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.
New low rates thru Mid-Dec 2022.... Weekly Housekeeping now included FREE!
TA-105-568-8704-01Enjoy your morning coffee in comfort on the master lanai and end the day watching the sunset from your own backyard. Spend days relaxing poolside while listening to your favorite tunes play throughout. Kalani Villa is the epitome of what a holiday home...
Fabulous Ocean & Diamond Head View 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...
4 Bedroom/ 3 Bathroom Private Home
This home includes ocean views, a rooftop deck, and a heated pool. Enjoy breathtaking views of the majestic lava-formed Ko'olau mountain range and only steps to the # 1 rated beach In the world (2015), Waimanalo Beach, famous for the filming of Magnum PI, Baywatch,...
Beachfront top-floor unit on Oahu's north shore!
LOWEST PRICE YET – 25% OFF FOR JULY 13–AUG 10, 2025! ONLY $130/NIGHT.This remodeled condo is on the top floor of a beachfront complex on Oahu's north shore. Experience the North Shore lifestyle, including breathtaking sunsets, world-class surfing, snorkeling, and...
Executive Balinese Vacation Home in Hawaii Kai
Find serenity,luxurious style, at Hale Maluhia. This Oahu vacation rental, whose Hawaiian name translates to "house of tranquility," is a beautifully contemporary resort close to some of the island's best beaches and east oahu coastline. Invite up to eight friends or...
The Crown Jewel of Kawela Bay! 30 day stay
Hale Keo Keo – Historic Beachfront Home on Kawela Bay, Oahu’s North ShoreWelcome to Hale Keo Keo, the only home built directly on the sand in Kawela Bay — a calm, crescent-shaped cove on Oahu’s iconic North Shore. With room for up to 17 guests, this rare...
Heart of Downtown 1 bedroom 1 bath condo 1 reserved parking
This 1 bedroom suite located in the heart of downtown in Executive Centre. Free parking is included! It is 15 minutes to Waikiki, airport. It has central AC, free wifi, and an on-site laundry room. If you don’t have a car, no problem, there are bus stops right outside...
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen
Nestled in the beachside community of Lanikai, Kailua, this fully furnished home is over 1400 square feet of island style living. Beautifully yet simply decorated, this unit is the whole upper half of the main house. The entrance is at mid-floor level with a Brazilian...
Waikiki Condo Has 2 Bedrooms & 2 Baths, with 1 free parking space.
This Waikiki condo was newly remodeled in June 2023, with 2 bedrooms, 2 full baths. The full kitchen has an oven, stove range, microwave, dishwasher and refrigerator, and includes fully stocked, large living room has a queen size sleep sofa/futon and 2 single full-out...
Charming Waialua Vacation Rental - Near Beach!
Experience the beauty of Hawaii at this cozy 1-bedroom, 1-bathroom vacation rental in Waialua. Relax with a book on the patio or walk to ʻĀweoweo Beach Park and catch the surf. This cozy condo also includes a flat-screen TV, a community coin laundry area, and a...
Waikiki Sunset 2BR - DIRECT Diamond Head View!
The best Diamond Head view in all of Waikiki is yours to behold from this immaculate, beautifully furnished and well-appointed condominium. This is for you, the guest who appreciates quality and value.A spectacular, direct Diamond Head view, Hawaii's most famous...
Coastal Chic Condo with Ocean View & Full Kitchen
Step into a bright and airy beautiful condo, where modern elegance meets coastal charm. Expansive windows invite natural light to flood the open living space, offering breathtaking views of the marina and the sparkling Pacific Ocean. From your private balcony, enjoy the...
Chic & Upscale Waikiki Beach Ocean View w/ 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...
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...
Ocean Frontage with Mountain Viewsn
Comfortable 1 bedroom apartment in the Iconic Ilikai Hotel and Luxury Suites. This is an owner unit with access to most of the hotel amenities. Parking in the building is by paid valet only, but there is also self parking available in the marina.The building has 2...
Luxury Ko Olina Beach Rental Panoramic Ocean View 3BR 3BA 8th floor 2 parking
Imagine yourself in a world-class Oahu, Hawaii oceanfront resort in Ko Olina beach rental bliss with exotic woods, natural stone, and an expansive lanai. Imagine as you lie down on a bed of total luxury. You sink down into silky softness that cuddles you as you are...
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...
Private One Bedroom Condo in the heart of Waikiki
Perched near the top of Foster Tower, this high-floor one-bedroom retreat offers an unrivaled vantage point over Waikiki. From the moment you step inside, the sweeping ocean and Diamond Head views create a breathtaking backdrop for your island stay. Sunlight streams...
Foster Tower Waikiki Beach Condo
Foster Tower is located steps away from beautiful Waikiki Beach. This is a one-bedroom unit in a highly desirable building and location. Enjoy beautiful ocean views and immediate access to the beach for surfing, swimming, and snorkeling, hundreds of restaurants, the...
Aloha Waikiki Condo 2Beds, 2Baths, Free Parking.
Aloha, thanks for checking in our listing. A Newly remodeled penthouse 2 bedrooms and 2 full baths. There are 4 queen beds and 1 single beds, full kitchen with kitchenette. It's spacious 1,000 sq. ft. with 2 patio and 3 Air-Con. It’s on 17 top floor with beautiful...
LUXURY 2-Bed Condo, Kitchen, Wi-Fi, Parking, W/D, AC, LEGAL Monthly Rental!
Allure Waikiki #804 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches throughout features...
Hawaii's Number 1 Luxury Condo "Park Lane" (30 Nights Minimum Stay)
Unit 8301 at Park Lane, offers 2 bed, 2.5 bath, spacious and open lanai with a barbecue grill and relax in your own private in-ground spa, over-looking Ala Moana beach park with a special ocean view. The interior is designed by Clifford Planning & Architecture LLC. The...
Hale Maluhia - Gorgeous Kaneohe Bay Home
Hale Maluhia (translates to peaceful and serene) is a bright and breezy home nestled in a quiet neighborhood by the bay with easy access to the H-3, Pali and Likelike Hwy. The lush Koolau mountains provide a picturesque backdrop like no other. Tastefully decorated with...
Comfy studio, King bed, kitchen & parking included with stay
This apartment is centrally located with a 5 minute walk to Waikiki beach.It comes with one dedicated parking space. The apartment has a king bed and one pull out full size sofa bed. There is a small kitchen with all things you need to cook small meals. Beach chairs,...
Kailua Beach Historic Renovated Cottage
This property is offered as a monthly rental. Although full-month occupancy isnot required, the monthly rate remains fixed and applies in full, regardlessof the number of nights stayed, as prorated rates are not available.One of the original homes on Kailua Beach, this...
Amazing Oceanview at Beach Villas at Ko Olina
Looking to enjoying your vacation up close and personal with Hawaii's beautiful beaches and ocean? This oceanfront villa is the one for you! You'll be impressed with the spectacular unobstructed ocean view. It's one of the rare villas that is situated in the resort so...
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...
Private Tropical Paradise in the Heart of the North Shore - beachfront community
[Oahu requires a minimum 30 day rental stay. All quotes will be returned for 30 days to ensure a valid stay duration]Aloha, we want to extend our home to your family to build great Hawaiian holiday memories on the beautiful island of Oahu.Located in the heart of North...
North Shore Getaway w/ Ocean Views steps to Beaches and Surf
This beautiful getaway features a secure gated driveway accessed by remote in which you will enter. Drive up left side of Garage to recessed home where you will access a set of stairs only accessed by you and your guests. This entry leads to an open floor plan Private...
Waikiki Park Heights 1208 Sun & Beach Fun only 3 minutes away
Waikiki Park Heights 1208 - Ocean-View Serenity Awaits – 30-day MinDiscover the true essence of aloha in Waikiki Park Heights 1208, a charming 1-bedroom condominium located in the heart of Waikiki, providing convenient access to the beaches, shopping, dining, and...
Escape to Paradise- AC, Kayaks,Ocean across street
*30 day rental. Please inquire.Come, Escape to Paradise! This beautiful secluded home is in the perfect spot along the Windward shore of Oahu. This 2500 sqft Ka'a'awa, air-conditioned home can sleep 8-10 people in 3 bedrooms and an open den. Planning on working from...
Luxury Ko Olina Beach Villa with direct beach view. Sleeps 6.
Premium Beach Villa very close to the beach. B-208 is the closest villa to the beach on the sunset side. Enjoy direct views of the beach and ocean without looking past another lanai. Enjoy added privacy and ocean views on the desired sunset side of the beach tower....
Kekela Nui Beachfront - Steps to beach + AC!!
*30-night rental*Are you looking for an affordable beachfront property that will fit the whole family and not break the bank? It is a private beachfront property that your family will enjoy and love. The ocean is just steps away. There are no crowds to fight, no public...
Hilton Hawaiian Village Lagoon
Beautiful two-bedroom two bath, city view 1,025 sq. ft. suite that features one king bed in the master bedroom, bathroom with standard shower/tub combination and TOTO washlet, the guest bedroom is furnished with two twin beds or two double beds, and a bathroom with...
Park Lane Ala Moana 8803
Welcome to the exquisite Park Lane at Ala Moana residential resort community. Park Lane’s luxury residences offer resort-like amenities and are ideally located in the heart of Honolulu, just across the street from Ala Moana Beach Park. Built on the ocean side of the...
Luxurious 2.5 Bedroom Unit with Panoramic Ocean View in ONE Ala Moana
This luxury unit has an epic panorama ocean view with floor-to-ceiling windows. ONE Ala Moana is the pinnacle of world-class living. This unit has 2 bedrooms plus a den, 2.5 baths, and 1 parking. One Ala Moana has a long list of luxury amenities and a great service team...
Hale Laule'a - North Shore Oahu Estate. Walk to Sunset Beach!
**In compliance with Hawaii vacation rental laws, this property is held for your exclusive use for a period of 30 days or greater regardless of your actual length of stay. Please inquire for details or questions regarding pricing and availability. Total pricing for the...
Peaceful North Shore Beach Oasis
Our beautiful 2 bedroom 3 bathroom house has direct access to one of the most beautiful beaches on the North Shore. The house is the last house on the beach so you have unobstructed views of a beautiful cove with warm, calm waters and a large horse ranch on one side....
Gorgeous 3 Bedroom Condo as Close to the Beach as You Can Get!! 30 day rental
Perched on the top floor of Foster Tower, this stunning three-bedroom penthouse offers an elevated island living experience with sweeping panoramic views of the Pacific Ocean, Diamond Head, and the Honolulu skyline. Designed for those who appreciate sophisticated...
Orchid House - Pool and Endless Ocean views!
ORCHID HOUSETA # 087-311-0016-01With magical views of the Mokuluas from most rooms, this 3 bedroom, 4 bath custom home was just renovated using exotic hardwoods and stone from around the world. Features include solid hardwood floors, granite countertops, slate stone...
Recently Renovated Studio in Palms at Waikiki
Sweeping views of Waikiki are visible from the 8th floor through the main living space through the floor-to-ceiling sliding glass doors. You will have access to the gorgeous outdoor pool, and fitness center, all just steps away from Waikiki Beach. IHOP restaurant in the...
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...
Secluded Beachfront Luxury, Highly Desired Location
10/3/24 DISCLOSURE: Home is listed for sale and guests will need to accommodate showings with 48 hours notice. Reservations may not be guaranteed if home sells or is in escrow prior to arrival.Two-story beachfront home in Mokuleia. Four bedrooms with King, Queen and...
Beachfront Estate On The North Shore with AIR CONDITIONING 90/TVU-0043
Hukilau Beach and the blue waters of the Pacific Ocean on one side and the Ko'olau mountains on the other, Hale Lani lives up to its name as the “House of Heaven.” The perfect choice if you’re traveling with a large family or a group of friends, this home is one...
North Shore Turtle Bay Hideoutn - Kuilima Estates East
BRAND NEW RENOVATION. This unit backs up to the world famous Fazio golf courses with a beautiful view of the 18th hole from the relaxing lanai. Just a five-minute walk from the beaches at Turtle Bay Resort and access to miles of walking and biking trails. Turtle Bay is...
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...
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...
Kuilima Condo on the 18th Hole - 5 Minutes to Beach
Aloha! Come enjoy your Tropical Hawaiian Vacation in our beautiful, clean, and relaxing one bedroom and two bath condo with all the conveniences of home. Our spacious condo is the perfect blend of tropical seclusion amidst all the amenities offered by a world-class...
Coconut Plantation 1086-1: Upscale 3BR Condo in the Serene Ko Olina Resort
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 Coconut Plantation 1086-1 by...
Island Adventure: Minivan Rental, Contact Us
Mahalo is the Hawaiian word for thanks, and a feeling of profound gratitude is what inspired this beautiful home. From the moment you arrive at Hale Mahalo, you’ll understand why. This lovely 3-bedroom, 3-bathroom home is a tribute to the stunning beauty of its...