Oahu Vacation Rentals

Oahu Vacation Rentals in Hawaii!

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These Oahu vacation homes, condos, villas, cabins, cottages, chalets, and bed & breakfasts are presented by their owners or agents. Please contact them directly with your inquiries. Click on the underlined descriptions below for more details and property photos.
Click Here to review listings ordered by city and # of bedrooms.
 
Premium Listings
Real Hawaii SPECIAL RATES - Ka'a'wa- Weddings, reunions Welcome! DEALS ON OPEN DATES
  • Windward
  • Villa
  • 3-10 bedrooms, sleeps 6-21
  • 2-7 bathrooms
  • Weekly rates
    From 6000 to 10000 USD
 

Spa Oceanfront Private Home - 3 Lg OceanFront Decks - Wonderful Views! Private: you're the only occupants! starting $195/night
  • North Shore
  • House (single)
  • 2 bedrooms, sleeps 6
  • 1 bathrooms
     

    5-Acre - Beachside - Hideaway VILLA - Mokuleia
    • Mokuleia
    • House (single)
    • 6 bedrooms, sleeps 18
    • 4.5 bathrooms
    • Weekly rates
      From 6000 to 9500 USD
     

    Spectacular, North Shore, Ke Iki Beach House! The View, Beach and Setting Is Unbeatable!!
    • Haleiwa
    • Beach House
    • 3 bedrooms, sleeps 8
    • 2 bathrooms
       

      North Shore Beachfront Vacation Home
      • North Shore
      • House (single)
      • 5 bedrooms, sleeps 18
      • 3.5 bathrooms
         

        Affordable Beach-Front Condo --Completely Renovated!!
        • Makaha
        • Condo
        • 1 bedrooms
        • 1 bathrooms
           

          High Styled Hawaiian Elegance Situated Next to Hanama Bay. Waikiki Luxury Vacation Home Rental
          • South Shore
          • House (single)
          • 4 bedrooms, sleeps 8
          • 2.75 bathrooms
          • Weekly rates
            From 4800 to 9100 USD
           

          Hale Nanea "House of Relaxation" is a 4+ bedroom, 5.5 bath luxury villa! Located in one of the most prestigious areas in Hawaii.
          • Diamond Head
          • House (single)
          • 4 bedrooms, sleeps 10
          • 5.5 bathrooms
             

            Oceanfront Beach House - Tropical Paradise!
            • Haleiwa
            • House (multifamily)
            • 3-7 bedrooms, sleeps 1-16
            • 1-4 bathrooms
            • Weekly rates
              From 1750 to 1995 USD
             

            Beautiful 2-Bedroom Vacation Rental in Hawaii
            • Kailua
            • Condo
            • 2 bedrooms, sleeps 6
            • 2 bathrooms
               

              Luxurious & Safe "Sunset Beach" Home Away from Home
              • Sunset Beach
              • House (multifamily)
              • 6 bedrooms, sleeps 15
              • 4 bathrooms
              • Weekly rates
                From 3000 to 4000 USD
               

              Exclusive Ko Olina Resort of Oahu - 2 Villas Side by Side Available..
              • Ko Olina
              • Villa
              • 3 bedrooms, sleeps 1-14
              • 2.5 bathrooms
                 

                Honolulu, Hawaii - Oceanfront Oasis - with Pool & Jacuzzi
                • Honolulu
                • House (single)
                • 6 bedrooms, sleeps 10-12
                • 7 bathrooms
                   

                  "North Shore Oasis" Beach Front - Oahu
                  • Mokuleia
                  • House (single)
                  • 4 bedrooms
                  • 2 bathrooms
                     

                    Kailua Beach House
                    • Honolulu
                    • House (single)
                    • 6 bedrooms, sleeps 12
                    • 5 bathrooms
                       

                      Affordable Family Lodging at Fabulous Turtle Bay!
                      • Kahuku
                      • Townhouse
                      • 2 bedrooms, sleeps 2-6
                      • 2 bathrooms
                      • Weekly rates
                        From 800 to 1150 USD
                       

                      GORGEOUS WAIKIKI 1BEDROOM +1 DEN/BEDROOM, 2 BATH CONDO W/ SPECTACULAR DIAMOND AND OCEAN VIEWS - WALK TO BEACH!!
                      • Honolulu
                      • Condo
                      • 1 bedrooms, sleeps 3
                      • 2 bathrooms
                         

                        Luxurious Beachfront Oasis - Once Owned by John Travolta - Extreme Privacy with Swimming Pool & Jacuzzi
                        • Honolulu
                        • House (single)
                        • 3 bedrooms, sleeps 8-10
                        • 3 bathrooms
                           

                          SPECIAL offers on Gated Home On Sandy Sunset Beach!
                          • North Shore
                          • 2 homes
                          • 3 + bedrooms, sleeps 2-10
                          • 2.5 bathrooms
                          • Weekly rates
                            From 1950 to 2600 USD
                           

                           
                           
                          Rental Locations(Listed alphabetically by City or Town)
                           
                           
                            City BR(s) BA(s) Sleeps Description
                           
                          Diamond Head0-studio BR1 BA2Lani Lanai; Affordable Oahu Luxury Vacation Condo
                           
                          Diamond Head1 BR1 BA2Makapu'u Suite - Diamond Head Beach Hotel and Residences on the Gold Coast
                           
                          Diamond Head1 BR1 BA2Kahakai Penthouse - The Diamond Head Beach Hotel
                           
                          Diamond Head1 BR1 BAKuuipo Suite - Diamond Head Condo
                           
                          Diamond Head1 BR1 BA2Nani Luna Suite - One of a Kind Beachfront Oasis - Diamond Head
                           
                          Diamond Head1 BR1 BA4Magnificent Gold Coast Condo - "The Leilani Suite" - Diamond Head
                           
                          Diamond Head1 BR1 BA4TOP OF THE LINE IN OCEANFRONT CONDO LIFESTYLES IN HAWAII
                           
                          Diamond Head2 BR2.5 BA6+Majestic Diamond Head Estate - In one of the Most Prestigious Neighborhoods on the South Shore of Oahu
                           
                          Diamond Head2 BR1 BA5Diamond Head Beach Hotel - DELA301DHBH - Exclusive HIBISCUS SUITE
                           
                          Diamond Head2 BR1 BA4-6The Rainbow Penthouse; Luxurious Condo with Forever Views - Oahu
                           
                          Diamond Head2 BR1 BA4Luxury Ocean Front Condominium - The Oahu Suite
                           
                          Diamond Head3 BR3.5 BA6-8Oceanfront Diamond Head Estate - Oahu
                           
                          Diamond Head3 BR2.5 BA6+HIBISCUS PLACE VILLA WITH SWEEPING OCEAN VIEWS - DIAMOND HEAD
                           
                          Diamond Head4 BR5.5 BA8Exquisite Beachfront Estate with Panoramic Ocean Views
                           
                          Diamond Head4 BR5.5 BA10Hale Nanea "House of Relaxation" is a 4+ bedroom, 5.5 bath luxury villa! Located in one of the most prestigious areas in Hawaii.
                           
                          Diamond Head5 BR5.5 BA10#125 Diamond by the Sea
                           
                          Ewa Beach3 + 3 BR1.5 + 1.5 BA2-6-12Oceanfront /Beach Duplex W/ Diamond Head and Waikiki Views / Tidepools
                           
                          Ewa Beach4 BR3 BA10Executive, Elegant, and Exclusive Ewa Beach Home - Island Paradise
                           
                          Haleiwa1 BR1 BAElegant Studio - Hale'iwa, Oahu - Hawaii
                           
                          Haleiwa1 BR2 BA4Haleiwa Town - Beachfront!
                           
                          Haleiwa1-4 BR1-3 BA2-8Steps from Waimea Bay & Beach! From $125/nt - $800/wk US Dollars
                           
                          Haleiwa1+ BR2 BA2-4Beach Front Haleiwa on North Shore Oahu: ;
                           
                          Haleiwa2 BR1 BA2-4KaHaleO'olina in Beautiful Haleiwa, Oahu
                           
                          Haleiwa2 BR1 BA4Hale'iwa - The Surfing Capital of the World !
                           
                          Haleiwa3 BR1 BA8"Waimea" Our Large Ocean View Home - in Haleiwa, Oahu
                           
                          Haleiwa3 BR2 BA6North Shore Beachside Cottage - Breathtaking Views
                           
                          Haleiwa3-7 BR1-4 BA1-16Oceanfront Beach House - Tropical Paradise!
                           
                          Haleiwa3 BR2 BA8Spectacular, North Shore, Ke Iki Beach House! The View, Beach and Setting Is Unbeatable!!
                           
                          Haleiwa5 BR3 BASurfers Paradise - Have the Run of the House - Haleiwa, Hawaii
                           
                          Hawaii Kai3 BR3 BA6-8Huge Waterfront Home in Hawaii Kai-like a Private Resort, within steps from the Crystal Blue Ocean
                           
                          Hawaii Kai3 BR3 BA12Secrets Beach House; a tropical, very private 1/2 acre estate with gas tiki torches, saltwater pool & spa
                           
                          Hawaii Kai3 BR2 BA6-8Private Waterfront Hawaii Kai Home
                           
                          Hawaii Kai4 BR3 BA10Hawaii Kai - 4 Bedroom · 3 Bath· Executive Home - 520 Lunalilo Home Rd
                           
                          Honolulu1 BR1 BA2-4Canal House Jewel
                           
                          Honolulu1 BR1 BA1-4Old Waikiki
                           
                          Honolulu1 BR2 BA3GORGEOUS WAIKIKI 1BEDROOM +1 DEN/BEDROOM, 2 BATH CONDO W/ SPECTACULAR DIAMOND AND OCEAN VIEWS - WALK TO BEACH!!
                           
                          Honolulu1 BR1 BA4Located in central Waikiki, the Waikiki Banyan offers one bedroom condos minutes from the ocean
                           
                          Honolulu1 BR1 BA6Ocean view Studio Sleeps 6 - FREE use of surfboards
                           
                          Honolulu1 BR1 BA9Ocean View - Sleeps 9 - FREE Surfing
                           
                          Honolulu1 BR1 BA4Waikiki studio - Ocean View
                           
                          Honolulu1 BR1 BA4FREE use of surfboard with condo!
                           
                          Honolulu1 BR2 BA6Celebrity Resorts Waikiki
                           
                          Honolulu1 BR1 BA1 Bedroom · 1 Bath· Oceanfront · Fully Furnished - Colony Surf #1502
                           
                          Honolulu2 BR2 BA4Tommy Bahama Suite on the 19th floor, Overlooks Beautiful Ala Moana
                           
                          Honolulu2 BR2 BA4Best of the Best in Waikiki - Five-Star Luxury Condominium
                           
                          Honolulu2 BR2 BAup to 6Luxurious Two Story, Two Bedroom Penthouse with Panoramic Views
                           
                          Honolulu2 BR2 BA4Tropical Resort Living - Ocean View - Executive Home
                           
                          Honolulu2 BR2 BA4Come stay in the LAP OF LUXURY in one of the most esteemed condominiums in all of Hawaii
                           
                          Honolulu2 BR1.5 BA4Updated 2 bedroom 1.5 bath on Waikiki
                           
                          Honolulu2 BR1 BA9Waikiki Two Bedroom - FREE use of surfboards
                           
                          Honolulu2 BR2 BAHokua Heaven - One-of-a-Kind Hawaiian Oceanfront
                           
                          Honolulu2 BR2.5 BA5Spacious Penthouse Unit· 180-Degree Views - Honolulu, Oahu. Waikiki Vacation Rental
                           
                          Honolulu3 + Den BR3 BA8Large Luxury (10500-sq-ft) WATERFRONT Home in Hawaii Kai-HONOLULU
                           
                          Honolulu3 BR3 BA8-10Luxurious Beachfront Oasis - Once Owned by John Travolta - Extreme Privacy with Swimming Pool & Jacuzzi
                           
                          Honolulu3 BR2 BABeachfront Estate - 5543 Kalanianaole Hiway, Honolulu
                           
                          Honolulu3 BR2 BAMoana Pacific Luxury Condo
                           
                          Honolulu4 BR6 BA8Luxurious Beachfront Estate! Immerse Yourself In Sumptuous Solitude!
                           
                          Honolulu4 BR4 BA169 Kailuana Loop, Kailua - 4 Bedroom · 4 Bath · Close to Beach · Fully Furnished - Monthly Rental
                           
                          Honolulu5 BR3 BA12-143200-Square-Foot Beautiful Home & Pool - Portlock Road Estate - Honolulu
                           
                          Honolulu6 BR7 BA10-12Honolulu, Hawaii - Oceanfront Oasis - with Pool & Jacuzzi
                           
                          Honolulu6 BR5 BA12Kailua Beach House
                           
                          Honolulu8 BR4 BA16Honolulu, Hawaii, USA - Halemana 8BR Oceanview Vacation Rental
                           
                          Kaaawa3 BR1 BA6***** CHECK THE BEST DEAL IN TOWN *****
                           
                          Kahala2 BR2.5 BABeautiful Home with Wrap Around Porch Overlooking Pool
                           
                          Kahala2 BR2 BA4Kahala Dream Condominium
                           
                          Kahala3 BR3 BA6LUXURIOUS BLACK POINT VACATION HOME
                           
                          Kahala4 BR4.5 BA8#126 Kalani Kai
                           
                          Kahala4 BR4.5 BAKahala Coastal Estate
                           
                          Kahala4 BR4 BA4 Bedroom Luxury Estate on Prestigious Kahala Avenue
                           
                          Kahala5 BR5.5 BA105 Bedroom, 5 1/2 bath oceanfront home is full of amenities including Steam room, Sauna and Pool.
                           
                          Kahala6 BR7.5 BA12#129 Kilauea Hale
                           
                          Kahala6 BR6 BAIncredible Kahala Beachfront Luxury Vacation Home
                           
                          Kahala6 BR6.5 BA12+6 Bedroom Kahala Avenue Luxury Vacation Home
                           
                          Kahuku1 BR2 BA4Serene Setting - Stroll to Restaurants & Resort!
                           
                          Kahuku2 BR2 BA2-6Affordable Family Lodging at Fabulous Turtle Bay!
                           
                          Kahuku3 BR2 BA10Bottom Level. Steps to Pool and Beach. New in 2007. Turtle Bay Resort
                           
                          Kailua1 BR1 BA2-3Come and Experience the "House of Sweet Dreams" Kailua Beach
                           
                          Kailua1 BR1 BA2"Savannah's Cabana," Wireless Internet -1 Block to Kailua Beach!
                           
                          Kailua1 BR1 BAKailua Beach Garden Rental
                           
                          Kailua2 BR2 BA6#249 Naupaka Hale
                           
                          Kailua2 BR2 BA6Beautiful 2-Bedroom Vacation Rental in Hawaii
                           
                          Kailua3 BR3 BAKailua Beach Front. Classic Hawaiian Style Home
                           
                          Kailua3 BR2 BA8Executive Home - 3 Minute Walk to Kailua Beach. Heated Pool!
                           
                          Kailua3 BR2 BA8Your Island Home Away from Home
                           
                          Kailua3 BR3 BA8Beautiful 3 bedroom, 3 bathroom home oceanfront in Kailua. Hear the sound of the waves crashing against the shore.
                           
                          Kailua3 BR2.5 BA63 Bedroom Terrace with Hot Tub near Kailua Beach
                           
                          Kailua3 BR2 BA8Hale O Ka Lani - Kailua, Hawaii
                           
                          Kailua3 BR2 BAPerfect Blend of Fun and Relaxation - Kailua Beachside
                           
                          Kailua3 BR BAWelcome to Honu Kai - Kailua, Hawaii
                           
                          Kailua3.5 BR4 BA10#262 Hale Yu Hai
                           
                          Kailua4 BR4 BA8+New Home. 3 Minute Walk to Kailua Beach. Heated Pool. Gated Community,
                           
                          Kailua4 BR3 BA4 Bedroom Executive Home. 3 Minute Walk to Kailua Beach. Pool & Spa.
                           
                          Kailua4 BR4.5 BA12Kailua Beachfront Home with Pool and Spa.
                           
                          Kailua4 BR3.5 BALuxurious Kailua Beachfront Estate with Pool & Jacuzzi
                           
                          Kailua4 BR3 BA8Kakela Kai is a newly remodled, nicely furnished, 4 bedroom, 3 bath, beachfront home!
                           
                          Kailua4 + nurser BR5.5 BA14 + cribPlace in Paradise Directly on Kailua Beach
                           
                          Kailua4 BR4 BALuxury in Paradise - Bedroom · 4 Baths · Kailua
                           
                          Kailua4 BR3 BABeachside Hawaiian Retreat - 4 Bedroom · 3 Baths · Kailua Beachside · Fully Furnished
                           
                          Kailua5 BR4 BA12Kailua Beach Estate - Pikake Hale
                           
                          Kailua5 BR4.5 BA105 Bedroom Villa with Pool - Spectacular Ocean Views!
                           
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                             Featured Property Managers  

                          www.WeddingsReunionsHawaii.com
                          "Welcome to Paradise"
                          We offer the finest accommodations for you to enjoy your Hawaiian Wedding or Reunion

                          HAWAII VACATION RENTALS
                          The Perfect Company for your next Hawaiian Islands Vacation. Resorts, Homes, Condos, Cottages, Suites, and Travel Accommodations. Luxury Travel Packages and Car Rentals.

                          www.HawaiianRentalVacations.com
                          If you are looking for place to truly relax and let go ...
                          Hawaii Rental Vacations is very excited to offer you the newest concept in Vacation Rental Accommodations, tailored to your family lifestyle and business needs ...


                          Hawaii Beach Homes
                          Relax and listen to the sound of the waves in one of our beautiful beachfront homes. Located on both the North and South shores of Oahu

                          HawaiiVacationHVC.com
                          Fabulous hotels and condos in Honolulu along Waikiki Beach from the luxury to moderate range, including some North Shore rentals from the luxury to moderate range.


                          www.TrinityProperties.com
                          With over 80 properties on two islands, Trinity has a vacation rental home that is just right for you!

                          www.HawaiianLuxuryDestinations.com
                          Enjoy Some of the Most Beautiful Homes on the Hawaii Islands of Kauai and Oahu.

                          OhanaBeachRentalsHawaii.com
                          " Oahu's # 1 Luxury Vacation Rental Resource. Specializing in Luxury Condos, Homes, and Estates on the North and South Shores"


                             Premium Listings  

                          Real Hawaii on over 6 gated acres - Ka'a'wa, between Turtle Bay & Kailua-Also Fantastic for Weddings & Reunions
                          Windward, Villa, 3-10 bedrooms, sleeps 6-21, 2-7 bathrooms. Weekly rates from 6000 to 10000 USD



                          Spa Oceanfront Private Home - 3 Lg OceanFront Decks - Wonderful Views! Private: you're the only occupants!  starting $225/night
                          North Shore, House (single), 2 bedrooms, sleeps 6, 1 bathrooms.



                          5-Acre - Beachside - Hideaway VILLA - Mokuleia
                          Mokuleia, House (single), 6 bedrooms, sleeps 18, 4.5 bathrooms. Weekly rates from 6000 to 9500 USD



                          Spectacular North Shore Beach House
                          Haleiwa, Beach House, 3 bedrooms, sleeps 8, 2 bathrooms.



                          North Shore Beachfront Vacation Home
                          North Shore, House (single), 5 bedrooms, sleeps 18, 3.5 bathrooms.