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.
Spectacular home with ocean views across the whole of the north shore.
Oceanview Paradise at Sunset BeachLocated on the majestic North Shore of Hawaii, this 3-bedroom, 3-bathroom retreat offers a slice of paradise with panoramic ocean views. Just a short stroll away from the world famous Sunset Beach, this home provides the quintessential...
Luxurious Ocean & Sunset Views Condo at Park Lane w/Luxury Building Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Park Lane is one of the most luxurious buildings in Honolulu! Located at the world famous Ala Moana...
🏖️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...
High Floor Luxury Oceanfront @ Waikiki Beach Tower
Waikiki Beach Tower Relax in this exclusive upper floor unit at the most luxurious vacation rental tower on the beach in Waikiki. This 1,200 SF newly renovated condo has the only open floor plan in the entire building and its sky high location on an upper floor provides...
Sweet & Cozy in Honolulu Free WIFI & AC
Discover this enchanting 1-bedroom gem in Honolulu. This tranquil apartment features 1 queen bed, WiFi, AC, a hair dryer, a washing machine, and an iron. The bathroom comes equipped with a hair dryer for your convenience. Immerse yourself in the peaceful ambiance of...
Includes Beach Gear! Kanaloa 303
Complimentary Late Check Out up to 7:00pm for stays of 5 nights or more between October 1-December 19, 2025 (stay must be complete by December 19th) based on availability at the time of booking. Please message us to inquire about the availability of late checkout on...
Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.
This is an absolute Oceanfront Villa. Watch the dolphins while you have breakfast.This wonderful Villa offers oceanfront amenities including the fragrance of the ocean spray and warm tropical breezes truly distinctive to Hawaii!Welcome to this two bedroom, two and...
🌴Immaculate, ocean view townhome offers quiet island living, located in Na Hale O Keauhou🌴
Immaculate ocean view townhome! Ocean views, epic sunsets and poolside afternoons: That's what a true Hawaii vacation is all about. This immaculate, three-bedroom townhome is set in the quiet, gated community of Na Hale O Keauhou just a mile from Kahaluu Beach, Kona...
Iconic Diamond Head and Ocean View in Waikiki!
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...
Ocean View! Lagoon Tower! Family Friendly Resort! Beautiful Hilton Condo On Waikiki Beach!
Set along the breezy coastline of Honolulu, and with all the comforts of home. You will have access to four swimming pools, one with multiple waterslides, a saltwater recreation lagoon, daily planned family activities, Waikiki Beach access, water sports, spa...
Trendy Hawaiian Monarch Studio | Ocean View | Pool
Relax in this beautifully renovated, modern studio at the Hawaiian Monarch building. Located at the beginning of Waikiki, this unit offers ac, smart tv, wifi and cable. It is a short walk from Fort DeRussy Beach Park, Hilton Hawaiian Village, Ala Wai Canal and more. The...
🏖️Ocean & Golf Course Views | 2 Bdrm with Loft | AC | vrKCV
vrKCV - Country Club Villas 334, Professionally Managed by Kona Coast VacationsWelcome to Country Club Villas #334 – Oceanview Golf Course Condo with Spectacular Sunsets! Experience the magic of island living at Country Club Villas #334, a beautifully remodeled...
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...
Kuilima West Estates 198B
Surf's up on the North Shore and our condo is the perfect place to Hang Ten! You'll appreciate the attention to detail, modern amenities and the chic, decor when you escape to our Surfer's Paradise. Our location provides easy access to the surrounding amenities, and we...
Seaside Splendor: Immerse Yourself in Luxury with this Stunning Oceanview Condo!
Oceanview bliss awaits! This condo not only boasts mesmerizing ocean views but also pampers you with luxury amenities. Enjoy a fully-equipped kitchen, spa-like bathroom, high-speed Wi-Fi, and beach equipment. Elevate your vacation - book this seaside sanctuary for the...
Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise
Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, deciding whether to go to...
Kailua Village#705 Top Floor, Gorgeous Remodeled 2 bedroom, in Heart of Town
Experience Paradise in This One of a Kind Stunning Two-Bedroom Penthouse in Downtown Kailua Kona, at the Famous Kailua Village. Escape to tropical bliss in this fully remodeled, top-floor(7th floor) penthouse located in the heart of Kailua Kona, Hawaii. With...
Gorgeous Lanikai Villa with Access to Secluded White Sand Beach
This gorgeous 5 bedroom, 4.5 bathroom, gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful arches...
!New Remodel Oceanview Waikiki AlaWai AlaMoana
New remodeled private, high rise studio in a secured apartment on Niu Street (Waikiki) with ocean view, Diamond head, city light, Ala Wai Canal view. Walking distance to Convention Center, Ala Moana, beaches, shops and eateries.Please inquire about other listings in...
Lulani House Beachfront Vacation Home in Haleiwa
Imagine walking out the back gate of your beachfront vacation home, entering a private path with tropical trees overhead and white sand beneath your toes. Then you see it, the turquoise blue water, waves, rays, and views of Three Tables Beach that you and your loved...
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...
Seaside Retreat Condo
Welcome to your retreat by the sea. A great ocean view Overlooking Kahaluu Reef Bay. AC & centrally located in the heart of Kailua-Kona right on Ali'i Drive. Free Digital guide with booking with lots of local recommendations. Designed for comfort and thoughtful details....
North Shore Villa - Relaxed Luxury Retreat
Welcome to your peaceful retreat on Oahu's stunning North Shore, located in the desirable Kuilima East community. Nestled next to the luxurious Ritz-Carlton Oahu, Turtle Bay, and overlooking its world-renowned golf course, this charming vacation rental offers the...
Relax, with breathtaking ocean views. Makaha 1-bedroom condo near Ko Olina
Nestled in the town of Makaha, our 1-bedroom condo offers a tranquil retreat for your Hawaiian getaway. As you step inside, you'll be greeted by a gorgeous ocean view! A kitchenette, complete with a stove, oven, refrigerator, and all the necessary appliances and...
Stunning Ocean View Luxury Suite - Ko Olina Beach Villas O421 End Unit
Escape to paradise at our luxurious 2-bedroom, 2-bathroom ocean view villa in the heart of Ko Olina Resort, Oahu’s sunny west shore. Nestled steps from four turquoise lagoons, this professionally designed condo offers breathtaking Pacific Ocean views and the perfect...
A Slice of Paradise in Kona - walk to stores, restaurants and the beach
Nestled in the center of Kona this 1BR/1BA recently fully renovated condo offers a base for 2 to 4 people as you seek local attractions or nearby restaurants. Many stores as well as the beach are in walking distance. Yearning a home cooked meal, use the fully equipped...
White Sands Village#121: Beachfront Complex, AC, Spacious Unit!
Escape to Paradise at White Sands Village in Kailua Kona! Unit#121 has all the essentials one needs for a Beachfront Vacation. Welcome to your perfect Hawaiian getaway! Nestled in the heart of Kailua Kona, this 2-bedroom, 2-bathroom unit at White Sands Village offers a...
Modern Suite / Free Parking / View / AC / King Bed / Kitchen / Prime Location
Modern Suite in the Heart of Honolulu – Walk to Waikiki Beach.Our modern suite is located in the vibrant heart of Honolulu, just a 10-minute walk from the iconic Waikiki Beach. Enjoy the best beaches, dining, nightlife, and shopping Honolulu has to offer, all within...
Beautiful Marina Sunset Views, Located In The Ilikai Hotel!
This condo is located on the 9th floor of the Ilikai Hotel. You'll have amazing views of the Ala Wai Yacht Harbor and Ala Moana Beach Park, with stunning sunset view. KITCHEN- Refrigerator- Cooktop/Oven- Microwave- Dishwasher- Dinnerware, Glassware, Silverware,...
2Bd/2Ba Townhouse with full kitchen steps away from ocean
End unit townhouse with 2 bedrooms/ 2 bathrooms located in the gated community of Keauhou Kona Surf and Racquet club. Downstairs you will find full size kitchen with granite countertops, living room with large 55 inch Samsung TV with 200 MBPS internet and a full...
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...
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...
Beautiful Mountain Views & Steps to Waikiki Beach
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...
Luxury North Shore Beachfront - contact for details HI requires 1 renter/30 days
Nalu Hale is a luxurious 5 bedroom+, 6 bathroom, 5 star quality home located on the famous North Shore, Oahu. See IG name below, so you can see our profile. PLEASE CONTACT FOR CLARITY ON HAWAII REQUIREMENTS FOR ONLY 1 RENTER PER 30-DAY PERIOD TO ENSURE CLARITY ON WHAT...
Turtle Bay Villa G318
Welcome to Villa 318, one of the most spacious and luxurious properties at Ocean Villas and Turtle Bay. Nestled on Oahu's stunning North Shore, this tropical retreat is the ideal escape for families looking to relax and enjoy a slice of paradise. We look forward to...
Kahikole Villa: Hualalai Resort Remodeled Villa with Pool & Spa
*Newly Remodeled*Kahikole 4 bedroom Luxury Villa on the 8th fairway of the Nicklaus designed Hualalai Golf Course. Incredible views over the 8th and 4th greens, ocean views and sunsets.Kahikole Villa offers 3 bedrooms in the main living area with two outdoor shower...
"Pupukea Perch," Oceanfront Views, Walk to Beaches
Oceanfront with sweeping views of surfers, whales, and sunsets. This 3-bedroom retreat sits within a marine sanctuary, offering rare privacy and walking distance to three iconic beaches, world-class snorkeling, local eats, grocery. Endless North Shore adventures just...
Fabulous Waterfront Modern Home on the Keiki Beach, Walking Distance to Town
E komo mai! Welcome to our light and bright beach house, located directly on the calm and lovely Keiki Pond at Kona Bay Estates. Enjoy ocean and beach views from every room. The primary bedroom features 180* view of the beautiful Kona coast. Kona Bay Estates is ideally...
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...
Beautiful conveniently located 2-bedroom ocean view home in Kailua-Kona.
Beautiful and peaceful two bedroom home with an ocean view and convenient location. Located 7 minutes from the airport and 5 miles from town. Easy access to beaches, grocery stores, and everything Kona has to offer. This two bedroom space is the second floor of a...
Lush Oceanview Villa w/Hot Tub & AC - Fairwayfront at Hualalai: 3101 Kumukehu
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...
Hualalai Palm Villa 140C
The spacious floor plan includes a downstairs primary bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and golf course. Guests enjoy...
Waikiki GoldCoast spectacular views ocean, sunsets, surfers!
Spectacular high floor unit, stunning panoramic views of Waikiki, sunsets, surfers, Diamond Head, and Friday night fireworks. Beautiful 1 bedroom oceanfront condo with easy Waikiki Gold Coast living is located in the Diamond Head Beach Hotel & Residences, right on the...
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...
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....
Tropical & inviting home w/spa, torches, waterfalls & ocean view
Hale Wailele (Waterfall House) is a beautiful, spacious home with floor to ceiling windows in the great room looking out onto fountains in the pool with an incredible ocean view beyond the palm trees and torches. The architecture of the home makes it unique and inviting...
2 Bed 2 Bath Surfing & Snorkeling in Kahaluu Bay
Aloha! Come and stay at the Hale Hamoa created for everyone with everything we love about Hawaii. Only 1 minute walk to one of the best snorkel beaches on Kona Side and the Surf school next door. The condo comes with all the essentials you need for an awesome vacation...
Gorgeous remodeled condo Oceanfront! SUNSET! <br>
Elegance on a budget! This quiet third floor end unit has spectacular ocean views from throughout the condo. Our air-conditioned condo overlooks the beautifully manicured grounds with unobstructed ocean views. The kitchen has concrete countertops and top-end appliances....
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Beautiful 2bedroom / 2bath home overlooking Kailua Bay in the heart of downtown Kona, HI. Conveniently located on the gentle slopes of Hualalai. Escape the heat with cool breezes in a tropical landscape setting. Nearby shopping, dining, and entertainment. Fully stocked...
Ko Olina Beach Villas O1402: Spectacular 14th Floor Penthouse w/Ocean Views
Welcome to Ko Olina Beach Villas O1402 by Gather, a stunning penthouse on the 14th floor where luxury meets comfort in a tropical paradise. This three-bedroom, two-and-a-half-bathroom penthouse villa accommodates up to six guests.As you enter, the peaceful Pacific...