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.
Beach Studio with private yard in Lanikai - 30 day Minimum Stay
Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east side of the island. Designed as your ultimate home away from home, this property offers a unique blend of seclusion and...
Coconut Plantation 1078-1: Bright 3BR Beach Home Steps from Ko Olina Attractions
Welcome to Coconut Plantation 1078-1, a spacious 3-bedroom, 3-bath townhome in the heart of Ko Olina Resort on Oahu’s sunny leeward coast. Offered exclusively as a monthly rental, this 1,548-square-foot retreat combines comfort, convenience, and the laid-back elegance...
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...
Dream Vacation at Ko Olina Hillside Villa (1498-8)
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...
3BR & Honeymoon Ocean Villas Getaway at Turtle Bay
This villa is a unique combination of our existing two villas; our 3-bedroom (VRBO 3722129) and our one-bedroom (VRBO 3722906) villas. These two units are separated by adjoining doors. We've chosen to add this listing, combining the two villas due to popular demand from...
Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset
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.Situated in the famed oceanside neighborhood...
Take-it-easy Waikīkī Beach Condo
Stay close to Waikīkī Beach, Kūhiō Beach Park and Kapiʻolani Park. Our newly-renovated 2-bedroom 2-bathroom beach pad is in a secure building with free parking. Highlights include a balcony with dining area, full kitchen, beach gear, kids accessories and a washing...
Ocean view Waikiki suite! Free parking, full kitchen, pool, close to beach!
Waikiki Banyan #3508-T1 – 201 Ohua Ave.NEW TO OUR INVENTORY! Enjoy your perfect Hawaiian getaway in this fully-furnished 1-bedroom/1-bath ocean view suite in the heart of Waikiki! 533 square-feet of interior living space, plus a private lanai with gorgeous views of...
Incredible Highrise Views! | Heart of Town
Enjoy breathtaking ocean views in this recently completely remodeled 1-bedroom hotel condo, perfectly located next to Ala Moana Mall and across from Ala Moana Beach Park. Ideal for up to 4 guests, the condo features two double beds, a functional kitchenette, and a...
🏖️Fully Air-Conditioned | Ocean View | Beautifully Renovated | vrKCV
vrKCV - Kona Isle B38, Professionally Managed by Kona Coast Vacations.Welcome to your oceanfront retreat in scenic Kailua-Kona! This renovated one-bedroom condo offers stunning ocean views and is located right at the water's edge, providing you with the perfect base for...
Sky Ala Moana 43rd fl PENTHOUSE Ocean & Diamond head view 1 Parking
-Luxurious Penthouse Retreat in the Heart of HonoluluIndulge in the ultimate urban oasis with our luxurious 43rd-floor penthouse condo, perfectly situated in the vibrant Ala Moana Center area between Waikiki and Kaka'ako. This prime location offers unparalleled...
Hualalai Haliipua Villa 104
Haliipua Villas are the newest generation of multi-family villas at Hualalai offering an array of designer finishes throughout the home. Special features include luxurious mahogany finishes, island-inspired ceiling treatments, enhanced lighting systems, built-in lanai...
KKSR#1202 DIRECT OCEANFRONT, 2ND FLOOR, REMODELED!, AMAZING VIEWS
Knutson & Associates is proud to be offering an incredible direct oceanfront unit in Building 1 at Keauhou Kona Surf & Racquet Club! A spectacular second story condominium that is oceanfront living at its finest. Enjoy Relaxation time on your incredible large lanai just...
Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course withnPool.
Serene, peaceful, and relaxing. This 3 bedroom, 2 bath single story home is located in Kailua-Kona, across the street from beautiful He'eia Bay (a one minute walk). The house sleeps 6 people and is stocked with most items needed for a relaxing convenient vacation. Most...
Oceanfront Beach Condo-Amazing views
Upscale Remodelled higher floor unit: High end appliances -Large side x side Stainless steel fridge (with ice maker) Stove / Large HE Front load washer and dryer. Good Quality Serta Queen Mattress / Patio furniture (high patio chairs and table to enjoy the view) New...
Honolulu Condo for Rent Steps to Kahala Beach
Ask owner about available dates/rates. The perfect studio for a couple on their Hawaiian get-away who want to live like locals during their stay. Please inquire about your specific dates and we can try to accommodate your stay. This beautiful and spacious studio with 1...
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...
Private Pool | Central AC | Concierge Included | vrKCV
vrKCV - Holua Kai 11, Professionalyl Managed by Kona Coast VacationsCharming 3-Bedroom Home with Private Pool in Holua KaiExperience the essence of Hawaiiana charm and grace in this unique three-bedroom, plus bonus room, three-bathroom home, designed with open space...
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...
NEW LISTING JULY 2023 Modern Renovated Condo - 1 block to beach, free parking!
See my other Properties # 1503692 and # 3197017 and #3156864 for more 5-STAR reviews and to book multiple units in the same building.Located on the 10th floor of the Waikiki Sunset with beautiful mountain and city views this condo offers enough beds to sleeps 6. 1...
Most Luxurious Ocean Front Condo in Kai Lani, Ko Olina, Hawaii
Awaiting you in this tropical paradise is a luxurious 2 bedroom, 2 bath condo that has everything you need to relax and enjoy your time in Hawaii. Nothing was spared in this fully equipped and fabulously appointed condo, whether it be to read a book in comfort and...
White Sands Village#206: Beachfront, Ocean Views, Elevator, No Stairs!
White Sands Village#206 is a spectacular addition to Knutson & Associates Vacation Rental Inventory. Welcome to the best location you can rent that's this close to the only major white sands beach in Kona! This premium unit is located on the 2nd floor & faces towards...
Breathtaking Studio Ocean Views! Pool! Beach!
Summary:🌺 Experience the Ultimate Hawaiian Retreat! 🌺Escape to paradise in this beautifully renovated high-floor unit offering breathtaking panoramic views of the Pacific Ocean, Diamond Head, and the vibrant Waikiki skyline. Whether you're here to relax 🌊 or...
CheCa Hale: Gorgeous Top Floor Corner Unit, With AC
Hopu i ka la ("catch the sun") at CheCa Hale! This airy, air conditioned, two-bedroom, two-bathroom corner penthouse is the perfect choice for family and friends traveling together. The home was beautifully and fully updated in 2022. Located in the beautiful Keauhou...
Dolphin House by Gather: North Shore Escape w/ Direct Beach Access
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 Dolphin House by Gather, a charming...
Spacious 3 Bed 2.5 Bath House in Kahakai Estates
Please note, effective Jan 1st. 2026, Hawaii`s Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
Tranquil Golf Course Townhome Ko Olina Kai Estates w/Great Amenities by Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to your luxurious retreat nestled within the exclusive Ko Olina Kai Golf Estates and Villas gated...
99 steps to quiet beach - Centrally located - Great for families & groups
Ideally located on iconic Alii Drive directly where the world famous Iron Man takes place annually. A number of palm trees and local landscaping on the front and side of the property add to the tropical appeal.Nearby are many of Kona's enviable attractions including its...
Updated 2-bed, 2-bath White Sands unit with ocean views, AC & modern amenities
Turn moments into memories at the iconic White Sand Village unit #301. This beautifully, fully-remodeled, and refurnished property is everything the luxury traveler is looking for. You have a front-row view of Magic Sands in this two-bedroom, two-bathroom corner unit...
★O‘ahu Perfect Vacation • Million Dollar Views, Pool, Near Beach, 4BR Sleeps 14★
Aloha! Welcome to Paradise Mahalo! Nestled in stunning mountains and ocean views, enjoy our modern, luxurious and cozy home located in the majestic Mākaha Valley. Whether it's a few rounds of golf, a hiking trails near by or a five minute drive down to the world famous...
Waiulu Tropical Sanctuary: A Luxury Oceanview Estate at Hualalai
Imagine waking in the primary suite of Waiulu Tropical Sanctuary, where collapsible walls vanish to reveal ocean breezes and poolside serenity—a magical start to your Hualalai escape. Masterfully redesigned by Henderson Design Group, this 4-bedroom estate, with a...
Newly renovated guest house with lush landscaping & gazebo
Honolulu HideawayOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the heart of Honolulu, this charming guest house offers a tranquil retreat surrounded by lush landscaping...
Hale Oka Nunu: Oceanfront Private, Spacious Paradise North Shore Home w/ Hot Tub
Hale Oka Nunu is a four-bedroom, three-bath oceanfront retreat on O’ahu’s North Shore, where the Pacific is just steps from your lanai. Designed for both relaxation and connection, this single-level home blends open living spaces, gourmet amenities, and sweeping...
Island Breeze Oasis - Newly Furnished
Welcome to our slice of paradise! Prepare for a vacation that feels like a dream – our villa is not just a place to stay; it's an experience waiting to unfold!Imagine waking up to the sun-kissed charm of four stunning lagoons right at your doorstep. These...
A perfect suite for temporary short term visitors
To our dear and faithful previous visitors and new vacationers Please always remember we NEVER charge an owner host fee - everything you see is yours to use, eat - candy, snacks, coffee, all beach and snorkel equipment etc etc etc. enjoy and of course no cleaning fee....
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...
Ilikai 30-Day Rental in Waikiki
This rental is on the 19th floor of the Ilikai Hotel with direct lagoon and ocean views. This 1 bedroom apartment has been remodeled into a large 500 sq ft studio and is gorgeous! High-end materials were used throughout the apartment. We used beautiful flooring in the...
Villa 315: Ocean views every bedroom!
Our Villa 315 is Located on the Turtle Bay Resort! You can use the Ocean Villas pool and Jacuzzi, park for free, and pay no resort fees! You can also use most of the Turtle Bay Resort Amenities for a fee. You have FREE access to the 12 miles of hiking and biking trails,...
3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY DISCOUNT!
E komo mai to Hale Makai, our piece of island paradise in Kailua. Beachside and just three houses from Kailua Beach - you are going to love it here.Lying alongside a fabulous three-mile stretch of protected beach, Kailua is a small town on the windward side of Oahu....
1 min walk to beach, New luxurious room with Ocean View!
Stunning ocean view, newly renovated and cozy bedroom, spacious living area and kitchen, with access ti rooftop pool, sauna...You and your loved ones will be close to everything when staying at this centrally-located place.Under 5 minute walk to:- 0.1 mi to Kalakaua...
Waikiki Banyan Upscale 1 BR
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...
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...
Get Away to Paradise
COVID Free Quaint 3 bedroom 2 1/2 Bathroom condo located in Ko' olina Fairways. Perfect place to unwind and relax. Two story with 3 bedrooms and two full bathrooms upstairs and kitchen, living room dining room and half bath downstairs. All the comforts of home to...
Live Aloha! Pacific View, Lanai and Laundry-Kanaloa<br>
Kanaloa at Kona #2203: Inside, you’ll find a bright living area with generous seating and a large flat screen television, perfect for entertaining your friends and family! The suite’s full size galley kitchen has Koa wood cabinetry, stainless steel appliances,...
5 Minutes to the Beach! Oahu Ocean View + Family retreat
☆ A luxury-style escape without the resort price ☆ Private 9-seat hot tub for relaxing soaks under the stars☆ Pool & Spa: Brand new Ocean-view community pool in a quiet, gated neighborhood☆ Outdoor Bar and grill in private backyard and 10-seat dining table for...
Ko Olina Beach Villas O905: 3BD Luxe Villa w/ Stunning Sunset Views
Immerse yourself in the luxury and beauty of Ko Olina Beach Villas O905 by Gather, a stunning villa perched on the ninth floor of the Ocean Tower, offering breathtaking views of the pool and ocean. This beautifully furnished three-bedroom, two-and-a-half-bath villa,...
Experience luxury at Hale Ola
Nestled in the heart of Kailua-Kona, this stunning vacation rental boasts the perfect blend of luxury, relaxation, and tranquility. This exceptional vacation rental offers a luxurious and tranquil escape with breathtaking ocean and coastline views, all set within a...
Aloha Breeze by AvantStay | Amazing Ocean Views, Game Room, Modern Design
Kick back in the heart of Makaha Valley at Aloha Breeze, a 4BR retreat that puts you 10 minutes from the beaches of Oahu. With a stunning view of tropical mountains and the ocean from your backyard, this modern Hawaiian escape blends style, space, and a beautiful...
Coconut Plantation by AvantStay | Resort Access, 0.4mi Walk to Beach!
Please note that this home is available for 28+ night stays only.Aloha from Coconut Plantation! Immerse yourself in the island lifestyle at this stunning two-story condo, surrounded by swaying palm trees and lush tropical landscaping. With 4 bedrooms and 3 full...
HOKU'EA HALE Oceanfront Private Home with Hot Tub
Welcome to Hoku'Ea Hale, a very private oceanfront residence featuring spectacular ocean views, ocean entry and abundance of covered outdoor living space. Every room opens to the outdoor ocean, where you'll experience tropical paradise and unparalleled views of the...