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.
^Marriott's Ko Olina Beach Club^ - 1BR 1BA MT. VIEW ^INSTANT BOOKING^ 1 car free
Marriott's Ko Olina Beach Club - 1BR 1BA MT. VIEW FULL resort access***INSTANT BOOKING***1st car park for free ($45 a day value)Full access to the resort’s services and amenities are included with every reservation.3 nights stay checking in on 3/11/2025 is for Ocean...
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...
Villa Olina Charming 3-Bedroom Villa On the Golf Course Steps Away from Lagoons
Beautiful & spacious yet cozy and comfy Ko Olina Kai Welcome to your tropical haven in the coveted Ko Olina Kai community. This delightful 3-bedroom, 3-bathroom house rental offers a prime location just a 10-minute walk from the stunning Ko Olina Lagoons. Tailored for...
Side by side penthouse suites with Central Air and unencumbered Ocean Views
* Penthouse enjoys the best location at the Kona Coast Resort, and is situated steps away from the Kona Coast Resort’s main pool, large jetted spa, restaurant, exercise facility, check-in office, and concierge activities desk.*Penthouse consists of TWO one-bedroom...
Cool retreat at the entrance to Lanikai. Very Close to Beach. 3 Primary Bedrooms
Live your best life! An opportunity for beach living in this renovated and updated luxury rental with views of Kailua Beach and Kailua Beach Park - it's brilliant turquoise blue ocean, sandy beach, large grassy areas and tall ironwood trees. Fine craftsmanship abounds...
Fabulous Kona Reef Resort Ocean Front - Penthouse Floor - 2 BR/2 BA Condo
This fully air-conditioned beautiful oceanfront corner unit is less than 30 feet from the water's edge. Enjoy spectacular sunsets from your large lanai, watch the surfers, para-sailers, boogie boarders, playful dolphins, turtles, whales and passing cruise ships.Fall...
*Newly Renovated Oceanfront Waikiki- Ilikai Marina
*Exciting Updates in Progress!We’re currently renovating to make your stay even better. In the meantime, please take a look at our beautifully updated Ilikai Marina listing to see the stunning upgrades you can expect soon!We’re excited to share our top picks for...
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
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.Hale Ohana meaning Family House is just that!...
Unique Corner Studio Condo Incredible Ocean and Canal Views!
About this space Your Ideal Vacation Stay Here! The view is awesome from this newly remodeled, spacious studio condo on the 27th Floor of the Hawaiian Monarch Hotel, just a few blocks from Waikiki Beach! This clean, modern, luxurious space is in a great location to...
Beautiful Ocean-view Kailua-Kona Condo! 5 min walk to the beach!
Enjoy an amazing experience at our centrally-located place. Our ocean-view condo is a 5 minute walk to the beach and an 8 minute walk to downtown Kona, where you will find awesome restaurants, bars, shops, the farmers market, churches, a great atmosphere and...
Majestic Mahakea – Oceanfront Oasis on Oahu's North Shore
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 Majestic Mahakea: Oceanfront Oasis...
Ocean-view condo with lanai, shared pool, hot tub, fitness center & bbq area
Na Hale O Keauhou H5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched in one of Kona's premier resort developments, Na Hale O Keauhou, this spacious 2-bedroom, 2-1/2 bath,...
Breathtaking View on Beautiful Sandy Beach Oceanfront
This Oceanfront Condo has an amazing view. It has a gorgeous Great Room and a beautiful fully equipped kitchen. With the roar of the ocean just a few yards away, you will not want to leave the Lanai after relaxing on the Tropitone furniture.This Condo has a beautiful...
OCEANFRONT. Amazing views of dolphins and sunsets. Newly renovated. No stairs.
RIGHT ON THE WATER in one of Kailua-Kona's most sought after complexes! This open and spacious, 2-bedroom condo has a spectacular, 180-degree, Kona coastline and ocean view. From the private lanai, watch spinner dolphins as you savor your morning Kona coffee. Later,...
Three Bedroom Villa at The Beach Villas at Ko' Olina
* Book with confidence! This vacation rental is a LEGAL Oahu vacation Rental Operating in a Resort Zoned District and is not affected by passage of Bill 89. This Luxury Condo is a spacious and beautiful 3 bedroom, 3 bath, professionally decorated Villa with a beautiful...
FOUR PADDLE Mountain view with full kitchen, AC, washer/dryer, Wi-Fi, parking
Four Paddle #2311 – 2140 Kuhio Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Located on the cool side of the building, you'll enjoy lovely Ala Wai Canal and Ko'olau Mountain views from this well-equipped 23rd floor one-bedroom condo (553 sqft...
Kailua Condo / Townhouse on Oahu 7 day per 30 day period
”Aloha and Welcome Home" message me on availability as it can only be rented once in a 30 day period. Ordinance 19-18 does not require a renter to physically occupy a rental property for any minimum length of time. Remodeled 2x bedroom 2x bathroom condo / townhouse....
Poolside Waikiki Retreat w/ AC, surfboard storage, walking distance to beach!
Located in the center of Waikiki with amenities like A/C, on premises laundry, and bike & surfboard storage, this spot is a no brainer. Directly across from the *eight foot deep* outdoor pool and patio, and just blocks from the beach, this apartment is truly a piece of...
Spacious Modern 2Bdrm Condo, Free Parking in Bldg., Full Kitchen, Sleeps 6.
Renovations were completed in March 2024. Everything is new. 6 can sleep comfortably, 7 when 1 or more are children.This condo is tastefully decorated and features a spacious living room with a comfortable sofa that opens to a full-sized bed, and a flat-screen TV. The...
Lily's Kona Hideaway-Oceanfront & AC on Demand
Welcome to your Hawaiian paradise! This renovated second-floor condo at Kona Isle blends modern luxury with island serenity. Bright, open spaces and upscale comforts await. Enjoy a solar-heated pool, oceanfront BBQ, and lounge with spectacular sunset views. Soak in the...
Modern bungalow with lanai, grill & outdoor shower - steps to Keauhou Bay
The ShackOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hawaii is calling- answer with this laid-back island bungalow. Just a step from Keauhou Bay and shopping center, this...
Designer Hali'ipua Sunset Sanctuary ~ Hualalai ~ Fire Pit, Personal Concierge
Step into a world of refined beauty at Hali’ipua Sunset Sanctuary, where every detail of the stunning contemporary design—crafted in serene neutral hues—invites you to unwind in luxury. Picture sipping coffee, surrounded by original artwork and custom furnishings,...
Kona Makai Building #1
Stunning ocean views from the lanai, ocean front from the bedroom, the sounds of the surf on the rocks, and the spirit of Aloha welcomes you to our home in Hawaii. Kona Makai is a beautiful oceanfront complex with well maintained gardens, swimming pool, hot tub, gas...
Island Glow Kailua Village, AC and ocean views in the heart of Kailua Kona
See whales, dolphins, Ironman Village and Ali’i drive from your very own lanai! Island Glow in Kailua Village is a beautifully remodeled 1 bed 1 bath condo with a brand new king bed and queen pullout sofa bed in the heart of historic Kailua Village. You will enjoy...
Luxurious High floor Waikiki Landmark Condo, Ocean & Diamond Head views!
Waikiki Landmark is Waikiki's premier condominium, located at the Gateway to Waikiki. The contemporary architecture reflects a pair of triangular towers, the Makai Tower (ocean) and Mauka Tower (mountain) this two bedroom unit is located on the Makai Tower and is...
Kona Palm House 3 Bed/2.5 Ba with Pool
The Kona Palm House has a total of 3 bedrooms and 2.5 bathrooms. The Master with Cal King bed is located upstairs with an en suite bathroom and walk in closet. The half bathroom is located next to the kitchen at the top of the stairs. Also, upstairs you will find a...
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
Do you like an unobstructed panoramic view of the ocean and sunsets? Comfortable beds? Air conditioning in 4 zones? Quiet neighborhood? Excellent location in the heart of Kona? Free WiFi? This house has it all. Wake up in the morning and have a coffee on the very large...
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...
Kuilima East Condo
Permit # 2212-CCH-0655Aloha!This legal non-smoking unit is located at Kui'lima East Condo's at Turtle Bay Resort on the famous North Shore of Oahu. Situated next to the 17th hole of the Fazio course, this spacious 820 square foot one bedroom, two full-bath unit has...
Direct Oceanfront - Magic Sands Beach!
Unit recently remodeled - new portable air conditioner, brand new appliances, flooring, furniture, linen, towels, and full size hot water heater!This gem is literally a few steps from the Ocean. It faces West, which allows you to see amazing sunsets every evening. Relax...
Luxurious Condo on Ali’i Drive with Ocean view.
Complete your visit to the islands by staying in this Samoan-inspired 3-bedroom, 2-bathroom condo at Ali'i Cove. Featuring Polynesian interior design, the vibrant color scheme warms your spirits, setting in the reality that you are truly in paradise.Sip a freshly brewed...
Fairways Ko Olina 27H: Your Ultimate 3BR Retreat in Hawaii with Resort 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.Step into paradise with a stay at Fairways at...
Honu Hale Waikiki: 2BDR Spacious Panoramic View
Experience a unique Hawaiian getaway in our 2BD/2BA spacious condo in the heart of Honolulu. Enjoy stunning panoramic city and ocean views through floor-to-ceiling windows and relax on two private lanais. With ensuite bathrooms, a fully-equipped kitchen, and modern...
FOUR SEASONS RESORT "HUALALAI HALE”, MODERN LUXE RETREAT, OCEAN VIEW, 1.5 ACRES.
Hualalai Hale: Your Luxe Private 4-Bedroom/4.5-Bath, Hualalai Resort Retreat, Tropical Landscape, expansive yard, Big Island HawaiiWelcome to Hualalai Hale—Your personal luxury resort home nestled within the exclusive and gated Four Seasons Resort Hualalai on...
Waikoloa Fairways #A310: Top Floor,Breathtaking Lake, Golf Course&Ocean Views
VIEWS, VIEWS, VIEWS!! This gorgeous condominium has the WOW Factor when you go to the Lanai. Absolutely Breathtaking views over the Golf Course that sweep to the Ocean over the Kohala Coast and to Maui, make this condominium a truly special property.The location, views,...
Famous Waikiki Beach Tower 2BR 2B Ocean View!
Summary:Located in the heart of Waikiki, this 2 Bed 2 Bath Luxury Oceanfront Suite is located in the Aston Waikiki Beach Tower Hotel! This property features floor to ceiling windows which open to a large private balcony that overlooks Waikiki beach and the Pacific...
Keauhou Gardens - Top Floor Hideaway
Spacious top floor condo offering a nearly 180 degree ocean view from a large private lanai overlooking a free form pool and spa tub with lava waterfall.This roomy 1600 square foot unit is newly air conditioned and features a condo wide glass wall opening the generous...
Ocean Front! Stunning Remodel in 2024! 102 Kona Riviera
Ocean Front Stunning Remodel in 2024Kona Riviera #102Bedroom Configuration:Master Bedroom: King Bed Living Room: Sleeper SofaAmenities:Beach Equipment: All of our vacation rentals include beach towels for the maximum occupancy, four beach chairs, two boogie boards, one...
Turtle Bay Hale Lani by RedAwning
This lovely 1 bedroom w/loft upgraded unit has new kitchen cabinets &appliances, ceramic tile floors and granite countertops. The living room has aflat-screen TV, internet and WIFI, and ceiling fan. Window a/c in the livingroom and the bedroom. Reserved parking spot,...
Ocean View Sky Ala Moana Condo w/Amazing Amenities Near Restaurants & Shops
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 The Sky Ala Moana, the newest pinnacle of luxury in Honolulu. This exquisite property,...
Ko Olina Beach Villas B506 by Gather: Luxury 2BD 2BTH w/ Ocean Views
Welcome to Ko Olina Beach Villas B506 by Gather, an elegant two-bedroom, two-bathroom villa located on the fifth floor of the renowned Ko Olina Resort. With space for up to six guests, this stunning vacation retreat offers a blend of luxury and island charm, making it...
Modern Luxury 2bed 2bath with Ocean Views and Easy Parking
Great care was taken in creating this comfortable, practical, and modern luxury home with ocean views from every room. Materials, colors and features uncommon in a rental were thoughtfully combined to create a unique, calm environment for relaxing. This is living well...
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...
Waikiki Shore 2 Bedroom Condo
Welcome to our 2 bedroom Waikiki Shore Condo. This exclusive Waikiki Shore Condominium is located directly on Waikiki Beach, and is the only privately owned condominium building on Waikiki Beach, and sharing this world famous beach frontage along with some of the finest...
Charming Dolphin Suite with AC in delightful Kailua
Consider this studio your home away from home while you visit Kailua. We hope you enjoy what our place and Kailua has to offer.NOTE: Temporary construction site is nearby so price has been reduced. Details provided upon booking request so you can make a decision if this...
Waikiki Banyan 1BR Corner Unit, Gorgeous Mountain/DiamondHead view, free parking
Aloha E Komo Mai. Welcome to Waikiki Banyan Rental, our vacation rental condo at the Waikiki Banyan.Our unit is a LEGAL short term vacation rental at the Waikiki Banyan. (Registered with the C&C of Honolulu, Permit # 2212-CCH-0749).The Waikiki Banyan is one of Waikiki's...
OCEANFRONT, Stunning Corner Unit in Boutique Complex, Spacious, Pool, A/C!
Right-on-the-ocean, newly renovated, upscale and spacious condo in a gated boutique complex. Top floor (second floor) large 700 sq foot corner unit with nobody above you. Unbelievable views from the lanai and living room. Windows everywhere that will make you feel like...
Luxury beachfront villa on a world class beach in Kailua, HI
As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.This luxurious Kailua Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises...
Hawaiian Style Escape – Pools, Water Activities, Golf, Shops, & Dining Nearby
Experience the Keauhou Resort Community: Your Hawaiian Escape in Kailua-KonaWelcome to our charming 1-bedroom, 2-bath condo in the beautiful Kanaloa complex. The cozy bedroom features a luxurious king bed, and the living room includes a convenient queen size Murphy bed...
Kulanakauhale 3558: Lavish Oceanview Estate, Private Pool & Spa at Hualalai
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...