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.
Cozy historic home in Manoa Valley, view of Diamond Head, walk to UH
Private home in a quiet historic neighborhood in Manoa Valley. This hidden gem is tucked away on a quiet little road, surrounded by greenery. Above the city with picturesque view of Diamond Head and mountainside rainbows in the day and view of Waikiki City lights and...
1BR Mountain View w/ Balcony, Pool & 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...
Club Wyndham Royal Sea Cliff, Kailua-Kona, Hawaii, 1 Bedroom Deluxe Suite
*** Sanitation/Cleaning Update ***Wyndham resorts have always met the highest standards of cleanliness, and now we are exceeding those standards with enhanced cleaning protocols and disinfecting measures, including the use of hospital-grade, virus-killing products...
Luxury 3BR Villa with Ocean Views – Ko Olina Beach Club Islan
Step into paradise in this ocean-view three-bedroom villa at Marriott’s Ko Olina Beach Club, where comfort, space, and resort-style amenities come together for an unforgettable Hawaiian escape. Ideal for families or groups seeking relaxation and adventure, this villa...
Ocean View Queen Room at Kaimana Beach Hotel | Right on the Beach
Nestled between the iconic Diamond Head and Waikiki Beach, Kaimana Beach Hotel combines coastal charm with easy access to local attractions. The Ocean View Queen offers partial ocean views and a relaxed island atmosphere. It's a perfect hideaway to watch the waves and...
The Grand Islander, a Hilton Grand Vacations Club - 1 Bedroom Premier Luxury - Ocean View
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Unwind in Style: Newly Remodeled Pacific Monarch with Spectacular Ocean Views!
Welcome to your new home away from home!Step into paradise with our beautifully remodeled Honeymoon Luxury Suite on the 25th-floor studio, offering mesmerizing east-facing views of the ocean that defy description. Nestled in the heart of historic Waikiki within the...
Oceanfront Paradise in the Heart of Kailua Kona with AC & Stunning Views
Welcome to Kona Alii, one of the most sought-after oceanfront condo communities in Kailua Kona! This beautifully updated 1-bedroom, 2-bathroom end unit offers breathtaking, unobstructed views of the Pacific Ocean from an oversized private lanai — the perfect perch to...
Beautiful Ali'i Lani condo-Full use
Welcome to your idyllic escape in the heart of Kona, located on the stunning Big Island of Hawaii. Nestled within the vibrant Alii Drive, our inviting condo is perfectly situated for an unforgettable tropical getaway. Immerse yourself in the beauty of Kona, where...
Enjoy this newly renovated beautiful and spacious studio located near Waikiki.
Enjoy this newly renovated beautiful and spacious studio. Located across the convention center and next to Ala Moana shopping center and beach. Walking distance to sandy beaches, Waikiki, shopping and more. Comfortably sleeps three with a Queen bed and Xl twin pull out....
North Shore Rustic Country Lodge 2-Story Yurt By Beach Waialua Haleiwa Glamping
Escape to this Tropical North Shore Island Nature Rental Retreat! 2.5 blocks to the beach & famous surf breaks. Rental is a 2-Story Yurt with a generous 1500+ square foot open-concept floor plan. Sleeps up to 11 people. Features kitchen & full bathroom amenities. Close...
Breathtaking Ocean View 2-Bedroom at Lanikea
Located at the beginning of Waikiki, this spacious apartment at the Lanikea building features unbeatable ocean views from the private lanai, 2 private bedrooms, 2 full bathrooms, open concept living & dining area, multiple workstations, hardwood floors, in-unit...
Escape to Paradise! Townhome in Coconut Plantation, just minutes from lagoons!
Welcome to the wonderful resort area of Ko Olina! Located within the gated community of Coconut Plantation, this gorgeous townhome offers guests the perfect blend of comfort and convenience, the ideal island getaway. Features of the townhome include: Prime Location:...
Hoʻonānea I Loko Kailua
If you're looking to work remotely, travel for work, remodel your home & have a place to live while it's worked on then this is the perfect home. This is a redesigned and remodel home that was originally built in the 1960's. The home is tastefully designed with a...
Velzey Villa by Gather – 3BR w/ Lanai, Full Kitchen & Washer/Dryer
Located just steps from Velzyland Beach on Oahu’s North Shore, Velzey Villa offers the comfort of a private 3-bedroom, 2-bath home with 1,232 sq ft of indoor living space. Designed for families, surf travelers, and those who want to experience Haleiwa at their own...
Ko'Olina, 2 Bed Ocean View Villa
If you want to truly relax, follow the thousands who have stayed at the 640 acre gated premium vacation ownership resort, Marriott Ko Olina Beach Club. Nestled on the West side of Oahu, this resort is surrounded by clear blue waters and a picturesque lagoon. Soak up the...
3-bedroom condo in welcoming Ko’Olina Resort with WiFi, AC. Relax and enjoy
Escape to this cool condo in picturesque Ko’Olina. With 3 bedrooms including 1 king, 1 queen, 1 twin, and 1 full bed, this fantastic property is perfect for families or groups. Enjoy the convenience of AC, WiFi, a washing machine, and more. The 2 bathrooms offer a...
Tradewinds Plaza Waikiki Oceanview Private Rental Sleeps 4
Escape to The Tradewinds Plaza in Waikiki TP606 - Your Ideal Vacation RetreatProperty Details:Address: 2572 Lemon Road #606, Honolulu, HI 96815Property Type: 30-day Minimum 1-Bedroom Vacation RentalEscape to The Tradewinds Plaza in Waikiki Suite 606 offers a spacious...
Ocean Front Pipeline Estate! Front row seat to the Pipeline Masters surf event!
Pipeline living at its best. A definite bucket list dream vacation destination. Facing directly at the famous Banzai Pipeline and Pipeline Backdoor, this home offers a unique spot to watch the most spectacular surfing waves in the world. This home offers all the...
Experience Island Paradise at The Grand Islander by Hilton - 2 Bd. Ocean View
Discover the perfect blend of fun, relaxation, and tropical beauty at The Grand Islander by Hilton Grand Vacations in Waikiki, an unforgettable family-friendly destination in the heart of Honolulu. Set against the lush, verdant backdrop of Oahu, this two-bedroom suite...
Couples Retreat! Pacific Vista w/WiFi and A/C– Waikīkī Shore 504
Welcome to your beach retreat in Waikīkī! Relax in this Studio Ocean View condo, which offers fantastic lanai views of the Pacific Ocean, Waikīkī Beach, and the palm treetops of Fort DeRussy Park. The private lanai has seating for two people and has a small table so...
Ko Olina Beach Villas O-906 | Oceanfront Lanai, Pools & Luxury 2BR/2BA
Ko Olina Beach Villas O-906 welcomes you to ninth-floor island living in Kapolei’s coveted Ko Olina Resort. This two-bedroom, two-bath vacation condo pairs sweeping ocean vistas with the comforts of home, setting the scene for families, couples, or digital nomads...
Live Local Redwood Pole house panaramic Ocean views quiet convienent nbrhood
. Wailupe is on mountain side , 5 blocks facing ocean. enjoy tennis, bball/park across street, great views. Convenient location to town, Waikiki 4 miles away. Two bedrooms in large great room. Main bedroom has a queen size bed, sons room has a twin, and living room has...
Ilikai Hotel Oceanfront, Top Grade Upgrades Throughout! 30-day Rental Only!
If you're seeking a place with stunning views, this condo is perfect for you! Don't miss out on this once-in-a-lifetime experience—book now!Experience the ultimate Waikiki luxury in this one-of-a-kind 3-bedroom, 3-bathroom condo at the iconic oceanfront Ilikai...
Highly desirable Deluxe One-bedroom City View Unit. Reserve Today, Will not last Long!!
1 Bedroom Deluxe City View on the 13th Floor! Look no further, you've found PARADISE! This condo offers the comforts and conveniences of home. It is well maintained, reasonably priced and conveniently located in Waikiki. This condo can comfortably accommodate 4, with a...
STVR Home-Hawaiian Living Oasis 4Bed/4Bath/Sleep 12/AC/Pool Coming soon
**New pool coming in Nov 2025**Welcome to your dream getaway in Kona! Nestled in a prime spot, you're just 10 minutes away from Kona's best beaches, restaurants, and attractions. Whether you're here to explore or relax, everything you need is within reach. This stunning...
The Cedar House - Private Yard and Entrance!
Welcome to The Cedar House! Just 5 minutes from world-class beaches and surf breaks. Enjoy country living with cool mountain breezes and the soothing sounds of nature, amidst coconut trees, bananas, and tropical plants. Local laws require a minimum 30-night booking, but...
Spacious 1BR Premier Suite at Grand Waikikian – Aloha Comfort in Waikiki
Experience a blend of tropical luxury and home-like comfort in this 1 Bedroom Premier suite at Grand Waikikian. With about 836 square feet, this suite accommodates up to 4 guests, offering plenty of space for families or couples wanting both relaxation and adventure in...
~NEW~ Oceanfront Luxury at Waikiki Beach Tower
Waikiki Beach Tower Unit 901 - 9th floorRelax in this beautifully renovated 2-bedroom 2-bath unit with ocean views of Waikiki Beach. Entertain with family and friends where the views from the kitchen and living room have you feeling like you're on the beach. Start your...
Vacation at The Coconut Plantation in the renowned Ko Olina Resort | TCP-1222-3
One Rate, You Choose the Length of Stay!All rates quoted will be based on a 30 day period. Our monthly rentals will be made available to you for your use and occupancy for a period of thirty (30) days. You are not required to stay for a full 30 day period. Just stay for...
3 BedroomSuite, The Grand Islander Resort
Enjoy the glamour of this stylish, upscale place. Situated in one of the most desirable locations in Waikiki, The Grand Islander is an elegant 38-story tower soaring high above the area's legendary coastline. The Grand Islander offers access to 22-acre Hilton Hawaiian...
Privately-owned 1 bdrm/2 bath suite in Imperial Resort Waikiki. Enjoy amenities & beach.
Experience resort living in privately-owned suite at Imperial Resort, in Waikiki core on Beach Walk. We are steps to beach, shopping and dining.This 1 bdrm, 2 bath suite is well equipped for comfort, with the essentials of home and luxuries of a resort.Enjoy roof top...
Cozy Ocean Stay 2BR unit
Escape the bustle of Waikiki and access some of the North Shore’s best beaches! You’ll be in proximity to Ahupuaʻa ʻO Kahana State Park, Turtle Bay, the Maʻakua Ridge Trail and World Famous Banzai Pipeline where you can catch a wave or watch pro surfers in...
Kona Studio + 2 Small Bonus Rooms, Big Covered Patio, Near Beaches /Airport
Newly renovated (June 2025)! Bright studio with Queen bed plus Full & Twin in bonus sleep rooms (76” ceilings). Perfect for families—kids get their own space at a fraction of hotel costs. Enjoy cool breezes at 1,070 ft elevation, a covered patio, and private...
Enjoy the Space! Super Pacific View, Kitchen Ease, Free WiFi–Waikīkī Shore #708
Unwind in this one-bedroom one-bathroom deluxe suite with views of the Pacific Ocean, which you can enjoy from your furnished lanai. This unit’s decor is reminiscent of iconic Waikīkī charm. You’ll love the wicker furnishings, wide-leaf paddle fan, and vibrant...
Boutique Hotel Waikiki FREE parking
Excellent Location, free parkingEnjoy a comfortable stay in this independently owned hotel room featuring a king-size bed, along with a twin-size pull-out for a third guest if needed, full bathroom, central AC, and a flat screen TV. The room includes a mini fridge,...
Diamond Head Grandeur: Kahala Luxury Villa with Ocean View
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.Find peace and tranquility in your very own...
Clean and Cozy Waikiki Condo, A Digital Nomad, and Surfer's Dream!
This stylish and cozy Waikiki Condo is located off Liliuokalani St. in the heart of Waikiki. 1 bedroom 1 bath on ground level, furnished with queen size bed in the bedroom and futon sofa in the living room, a/c in the bedroom. The building has a pool, Laundry room, and...
Luxury Lanikai Oceanfront Home – Secluded Beachside Elegance
LUXURY Lanikai oceanfront home built in 2006, charming board and batten home, concrete floors throughout with the charm of old Hawaii. Beautiful gardens, outside dining and entertainment areas, large pool, big yard spaces, and awesome private outdoor showers that you...
Monthly Discovery Bay 1403 1 Bedroom Ocean / Sunset / Marina / City Views Queen Bed, Sofa Bed
PANORAMIC OCEAN VIEWS, 5 Minute Walk to Beach, 1 Bed Room, Remodeled, Furnished and Fully Appointed. No smoking condo. Parking, Pool, Utilities, WIFI, BBQ, Gym, Security, Washer/Dryer Included. 1 Month Minimum / contact Agent.Ocean Views from High Rise, Tasteful and...
Executive Honolulu Home with Spectacular View
This 3 bedroom has it all! It is in a great neighborhood in Waialae Kahala. Newly renovated and furnished in a great neighborhood in Honolulu. Great View with 3 HD TV's with cable, free internet wifi, and a kitchen with granite counter tops and all the utensils you...
Upgraded Stunning Ocean View Studio w/Kitchenette, WiFi, A/C- Waikīkī Grand #716
Castle at Waikīkī Grand #716 - Charming and inviting are only two of the many words to describe this ocean view studio with a kitchenette! Wake up to the glow over the rim of Diamond Head Crater from your plush bed with two pillows. This studio provides ample space...
Perched at Pearl Harbor
Nestled atop a hill, our home offers an enchanting view of Pearl Harbor. Perfect for remote professionals and families alike, our property provides the perfect blend of comfort and scenic beauty.Welcome to our inviting home, where you can savor breathtaking Pearl Harbor...
Kailua Luxury Beachfront House
Prices start at $36,000/month and will not be pro-rated based on the length of stay. Please inquire for an accurate quote.Welcome to Kailua Beach Villa. This luxury beachfront home is perfect for your next Hawaiian vacation. This spacious 2 level home has 5 bedrooms (1...
Maluhia Beach House by Gather: Oceanfront Home w/ Lanai & 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 Maluhia Beach House By Gather – A...
Tranquil and Chic 1 Bd and Bth with Car and Sauna
"Tutu's Hale" a hidden tropical oasis in East Honolulu, features 1 bedroom and 1 bath, living room, kitchen, walk-in closet, outdoor patio space with hammock swings and furniture, with access to our shared dry sauna, cold plunge and outdoor shower. Those in need of...
Escape to Paradise! 2 Serene Units, Pool, 3 Restaurants, Right on Beach!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Ilikai Hotel Lite #1836: Studio Ocean View condo
**PROPERTY PROJECT**Ilikai Hotel Spalling and Exterior Painting ProjectAn exterior painting and spalling repair project to enhance the building’s structural integrity and appearance with minimal disruption will commence on August 18, 2025. Work Schedule: 9 AM – 5...
Ilikai Hotel One-Bedroom Unit. Perfect Ocean View. Fully Remodeled!
Come and relax in this renovated unit at the Ilikai Hotel. This spacious 1-bedroom condo has been making updates to make the space more comfortable and relaxing for travelers! This condo can comfortably sleep 4, with a California King bed and sofa sleeper in the living...
Kaimana Beach Hotel | Classic Queen | Beachfront Getaway
Tucked at the serene end of Waikiki, Kaimana Beach Hotel offers direct beachfront access, steps from Kapiolani Park and beneath Diamond Head. The Classic Queen is a cozy retreat with a plush bed and breezy island-inspired design. It's perfect for solo travelers or...