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.
  • Ko Olina Resort Area, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Spacious 1, 2 & 3-bedroom villas with full kitchens ideal for large families that sleep up to 12 at this Hawaii beachfront resort.

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  • Ko Olina Resort Area, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Inspired by the wonders and traditions of Hawaii, Aulani has been uniquely designed for families.

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  • North Shore, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Surrounded by the beauty and majesty of O'ahu's legendary North Shore, this luxurious resort embodies the very essence of Hawaii.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This all-suite resort, just a short walk from Waikiki Beach, offers spacious and comfortable accommodations.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Recently renovated, this exclusive condominium resort offers spacious and elegantly furnished with one and two-bedroom suites with fully-equipped chef inspired kitchens, in-room washer/dryer and ocean views.

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  • Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    This world-renowned hotel is celebrated for gracious hospitality, exemplary cuisine and timeless, understated elegance.

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  • Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Just two blocks to Waikiki Beach, this relaxed family oriented condominium resort features island style living with their one- and two-bedroom accommodations with full kitchens.

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  • Ko Olina Resort Area, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    This exclusive beach resort on Oahu's sunny west coast combines thrilling adventure with authentic Hawaiian tradition.

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  • Ko Olina Resort Area, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Set within the beautiful Ko Olina resort, this secluded beachfront oasis offers luxuriously appointed guest rooms and villa accommodations.

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  • Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    Ilikai Hotel & Luxury Suites is a historic high-rise set above the spectacular Waikiki shoreline.

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  • Ko Olina Resort Area, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    No Resort Fee. Along a 2-mile stretch of Hawaii's most pristine white sand beaches, this resort blends panoramic oceans views with an opulent vacation experience.

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  • Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Discover the exceptional value of every stay at OHANA Waikiki East by Outrigger, set in the midst of the city's dynamic cultural scene, just five minutes from the beach and within walking distance of virtually every conceivable type of activity.

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  • Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Just a block from the beach, this family-friendly property provides easy access to shopping and restaurants at an affordable price.

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  • Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This contemporary boutique hotel located just a short stroll to Waikiki Beach features beautifully furnished accommodations in a desirable location on Kalakaua Avenue.

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  • Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This boutique condo brings fresh contemporary style and understated chic to the heart of Waikiki.

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  • Waikiki, Oahu Our 2-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment.

    Situated in the heart of one of the world’s most popular vacation destinations, this hotel is close to shopping, restaurants, and nightlife.

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  • Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Waikiki's only beachfront condominium, this resort features panoramic ocean views and modern conveniences.

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  • Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    This hotel is conveniently located just a block from the beach and shopping and offers a wealth of amenities.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This Waikiki hotel offers a romantic oceanfront paradise with luxurious accommodations, six swimming pools and memorable dining experiences.

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  • Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Discover the debut of a new and distinctive resort experience at The Ritz-Carlton Residences, Waikiki Beach featuring stylishly-appointed suites, incomparable ocean views and legendary service.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This hotel within the Hilton Hawaiian Village Waikiki Beach Resort offers upscale suite accommodations with balconies and full kitchens

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  • Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    This ultra-luxury all-suite resort is just steps from Waikiki Beach, vibrant entertainment and exclusive shopping.

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  • Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This stunning urban resort is a private oasis, combining great design with personal service.

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  • Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    This affordable hotel in the heart of Waikiki, just two blocks from the beach, offers commanding views of the mountains and the Pacific Ocean.

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  • Waikiki, Oahu Our 2-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment.

    This mid-rise hotel offers spacious accommodations with a host of amenities to ensure a comfortable stay.

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Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]