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.
Ocean front 1-bedroom house, good location with AC, WiFi
Steps from the ocean. Escape to a cool 1-bedroom house by the Beach. This excellent property features a cozy queen bed, AC, WiFi, and a sofa bed. Guests can unwind in this serene space, just a stone's throw away from the beach. Kick back, relax, and enjoy everything Ewa...
Ko Olina Resort Vacation
Beautifully landscaped home surrounded by the famous Ko Olina golf club, a Ted Robinson designed 18 hole championship. Walk to Four Seasons resort, Disney Aulani Resort, Marriott Ko Olani Beach Resort , with all activities the lagoons and ocean will offer. Only 10...
Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops
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 Kahala Cottage by Gather, your...
Frontal 5-Stars Oceanview Beach Villas at Ko Olina 2-Bedroom & 2-Full Baths
2nd most reviews on VRBO!!! See other unit we have available: VRBO #311592The Resort: Beach Villas at Ko Olina.The Beach Villa is located at Ko Olina, Hawaiian for Place of Joy. Ko Olina is a picturesque resort located on Oahu's western side nestled away from the hustle...
Luxury beachfront villa on a world class beach in Kailua, HI
As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.This luxurious Kailua Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises...
Makaha Ocean View - 2 bedroom, 1 bath - family friendly
Hawaii License # 031-420-0064-01This property may not be rented for fewer 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.ABOUT THIS CONDO: Meticulously clean! This is a...
Steps to Beach-Heated Pool-AirCon-Gated Community-Min Stay 7 Nights-CONTACT HOST
THIS PROPERTY IS A LEGAL SHORT TERM RENTAL DAYS NOT SHADED (See Online/Inactive Calendar) ARE AVAILABLECONTACT HOST/RESERVATIONS & DETAILSThis beautiful four bedroom, four full bath air conditioned Hawaiian style home is just a short walk to pristine Kailua Beach....
Spectacular Diamond Head and Ocean View! Best location in Waikiki!
You'll love our 2 bedroom 1 bath unit on a high floor with the best views in Waikiki.Located a short 5 min walk to the beach and across from the world famous Hilton Hawaiian Village.Whether seated in the living room or relaxing in bed you'll be treated to a breathtaking...
Luxurious 3BR Fairways at Ko Olina 20G with Golf Views
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 Fairways at Ko Olina 20G by Gather,...
Pipeline Beach*apt* Clean* Wifi* White Sand Beach*30 night minimum*
The unit has a TV with cable, internet connection, a full kitchen with a stove top, refrigerator, microwave, toaster, blender, coffee maker, plates, pans, and other eating utensils. The unit is very clean, very comfortable with soft sheets. The interior is...
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...
North Shore Oasis, Hot Tub, across street from beach. Inquire for dates/prices.
Aloha and welcome to your retreat along the North Shore's 7 mile miracle. Right across the street from white sand beach and famous surf spots. Please contact us prior to booking at (808) 754-6453 or request booking or quote through VRBO. We can negociate the rate based...
Last Minute Spacial! Oceanview's on 31st Flr
**Notice:There is a one time check-in fee of $50.00 and $30.00/daily resort service fee for unlimited access to the building resort facilities. This fee is mandatory and must be paid during check-in at the hotel front desk.The daily parking rate is $39.00. Tax(17.962%)...
Gorgeous Ocean Views, Full Kitchen, Steps to Beach!
Waikiki Shore #1205 – 2161 Kalia Rd.Enjoy endless ocean and sunset views from your own private lanai! Come and stay in this high floor air-conditioned, ocean-view studio (347-sqft interior plus 61-sqft lanai) at Waikiki Shore, the only beach front condominium building...
Niki Lani Condo on the Golf course @ Turtle bay - Kuilima Estates West
*Newly renovated* 3 bed 2 bath beach condo that Sleeps 10+. Make this Island Oaisis yours! Discover O'ahu and enjoy the beautiful North Shore! Just a 5 minute walk to the relaxing beaches of Turtle bay and a 5-15 min drive to many legendary beaches with soft sand,...
Panoramic Ocean & Mountain Views -
Let the Aloha spirit be with you during your Hawaii visit by staying along the famous Koolau Mountain range on the lush Windward Side of Oahu. With 3900 sq. ft. of space to relax and enjoy a panoramic view of the grand mountains and the peaceful ocean as a backdrop,...
FOUR PADDLE Mountain view with full kitchen, AC, washer/dryer, Wi-Fi, parking
Four Paddle #2311 – 2140 Kuhio Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Located on the cool side of the building, you'll enjoy lovely Ala Wai Canal and Ko'olau Mountain views from this well-equipped 23rd floor one-bedroom condo (553 sqft...
Oceanfront Lanikai Beach Vacation Home
TA-006-302-3104-01Beautiful ocean front home at the beginning of Oahu's famous Lanikai Beach!. 2 bedroom, 1 bathroom main house and 2 bedroom, 2 bathroom guest cottage. Featuring breathtaking views, a brand new courtyard pool with privacy and manicured yard space, a...
Hot Deal! 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...
Waikiki Living, 4 blocks from surf, mountain views, king size bed and office!
Sunrise on the surf, sunset on the beach, dinner at the top of Waikiki. Enjoy views of Ala Wai canal, Ko'olau mountains and the new park on Aloha Drive from spacious lanais, including your own private lanai. Equipped with A/C, smart TV, microwave and a full kitchen to...
Massive 20% Discount for May & June at Aloha Nalu: Lux Home w/ Pool, AC & Views
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.Discover one of Oahu's luxury vacation rentals...
Waikiki Shore 1406
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,...
NAMI 1BR SUITE Luxurious Ocean View from 26FL
Nami, meaning "waves" in Japanese, symbolizing resilience and the ever-changing nature of life, is an integral part of the vibrant Hawaiian and Japanese culture surrounding Waikiki Beach. Our Nami Suite with breathtaking ocean view is 1 block away from Waikiki Beach....
Largest 3BR Villa in Turtle Bay Hawaii, nearest beach access!
Indulge in North Shore Luxury – Closest 3BR Villa to the Beach at Turtle BayWelcome to your ultimate Oahu escape — the only single-story 3-bedroom villa at Turtle Bay Resort, and the closest villa to the beach on the property. This expansive 1,700 sq. ft....
From 185 nt Aloha Summer Sizzle 2025 incl AC, 5 Star Luxury on the Big Island
Island breezes, fragrant blossoms, privacy - Na Hale O Keauhou, Hawaii's Best Kept Secret. This private 2 bedroom, 2-1/2 bath, 2 story town home is located in a 5 star, gated, luxurious resort complex with breathtaking, panoramic views of the ocean and mountains. Within...
Delightful Contemporary Honolulu Loft w/ AC & Laundry
*** Disclosure: All rooms are renovated in a similar fashion. Furniture style may vary in pictures and in the unit. Functionality are all the same. Queen size bed in bedroom, sofa bed in the living room. Your Honolulu adventure begins at this delightful 1-bedroom...
Ehukai Beach Hale: Newly Remodeled Ocean View Home With A/C, Steps From Pipeline
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.This updated Haleiwa vacation rental home is...
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
Please contact me for specific dates that you may be interested in.
This is your home away from home in an immaculate, spaciously designed guest house built for relaxing in comfort, style & convenience. This an attached 2 bedroom + 2 bath fully-equipped house + sofa bed and a very large stocked kitchen with a separate entrance and foyer...
New Remodel, Pool, Beach Access, A/C - Kuilima Estates West
Relax and unwind with your family in modern luxury. We’re excited to share with you our newly renovated oceanside condo. Nestled perfectly between the North Shore of Oahu’s world class surfing destinations and world famous golf courses - you’ll never be without...
Luxurious Two bedroom Unit with Panoramic Ocean View in ONE Ala Moana
This luxury corner unit has an epic panorama ocean view with floor-to-ceiling windows on 2 sides of the unit for a spacious feel. ONE Ala Moana is the pinnacle of world-class living. This unit has 2 bedrooms, 2 baths, and 2 parking stalls directly in front of the...
Modern Luxury Suite at Waikiki Beach Tower w/ Ocean View
Relax in this beautifully renovated unit with ocean views at Waikiki’s finest oceanfront condo building. Wake up to the crystal blue ocean from the luxurious king bed in the master bedroom, entertain family and friends in the open kitchen and living room, and enjoy a...
Amazing waikiki Beach condo 2Bed2Bath+free Parking
Listing descriptionAloha, thanks for checking in our property.A newly remodeled 2 bedrooms and 2 full baths (2023). There are 4 double and 2 single beds, full kitchen with kitchenette. It's spacious, almost 1,000 sq. ft. with a patio. It is on the top floor (17) of the...
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....
North Shore Beach House with AC, 30 day rental
LOCATION:**Message for special dates and availability not shown in the calendar**If you’re you looking for perfect white sand beaches with clear turquoise water & close proximity to everything in the North Shore, this is the place for you. Directly across the road is...
Unique Oceanfront Home in Enclosed Area
Kona Onenalo is a ONE-OF-A-KIND property on the beautiful Kona Coast. There are 12 identical and individual homes in this quiet, gated community. The complex sits on a point of land adjoining La Aloa Bay, and is just a 3 minute walk to Magic Sands Beach. You'll love the...
1 Bedroom AC Modern 5 Min Walk Beach
Turn key ready for a relaxing stay. With on site parking, a common use gated entrance leads you down a lava rock pathway to a private gated courtyard that contains a propane BBQ, water feature, patio table & chairs and lighted umbrella to enjoy your garden day or night....
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...
Luana Waikiki Premium Studio- Gym & Pool
Enjoy staying at our beautiful studio at Luana Waikiki! From the private lanai you can enjoy the ever-changing City views of Waikiki, Fort DeRussy Park, and through the palms trees even catch a glimpse of the ocean. Room features premium upgrades including upscale wood...
Beautiful "Beachfront" House on the Beach at Sunset Beach Paradise on the Beach
A Truly Luxury Beachfront House Located on World Famous Sunset Beach on Oahu's North Shore. Named 'Paradise on the Beach' at Sunset Beach by many guests this premier Direct Beachfront two-story, two large bedrooms, three full baths, executive style house affords the...
Wonderful executive home steps from a gorgeous beach
The Beach Haven is a beautiful home that can make your vacation very special. Only steps from one of the best beaches in Hawaii, you will feel the ocean breeze surround you. The home is treetop level which provides views of the ocean and of the Koolau mountains. This...
Pipeline Beach*Studio Large*AC*wifi*Free Pk*Steps To White Sand Beach*30nite min
The studio has a TV with cable, internet connection, air conditioner, a full kitchen with an oven and stove, a refrigerator, microwave, toaster, blender, coffee maker, plates, pans, and other eating utensils. The studio is very clean, very comfortable with soft sheets....
Ko Olina Kai Estate #20: Elegant Fairway Retreat with Luxe 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.Imagine yourself living the life of luxury in...
Le'ale'a by AvantStay | Ocean + Mountain Views!
Le'ale'a — that sunny, blissful feeling of wonder and joy you only feel when immersed in the beauty of a place like the Hawaiian islands. And there’s plenty of it here! In the heart of Mākaha Valley and surrounded by stunning tropical mountains, this bright...
Marine Surf Waikiki Studio
Location, location, location! Our elegantly appointed studio is a block from Waikiki Beach, and at the center of shopping, restaurants, and nightlife. We offer FREE parking, high speed WiFi, and a well-equipped kitchen with essentials for cooking. The lanai offers a...
Upscale Kailua Getaway: Steps to Swim Beach!
An unforgettable Hawaiian escape awaits at this luxurious 3-bedroom, 2-bathroom Kailua vacation rental home! Sip your coffee on the deck, then walk to Lanikai Beach to enjoy the morning waves. Spend your days relaxing in the private pool, lounging in the hammock, or...
Diamond Head Penthouse 2bed/2bath Kitchen & Parking in heart of Waikiki.
Minimum 30 day rental. Light and fresh beach Penthouse condo in the heart of Waikiki. Enjoy Diamond Head and ocean views from the large breezy lanai. Walk 3 min to shopping or 5 min to the boards and beach essentials provided! Relax in a stylish living room with WiFi,...
The Love Shack island getaway - minutes from Waikiki
The Love Shack Beach House - all the convenience of Waikiki without the hassle and noise. Walking distance to Waikiki, Diamond Head, beaches, the zoo, Kapiolani park, surf spots, snorkeling, swimming, great restaurants & bus stops. No need to rent a car if you don't...
Resort Style with Hula Show, Fireworks and even Tiki Torches!
The Ilikai is the first hotel-resort condominium developed in Hawaii and is one of the original landmarks of Waikiki. It is best known for being featured in the Hawaii 50 TV series and is loved by tourist and locals alike. Conveniently located in Waikiki next to the...
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...