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.
Breathtaking Sunset Views and Perfect Backyard Pool and BBQ
House sits a right up the hill from downtown which makes for an amazing sunset. The property has a saltwater pool, patio and BBQ. Inside is fully furnished for a comfortable stay. The garage is remodeled and includes a ping pong table, corn hole, darts and full of beach...
Spacious 3BR/2.5BA Townhome in Quiet Ko Olina - Pool, Beaches & Golf Nearby
Escape to our cozy, peaceful 3-bedroom, 2.5-bath townhouse in the serene Hillside Villas at Ko Olina. Just minutes from world-class beaches, golf, and restaurants, our home offers the perfect blend of comfort and convenience for your tropical getaway. Nestled in a...
Ko Olina Beach Villas 608: Spacious 2BR Luxe Home w/ Ocean Views
Welcome to Ko Olina Beach Villas B608 by Gather, a spectacular sixth-floor beach villa in the serene Ko Olina Resort. This two-bedroom, two-bathroom oasis, with space for up to four guests, is a dream come true for those seeking a tranquil escape in paradise. From the...
🏖️Concierge Included | Ocean View | Walk to Beach! | Cental AC | vrKCV
vrKCV - Na Hale O Keauhou E6, Professionally Managed by Kona Coast VacationsEscape to paradise at Na Hale O Keauhou E6! Nestled in the serene and popular Na Hale O Keauhou complex, this townhome offers everything you need for a relaxing Hawaiian getaway. Just a short...
Waikiki Beachfront Rental (30 day min)
Fall asleep to lapping waves on a quiet corner of Waikiki in this beautiful modern haven. Located on the sought after 3rd floor of the famed Colony Surf on the Gold Coast end of Waikiki. Clean and modern remodel in 2018: all new cabinets, appliances, furniture and...
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...
Kona Hillside Estate - Gated Property with Lap Pool
Welcome to our family's private gated estate located on the beautiful hillside of Hualalai mountain in Kailua-Kona. We recently renovated our 4,000 SF home and enjoy hosting guests when we have availability since 2022.Guests will appreciate soaring ceilings, open living...
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...
Cozy 2-bedroom apartment in amazing Kailua-Kona with WiFi, AC
Discover this enchanting 2-bedroom gem in Kailua-Kona. This terrific apartment features a cozy living room with a sofa bed, a king bed, and two twin beds in the bedrooms. Enjoy a soothing bath in the bathtub and relax in the calming ambiance of this property. Experience...
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...
Tropical Acreage + Fruit Trees + Beach ~5m drive!
Welcome to "Pua Pono House," on Oahu's captivating North Shore, where country living meets relaxation, away from the hustle and bustle of Honolulu and touristy hotels. Nestled on a lush one-acre estate, our retreat offers a serene and secluded oasis. Centrally located...
Unique, Top of the Line Ocean View in Makaha
Locally owned and operated. Newly renovated with upcycled local accents and eco friendly products. All new premium wood cabinets combine with one of a kind solid cement coulter tops, stainless steel appliances, and mango wood shelving in the kitchen. A premium sofa...
Immersed in nature Home w/ A/C, bbq area, Hale Poola
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 five-bedroom, three-bathroom home sits in...
King Bedroom Beachfront Sans Souci 1104
You'll find bicycles, golfing, and more on site at this beach apartment. There's convenient covered onsite parking, so you can leave your vehicle behind and head out to Waikiki Beach and Kaimana Beach, just a short walk away. Relax on the porch or lanai (enjoy the...
Luxurious Ocean View Condo - Steps from the beach! nsleeps 6- 3 bedroom- 2 bath
Awaiting you in this tropical paradise is a luxurious 3 bedroom 2 bathroom 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...
Magic Sands Home, Steps From The Beach! Air Conditioned!
Welcome to this wonderful 3 bedroom / 2 bathroom duplex home only a 3 min walk from Magic Sands Beach. Just remodeled and professionally decorated, this charming vacation getaway has all of the comforts you desire in your home away from home, including air conditioning!...
Unforgettable Ko Olina 11th Floor Penthouse, Direct Ocean View
This ocean tower 11th floor two bedroom, two bath 1466 SF luxury Penthouse villa is located in Oahu's most prestigious beachfront destination - Beach Villas at Ko Olina ('Place of Joy'). You'll experience breathtaking panoramic ocean views from your private lanai while...
OCEAN FRONT Luxury Villa - Stunning Ocean Views - Steps To the Beach -Central AC
This is when QUALITY meets LOCATION!!! Impeccably maintained, built with only the best of the line in luxury, this Ocean Villa is located in arguably the best location on the North Shore and even in the world! Located at Turtle Bay Resort in the gated Ocean Villas...
Unique 8th Floor King bedroom condo Full kitchen Sleeps 3
Legally Permitted Rental - WAIKIKI GRAND HOTEL®815 One-bedroom Suite 2 Rooms in 1 Space1 King Bed1 Sofa BedFULL KITCHENGrab this one if it pops up for your dates! It is seldom available and often booked far in advance. Some years ago, a much-loved radio personality...
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...
Ko Olina Beach Villas O1006: Luxe Penthouse w/Pool, Golf, & Ocean Views
Welcome to Ko Olina Beach Villas O1006 by Gather, a stunning two-bedroom, two-bathroom tenth-floor penthouse with space for up to six guests in the exclusive Ocean Tower of Ko Olina Resort. This exquisite villa offers breathtaking ocean views, complemented by serene...
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...
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...
Kai Lani 14B by Gather: 3BR Resort Townhome w/ Pool & Spa
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 Kai Lani 14B by Gather, your...
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...
Waiulu Villa 119A – Bright & Updated | Includes Onsite Staff & Daily Housekeeping
Recently Updated! Located in the popular Waiulu Villa neighborhood, this luxurious 2 bedroom, 2 bath single-level lower floor corner villa was just updated with new furnishings and decor in the living room, dining room and lanai. Accommodating up to 4 guests, this light...
Lush Private Tropical Estate, Epic Views w/ Salt Water Pool & Spa
Nestled on an acre of private and quiet lush tropical grounds with heated pool and hot tub, Heart of Hualalai is your dream home, away from home, in Kona coffee country.Heart of Hualalai is a peaceful space where natural beauty and serenity meet mindful architectural...
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...
5★Resort like paradise, heated pool, ocean views, AC, peaceful gated community.
LOCATION LOCATION LOCATION!!! 3bed/3bath This tropical retreat home in the heart of Kona sits on a half acre lot surrounded by palm trees, lush green lawns and tropical flowers with gorgeous ocean and sunset views. This parcel has unobstructed ocean views and sits in...
Luxury Ko'Olina Coconut Plantation Oahu, 2-Story, 5 min to beach
Dream-like comfort awaits you and your family in this beautifully appointed 2-story, 1,700-square foot, 3 bedrooms, 2.5 bath townhouse vacation rental condominium in an award-winning residential resort community that offers privacy, relaxation, entertainment, and...
Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and Jacuzzi -Sleeps 8
IMPORTANT: Hawaii Senate Bill 1396 (SB1396) has been signed into law by Governor Josh Green. The legislation, signed on May 27, 2025, increases the state's transient accommodations tax (TAT) and introduces new fees to fund climate change mitigation and environmental...
Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage
HALE LANIKAILic# TA-161-257-7280-01Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations.Hale Lanikai is BACK! Better than ever!!All new furnishings throughout the property.Original Koa...
NEW LISTING Kailua-Kona 3-bedroom, 2-bath single-family home Ocean & Sunset View
Immerse yourself in the enchanting allure of Kailua-Kona at our 3-bedroom, 2-bath single-family haven, offering you panoramic views of the endless ocean horizon. Every detail has been meticulously attended to, including newly installed split AC units in every room, new...
Stunning Luxury Estate 🌺 Superb Private Lanai & Breathtaking Sunsets! 🌅 Keauhou Luxury Estate
Experience island lifestyle in one of Kona's most desirable gated communities: Keauhou Estates.Amazing home with 3 bedroom with 3 and 1/2 baths. Beautiful great room, dinning room and gourmet kitchen overlook the pool to the ocean beyond. Imagine a beverage and sunset...
119 night April disc Alii Dr Fully Equipped, Pool, Jacuzzi, BBQ, High-Speed WiFi
Welcome to Kona Bali Kai Ocean and Surf location! Your dream vacation awaits at our beautiful condo located in a prime spot close to downtown, Magic Sands Beach, and Kahalu'u Bay. Picture yourself opening the slider and listening to the soothing waves at night. Our...
Private Luxury Estate w/Pool, Jacuzzi, AC & Ocean Views: Ohana Le'ale'a
Step into the beauty of island life at Ohana le'ale'a, a newly built 3-bedroom, 3.5-bath luxury estate in Kona that blends expansive indoor-outdoor living with sweeping Pacific views. With 3,180 square feet of refined design, a private pool and spa, and a game room...
Just a couple houses away from the nicest beach on the island.
This rental is across the street from one of the nicest beaches on the island. Don't take our word for it check out the pictures of Waimanalo Beach and Bellows Beach. Kitchen has everything you need and opens up to a dinning table to enjoy your meals or you can take...
Spectacular View, Direct Oceanfront Kona, Top Floor
ALOHA, WE INVITE YOU TO RELAX AT SEA VILLAGEOur lovely top floor condo is perfect for you! Sit back and take in the spectacular view from the lanai as you watch dolphins and whales (in season) during the day and beautiful sunsets in the evening! Lose yourself in the...
Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach
Welcome to your tropical paradise getaway! This resort-like 5 bedroom home with swimming pool, hot tub, waterfalls, and stream is ideally located in a quiet cul-de-sac and offers the perfect blend of relaxation, comfort, and breathtaking ocean views. With Magic Sands...
Quaint Studio in Heart of Waikiki
With its outstanding location in the heart of Waikiki, this studio apartment offers a comfortable and convenient stay. Be steps away from the ocean, yet central to restaurants, shops, and amenities. The high floor offers partial ocean views, along with mountain view....
Newly Remodeled Kailua-Kona Condo w/ Pool Access
A trip to the Island of Hawaii is calling your name and this breezy 1-bedroom, 1-bathroom condo in Kailua-Kona is the answer! Located just a quick walk away from the beach, this vacation rental provides a fully equipped kitchen, an in-unit washer and dryer, and access...
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...
Stylish Waikiki 1 Bedroom Gem with Parking
30-Day Rental Only!Kick back, relax in this stylish, newly remodeled space in quiet Waikiki. Charming 1-bedroom apartment featuring fully-equipped modern kitchen and bathroom, and air-conditioned bedroom for restful nights. Perfect for solo travelers or couples with...
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...
Steps to Keauhou Bay! Great Water Access! Pool! Foosball table!
Beautiful home 120 steps from the warm waters of Keauhou Bay. House has 4 bedrooms, 2 1/2 baths and will comfortably sleep 8 in beds and up to 10 including futon couches. Fully equipped to give all the comforts of home while on holiday. Close to shopping, snorkeling...
Beautiful Condo Across the Street from Beach w/ Ocean View and Great Snorkeling!
Kahalu'u Beach Park is a prime spot for snorkeling, surfing and relaxing on the sandy beach. The beach is literally right walk across the street. Enjoy amazing ocean views from your private lanai, a spectacular infinity pool, hot tub and bbq area. This meticulous 2...
Makaha Shores Beach Front Ocean View Studio W/ AC
Makaha is a small town located on Oahu's West shore. 30 miles, 45 min from Honolulu Airport. The towns main attraction is its family friendly pristine and sandy beach. Makaha offers the best diving, snorkeling and surfing on the island. Our 5th floor gem beckons and...
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...
Kahala Beachfront Estate – Private Resort-Style Living
For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10 Night Minimum over the Christmas/New Years Holiday Season at $7,500 per night.Spacious beachfront estate is situated on lush tropical grounds, nestled in...
Makaha-465 Farrington: Spacious 4BR Oceanfront Haven with Modern 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.Escape to the enchanting shores of Oahu at...