Florida Keys Paddle Boarding
Florida Keys Scuba Divers
Couple in hammock, Florida Keys
Swimming with Dolphins, Florida Keys

The Florida Keys & Key West – Come As You Are

 
Discover the Florida Keys, a unforgettable destination with endless beauty, southern flair and historical charm.
  • Duck Key, 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.

    Located between Miami and Key West on picturesque Duck Key, this resort offers the perfect union of solitude and convenience. It offers well-appointed guest rooms and suites creating a laid-back tropical setting.

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  • Key West 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.

    Nestled along the south edge of the island, this landmark resort overlooks more than a 1,100-foot stretch of the largest private beach in Key West, exclusively reserved for hotel guests.

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  • Key West 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.

    Located near Smathers Beach in Key West, this hotel takes contemporary coastal design to the next level with charming guest rooms and suites that pay homage to the island's raw, natural beauty and rebellious maritime history.

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  • Key West 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.

    Set on the island's only natural-sand beach, this intimate boutique-style resort in Key West offers gorgeous ocean views and plenty of outdoor activities.

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  • Key West, 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.

    Located in historic Old Town Key West, adjacent to Mallory Square, this resort and spa blends chic style with history and cultural significance.

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  • Key West 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 offers incomparable luxury and is just minutes away from Old Town Key West.

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  • Key Largo 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.

    Renew your mind, body and soul at this magnificent beach resort rising from the wild landscapes of Key Largo.

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  • Key West 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 upscale resort is close to Key West's most popular attractions including museums, the beach, marinas, golf courses and much more.

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  • Key Largo 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.

    Offering a prime location that’s just the right amount of being-away-from-it-all, this beach resort offers unparalleled views of Florida Bay.

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  • Key West 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 all-new Hilton hotel sits at the entrance of Key West and is just minutes away from Duval Street and Mallory Square.

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  • Key West 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.

    Discover the sun-drenched island charm, enviable Old Town location, and rich history that makes this property the ideal Key West hotel.

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  • Islamorada 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.

    Located on tropical Islamorada in the Florida Keys, Amara Cay Resort is for the social. It is hip but not hipster, always welcoming and guaranteed to create lasting memories.

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  • Marathon, 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.

    Enjoy island living and serenity at the waterfront Courtyard Faro Blanco Resort.

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  • Key Largo Our 2.5-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This resort is a lush tropical paradise perfect for enjoying sunsets and visiting the best attractions the Florida Keys have to offer.

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  • Key West, 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.

    Four blocks from Duval Street, this playful oasis boasts three pools, an outdoor bar and enchantment at every turn.

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  • Key Largo 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.

    An oasis of comfort and convenience await you at this Key Largo hotel.

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  • Key Largo 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 property invites you to soak up the tropics and experience all of the endless activities the Florida Keys has to offer. With a heated pool, restaurants and bars, and fitness center on property, the fun never has to end.

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  • Key West, Florida 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 newly renovated hotel brings a fresh and contemporary look to guests' Key West experience and features rooms and suites overflowing with amenities.

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  • Key West, Florida 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.

    Just a stone's throw from the iconic Key West Lighthouse, this hotel combines manmade and natural beauty in the heart of Old Town

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  • Key West, Florida 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.

    An intimate retreat in the center of Old Town Key West, blending cottage charm with historic character.

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  • Marathon, Florida Our 2.5-Star classification designates those properties offering comfortable accommodations with standard amenities. Guests can expect dependable services in a clean and comfortable environment. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Enjoy fun in the sun and unforgettable experiences in the Middle Keys at the Fairfield Inn & Suites by Marriott Marathon Florida Keys.

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  • Key West 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 collection of historic conch homes is ideal for couples and explorers of land and sea.

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  • Islamorada 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.

    La Siesta Resort & Marina is a true Florida Keys hideaway on beautiful Islamorada. Its accommodations range from rooms and suites to oceanfront cottages and vacation homes.

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  • Key West, Florida 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.

    Combining buildings from the late 1800s and 1920s with modern updates and amenities focusing on upscale comfort.

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  • Key West 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 a gateway to the historic district of Key West and just steps away from the beach and downtown.

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  • Little Torch Key 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.

    Little Palm Island Resort & Spa is America’s only private island resort. It features thatched-roof bungalows inspired by British West Indies design with a careful nod to old world tradition.

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  • Waterfront 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 waterfront hotel in the Florida Keys is beautifully located on the Gulf of Mexico and features spacious rooms and suites with patios or balconies.

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  • Key West, Florida 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 iconic tropical mansion in Key West embodies an air of stately elegance, perfect for honeymooners and those looking for a tranquil vacation.

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