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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Windley Key Vacations from $441

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The Latest Windley Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • On the beach, sun loungers, beach towels
    Oct 6 - Oct 10

    Pelican Hotel + Flight

    South Beach
    4 nights
    4.0 star property
    9.2/10 - Wonderful (490 reviews)
    "Love the vibe!Our recent stay at this hotel was wonderful! From the time we arrived at the hotel, we were greeted with the most warm and helpful staff! The front desk personnel Wardell was very accommodating and welcoming! We arrived very early from the airport and asked him if we could leave our bags until the check in time, and he was very kind enough to check if any room was available to accommodate us! He let us check in earlier than expected and we were able to rest and relax in our room..."
    Reviewed July 27, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    Save 100% on your flight
    $757
    $441
    per traveler
    found 1 day ago
    Pelican Hotel
  • Family Studio, 2 Double Beds, Non Smoking, Partial Sea View | View from room
    Oct 13 - Oct 16

    Casablanca Miami Beach + Flight

    North Beach
    3 nights
    3.0 star property
    5.8/10 - (327 reviews)
    "Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No..."
    Reviewed July 23, 2026
    Roundtrip • New York (EWR) - Miami (MIA)
    EWR - FLL • Nonstop FLL - EWR • Nonstop
    $7,117
    $2,797
    per traveler
    found 1 day ago
    Casablanca Miami Beach
  • 3 outdoor pools
    Sep 29 - Oct 4

    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 - MIA • Nonstop MIA - BOS • 1 stop
    $19,786
    $10,113
    per traveler
    found 1 day ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • Terrace/patio
    Sep 21 - Sep 26

    Private Apartment at the Congress + Flight

    South Beach
    5 nights
    4.0 star property
    6.0/10 - (13 reviews)
    "Loved the location its part of the Palace which I did not know... the room was not as pictured the bed was not comfortable also the elevator was not working properly had to walk up a few times or it wouldn't go to the floor it was supposed to there is absolutely no parking only valet and it was $52 but everything else was great"
    Reviewed July 28, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    Save 100% on your flight
    $797
    $459
    per traveler
    found 1 day ago
    Private Apartment at the Congress
  • Studio | In-room safe, desk, iron/ironing board, cribs (free)
    Oct 15 - Oct 18

    Viscay Hotel + Flight

    South Beach
    3 nights
    2.5 star property
    8.2/10 - Very Good (341 reviews)
    "Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand"
    Reviewed July 16, 2026
    Roundtrip • Philadelphia (PHL) - Miami (MIA)
    PHL - MIA • Nonstop MIA - PHL • Nonstop
    Save 100% on your flight
    $1,747
    $1,008
    per traveler
    found 1 day ago
    Viscay Hotel

Windley Key Hotel Deals

Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Drop Anchor

Drop Anchor
3.0 star property
0.4 mi from Windley Key
8.8 out of 10, Excellent, (1,013 reviews)
"This is the worse booking I’ve ever made via Expedia. Room had active water damage and smelled of mold. Left the property 4 hours after checking in. No staff on duty after 6:00 PM. Came back the following day walked the room with the front desk person and showed her all of the issues I found. Requested a full refund for Expedia to tell me after a week that they couldn’t get in touch with a hotel they market and profit from. I lost a lot of money and my 25th wedding anniversary was ruined."
$148 nightly
The price is $162
Aug 3 - Aug 4
Total with taxes and fees
Drop Anchor
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 Windley Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.