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.
  • Hyatt Regency Clearwater Beach Resort and Spa
    Hyatt Regency Clearwater Beach Resort and Spa
    Clearwater Beach 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.

    Close to the Gulf of Mexico and Pier 60, this hotel offers the comforts of home in 287 oversized rooms, including 256 suites, with amenities such as full kitchens, walk-out balconies, and sleeper sofas.

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  • The Resort at Longboat Key Club
    The Resort at Longboat Key Club
    Longboat Key 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.

    Escape to a blissful oasis filled with captivating views of the Gulf at The Resort at Longboat Key Club.

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  • Residence Inn Clearwater Beach
    Residence Inn Clearwater Beach
    Clearwater Beach 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.

    Relax in home-inspired studios and suites with stunning views of Clearwater Bay, conveniently located across the street from Clearwater Beach.

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  • Waterline Villas & Marina, Autograph Collection
    Waterline Villas & Marina, Autograph Collection
    Anna Maria Island 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.

    Enjoy incredible views and relaxation at this charming oasis. Take a bike ride around the beautiful city or take a dip in the outdoor pool.

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  • The Vinoy Resort & Golf Club, Autograph Collection
    The Vinoy Resort & Golf Club, Autograph Collection
    St. Petersburg 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.

    This waterfront resort in the heart of dynamic downtown St. Petersburg captures the magic of Florida's Golden Age and the resort's rich history through a fully renovated sophisticated and stylish lens.

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  • Beach House Suites by The Don CeSar
    Beach House Suites by The Don CeSar
    St. Petersburg 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.

    Beach House Suites by The Don CeSar is where the perfect beach vacation begins. This all-suite hotel is ideal for families, groups or those looking for extended-stay comfort.

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  • Universal's Cabana Bay Beach Resort
    Universal's Cabana Bay Beach Resort
    Universal Orlando Resort 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.

    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 with exclusive theme park benefits.

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  • Sheraton Vistana Resort Villas Lake Buena Vista/Orlando
    Sheraton Vistana Resort Villas Lake Buena Vista/Orlando
    Universal Studios, Orlando 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.

    With a convenient location near Disney Springs and other famous Orlando attractions, this hotel features one- and two-bedroom villas for a relaxing family vacation.

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  • Westgate Lakes Resort & Spa
    Westgate Lakes Resort & Spa
    Orlando, Florida 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 a full-service, lakefront resort and spa near Disney World offering all the comforts of a fully furnished home with accommodations ranging from studios to spacious four-bedroom villas.

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  • Melia Orlando Celebration
    Melia Orlando Celebration
    Orlando, Florida 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.

    An oasis of stylish comfort, this all-suite hotel is just a stone's throw from Orlando’s many theme parks and attractions.

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