip in the...
Cool retreat at the entrance to Lanikai. Very Close to Beach. 3 Primary Bedrooms
Live your best life! An opportunity for beach living in this renovated and updated luxury rental with views of Kailua Beach and Kailua Beach Park - it's brilliant turquoise blue ocean, sandy beach, large grassy areas and tall ironwood trees. Fine craftsmanship abounds...
Renovated Waikiki Studio, Full Kitchen, Free Parking, 4 Blocks to Beach!
Fairway Villa #1109 – 2345 Ala Wai Blvd.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)NEW TO OUR INVENTORY! You'll enjoy this newly remodeled (August 2023) 11th-floor studio in the quieter east end of Waikiki. With a full kitchen, free Wi-Fi,...
Puuwai Alii Estate: Stunning Luxury Home with Pool, Hot Tub & Ocean Views,AC!
Absolutely amazing property! A one of a kind 5-bedroom, 6-bathroom property that is built to impress with gorgeous high end materials and is one of just seven properties in the quaint "Pu'uwai Ali'i" subdivision. The gated entrance, majestic surrounding trellises, and...
Makaha-465 Farrington: Spacious 4BR Oceanfront Haven with Modern Amenities
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.Escape to the enchanting shores of Oahu at...
Waimanalo Beach Cottages – Tranquil Island Retreat Steps from the Shore
Uncover the allure of Waimanalo and lose yourself in the tropical paradise of Waimanalo Beach, where our exquisite cottages and breathtaking surroundings await. Embark on a journey of discovery by indulging in the myriad of exciting activities we have to offer....
High Fl Mount&CityView 1BRw/2Free Park Wsher/Dryer
Centrally located in Waikiki, this High Floor 1-Bedroom, 1-Bath unit features your your own Juliette balcony/Lanai, in-unit Washer and Dryer, and rare 2 Tandem Parking Stalls included —Free! Max height for parking is 6'2". Sleeps 4 (2adult and 2 small children) with a...
Luxe Coastal View 2907C Villa at Hualalai w/ Resort Pool & AC
September 15 – Mid-November, 2025The Hualalai Resort Spa will be undergoing enhancements to the outdoor aqua-thermal areas of both the men’s and women’s locker rooms. During this time, massage, body, and facial treatments will be temporarily relocated to the...