Key West, Florida

Florida Vacation Rentals

A playground for all ages, Florida's world-famous beaches, championship golf courses, spectacular watersports and epic theme parks beckon. Whether you're looking for urban luxury or a quiet retreat, Florida vacation rentals offer the perfect setting for an idyllic vacation.
  • Naples Our 5-Star

    Experience refined luxury at this beachfront hotel and golf resort where spacious accommodations, a full service spa, and multiple dining options create a memorable stay.

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  • Captiva Our 4-Star

    This resort was originally a key lime plantation 100 years ago, this hotel offers spacious guest rooms, suites, and villas to make yourself feel at home amid a 330-acre wildlife preserve.

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  • Sanibel Our 3-Star

    This soothing retreat offers the ease and comfort of home, with a tranquil beachfront location.

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  • Ft. Myers Beach, Florida Our 4-Star

    Situated on a sugar-white beach overlooking the Gulf of Mexico, this resort is the ideal choice for guests seeking adventure, relaxation and fun.

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  • Ft Myers, Florida Our 4-Star

    Renew in relaxed elegance at this waterfront hotel in Cape Coral where condo-style rooms and suites offer Florida waterfront views from private balconies and fully equipped kitchens.

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  • Bonita Springs, Florida Our 4-Star

    This eco-friendly resort is set on 26 acres overlooking breathtaking Estero Bay Aquatic Preserve.

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  • Clearwater Beach Our 4-Star

    Just steps from the Gulf and Pier 60, this hotel offers the comforts of home in 287 over-sized rooms including 256 suites with amenities such as full kitchens, walk out balconies, and sleeper sofas.

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  • Miami Beach, Florida Our 5-Star

    Named among the Top 5 Hotels in Miami Beach by the 2021 Travel + Leisure World’s Best Awards, Nobu Hotel at Eden Roc Miami Beach delivers the unique chemistry and perfect balance of luxury and lifestyle.

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  • Ft. Myers Beach, Florida Our 3.5-St

    Located on a gleaming stretch of white sand, this resort promises upscale pleasures in a breathtaking setting.

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  • Universal Studios, Orlando Our 3.5-St

    Exclusive Theme Park Benefits. Relax and play in a setting inspired by classic Florida beach resorts from the 1950s and 60s, then unwind in vibrant, retro-styled rooms and suites.

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