Florida Keys Cheap Vacations
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Flight and Cheap hotel deals in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8/10 Very Good! (1,010 reviews)
So fun. Loved my room and having Dolphin Connection right there for my kids. Food at all the restaurants from poolside to fancy was delicious.
Reviewed on Aug. 10, 2025
Pier House Resort & Spa
Key West Historic District
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,014 reviews)
The bathroom was very nice. The rest of the room was just ok. The common hallway had trash on the floor for the entire weekend. Nobody swept the floor at all. For the money you pay there are better hotels.
Reviewed on Aug. 18, 2025
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View all trips5* Cheap holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
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View all trips3 Night Cheap holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8/10 Very Good! (1,010 reviews)
So fun. Loved my room and having Dolphin Connection right there for my kids. Food at all the restaurants from poolside to fancy was delicious.
Reviewed on Aug. 10, 2025
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See all available trips from Columbus to Florida Keys
View all trips4 Night Cheap holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort
Northside Resort
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.2/10 Very Good! (2,009 reviews)
I thought the location was perfect, the pool was very nice. The room unfortunately, almost none of the plugs worked to charge our phones which made it very challenging. Aside from that it was everything it said it was going to be.
Reviewed on Aug. 18, 2025
Pier House Resort & Spa
Key West Historic District
per person
Nov 10 - Nov 14
found 13 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Key West (EYW)
9/10 Wonderful! (1,014 reviews)
The bathroom was very nice. The rest of the room was just ok. The common hallway had trash on the floor for the entire weekend. Nobody swept the floor at all. For the money you pay there are better hotels.
Reviewed on Aug. 18, 2025
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View all tripsCheap Hotels in Florida Keys
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (1,495 reviews)
"Overall it was a great resort that offered activities and a free continental breakfast. Omelette station was a pleasant surprise."
Reviewed on Aug. 15, 2025
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd, Key West, FL
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
8/10 Very Good! (1,997 reviews)
"The entry door not too secure when you leave the room."
Reviewed on Aug. 16, 2025
Southwinds Motel
1321 Simonton Street, Key West, FL
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,156 reviews)
"Staff was very nice and proficient. Allowed me to check in early that was much appreciated!"
Reviewed on Aug. 16, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.