Oahu Vacation Rentals
Diamond Head, Oahu

Oahu Vacation Rentals

From bustling Waikiki to the dramatic waves of the North Shore, Oahu has something for everyone. Start and end your day in your island home away from home, a condo or suite vacation rental from Pleasant Holidays.

All Vacation Rentals All Hawaii Rentals

  • The Twin Fin

    The Twin Fin

    Waikiki, Oahu
    Affording stunning views of iconic Diamond Head and steps from Waikiki Beach, this lively hotel with an urban-Hawaii vibe invites guests to embrace the Aloha Spirit with daily activities, regional cuisine and live entertainment.
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    Affording stunning views of iconic Diamond Head and steps from Waikiki Beach, this lively hotel with an urban-Hawaii vibe invites guests to embrace the Aloha Spirit with daily activities, regional cuisine and live entertainment.
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  • Aulani, Disney Vacation Club Villas

    Aulani, Disney Vacation Club Villas

    Ko Olina Resort Area, Oahu
    Spacious one-, two- and three-bedroom villas with full kitchens ideal for large families that sleep up to 12 at this Hawaii beachfront resort.
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    Spacious one-, two- and three-bedroom villas with full kitchens ideal for large families that sleep up to 12 at this Hawaii beachfront resort.
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  • Embassy Suites by Hilton Waikiki Beach Walk

    Embassy Suites by Hilton Waikiki Beach Walk

    Waikiki, Oahu
    This hotel featuring one & two-bedroom suites offers spacious and comfortable accommodations just a short walk from Waikiki Beach.
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    This hotel featuring one & two-bedroom suites offers spacious and comfortable accommodations just a short walk from Waikiki Beach.
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  • Ilikai Hotel & Luxury Suites

    Ilikai Hotel & Luxury Suites

    Waikiki, Oahu
    This is a historic high-rise set above the spectacular Waikiki shoreline. One- and two-bedroom city and ocean view rooms include gourmet kitchens, lanai and Wi-Fi access.
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    This is a historic high-rise set above the spectacular Waikiki shoreline. One- and two-bedroom city and ocean view rooms include gourmet kitchens, lanai and Wi-Fi access.
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  • Ka La'i Waikiki Beach, LXR Hotels & Resorts

    Ka La'i Waikiki Beach, LXR Hotels & Resorts

    Waikiki, Oahu
    Discover the ultimate luxury getaway just steps from Waikiki Beach. Sumptuous one-, two- and three-bedroom suites with gourmet kitchens range in size from 770 to 2,200 square feet.
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    Discover the ultimate luxury getaway just steps from Waikiki Beach. Sumptuous one-, two- and three-bedroom suites with gourmet kitchens range in size from 770 to 2,200 square feet.
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  • The Ritz-Carlton Residences, Waikiki Beach

    The Ritz-Carlton Residences, Waikiki Beach

    Waikiki, Oahu
    Discover a distinctive resort experience with stylishly appointed studios, three- and four-bedroom suites offering ocean views and premium resort amenities.
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    Discover a distinctive resort experience with stylishly appointed studios, three- and four-bedroom suites offering ocean views and premium resort amenities.
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  • Aston at the Waikiki Banyan

    Aston at the Waikiki Banyan

    Waikiki, Oahu
    Just a block from the beach, this affordable, family-friendly property features 1-bedroom condos with mountain or ocean views near shopping and restaurants.
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    Just a block from the beach, this affordable, family-friendly property features 1-bedroom condos with mountain or ocean views near shopping and restaurants.
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  • Castle Waikiki Shore

    Castle Waikiki Shore

    Waikiki, Oahu
    Waikiki's only condominium resort directly on the beach features comfortably appointed studios as well as one- and two-bedroom suites.
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    Waikiki's only condominium resort directly on the beach features comfortably appointed studios as well as one- and two-bedroom suites.
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  • Espacio the Jewel of Waikiki

    Espacio the Jewel of Waikiki

    Waikiki, Oahu
    A rich suite of on-site amenities awaits at this luxury hotel for guests who seek the ultimate in personalized service and privacy.
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    A rich suite of on-site amenities awaits at this luxury hotel for guests who seek the ultimate in personalized service and privacy.
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