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Flight and Cheap hotel deals in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.

Blue Flamingo Resort Key West

New Town

CA $2,508

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

8.6/10 Excellent! (2,736 reviews)

They have open passes for non paying people/locals on the weekend. Couldn't get a pool chair very crowed and screaming kids running around. Bill is incorrect too. Room didn't get cleaned Not happy .

Reviewed on Nov 10, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $3,999

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Stunning, I dont have to say anymore

Reviewed on Nov 10, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $4,636

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,033 reviews)

The Perry Hotel & Marina Key West

CA $3,100

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,311 reviews)

The Gardens Hotel

Old Town Key West

CA $3,811

per person

Jan 5 - Jan 10

found 12 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Key West (EYW)

9.8/10 Exceptional! (1,006 reviews)

Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West

Reviewed on Nov 8, 2026

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3 Night Cheap holidays in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,067

per person

Jan 22 - Jan 25

found 15 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Stunning, I dont have to say anymore

Reviewed on Nov 10, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $2,204

per person

Jan 22 - Jan 25

found 15 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,033 reviews)

The Gardens Hotel

Old Town Key West

CA $2,523

per person

Jan 22 - Jan 25

found 15 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.8/10 Exceptional! (1,006 reviews)

Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West

Reviewed on Nov 8, 2026

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4 Night Cheap holidays in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.

The Palms Hotel

Old Town Key West

CA $1,513

per person

Jan 28 - Feb 1

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

9/10 Wonderful! (1,003 reviews)

We loved hanging out by the pool and having a poolside bar. The property had many lovely areas to relax and enjoy. The bike rentals were really convenient. The inn is walkable to many restaurants and shopping. The staff was very friendly. We would stay again.

Reviewed on Nov 9, 2026

The Key West Hotel

Key West Historic District

CA $4,704

per person

Jan 28 - Feb 1

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

9.2/10 Wonderful! (564 reviews)

Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!

Reviewed on Oct 29, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,241

per person

Jan 28 - Feb 1

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

8.6/10 Excellent! (3,630 reviews)

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Cheap Hotels in Lower Florida Keys

Seashell Motel

718 South Street Key West FL

12 min walk from Duval Street

Stay at this hostel in Key West. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

5 min drive from Duval Street

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. ...

Southwinds Motel

1321 Simonton Street Key West FL

11 min walk from Duval Street

Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...

See all 3,425 properties in Lower Florida Keys

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.