Fleming Key Vacations from $547

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The Latest Fleming Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A bed with white linens and a blue pillow, flanked by two bedside lamps, set against a backdrop of a clear blue sea and palm trees.
    Jan 16 - Jan 21

    The Penguin Hotel + Flight

    South Beach
    5 nights
    3.5 star property
    8.4/10 - Very good (2,049 reviews)
    "On arrival we received a free cocktail, at the President Hotel. The bar tender was very nice and accommodating. No tea only coffee available on site had to go to the President if we wanted a tea. Not laudably available. The rooms were very clean. Overall it was ok."
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $1,062
    $547
    per traveler
    found 2 days ago
    The Penguin Hotel
  • A poolside area with lounge chairs, a table with a beverage, and a view of the ocean.
    Jan 28 - Feb 2

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    5 nights
    5.0 star property
    8.0/10 - Very good (1 review)
    "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...."
    Reviewed June 22, 2016
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop MIA - BOS • Nonstop
    $21,554
    $10,094
    per traveler
    found 1 day ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • A restaurant with multiple dining areas, including a bar and a seating area with a high ceiling and exposed brick walls.
    Jan 16 - Jan 21

    The Marlin Hotel + Flight

    South Beach
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,003 reviews)
    "Despite the age of the building, this was a beautiful hotel. I loved the dark, beautifully lit hallways but bright and beachy rooms. All of the staff was friendly and very helpful. We asked for additional toiletries and they were brought up in less than 10 minutes. It’s a great location to the beach and the other art deco hotels. We would definitely stay here again."
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $1,140
    $554
    per traveler
    found 2 days ago
    The Marlin Hotel
  • A modern living room with a large window, a flat-screen TV, a potted plant, a candle, and a view of a city skyline.
    Jan 16 - Jan 21

    501 First Studio Balcony by Palermo Home + Flight

    Downtown Miami
    5 nights
    2.0 star property
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $1,603
    $792
    per traveler
    found 1 day ago
    501 First Studio Balcony by Palermo Home
  • A modern hotel room with a sofa, a small table with a telephone, a desk with a lamp, a bed with patterned bedding, a TV on the wall, and a large window with a city view.
    Dec 10 - Dec 13

    Avi Lux Stay + Flight

    East Fort Lauderdale
    3 nights
    4.5 star property
    7.6/10 - Good (10 reviews)
    "If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE. "
    Reviewed August 28, 2025
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    Save 100% on your flight
    $1,188
    $607
    per traveler
    found 1 day ago
    Avi Lux Stay

Fleming Key Hotel Deals

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
4.0 star property
Stock Island, 3.7 mi from Fleming Key
9.4 out of 10, Exceptional, (1,314 reviews)
"Beautiful property with great food!"
$137 nightly
The price is $155
Dec 7 - Dec 8
Total with taxes and fees
The Perry Hotel & Marina Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Fleming Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.