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Flight and Pet-friendly hotel deals in Lower Florida Keys

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

The Perry Hotel & Marina Key West

CA $1,497

per person

Jan 12 - Jan 17

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,311 reviews)

The Gardens Hotel

Old Town Key West

CA $3,342

per person

Jan 28 - Feb 1

found 19 hours ago

Roundtrip 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

The Marker Key West Harbor Resort

Key West Historic District

CA $3,110

per person

Jan 19 - Jan 24

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.2/10 Wonderful! (1,033 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,796

per person

Jan 28 - Feb 1

found 19 hours ago

Roundtrip flight included

Calgary (YYC) to Key West (EYW)

8.6/10 Excellent! (3,630 reviews)

This was a great resort away from the busyness of Duval St. and yet it wa very walkable to downtown if you wish. I wish the beach area was a bit cleaner, from the sargassum, but I dont think that was anything the resort to do. Overall it was a wonderful place to be!

Reviewed on Nov 12, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,586

per person

Jan 28 - Feb 1

found 19 hours ago

Roundtrip flight included

Calgary (YYC) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Stunning, I dont have to say anymore

Reviewed on Nov 10, 2026

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3 Night Pet-friendly 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 $2,326

per person

Jan 28 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Stunning, I dont have to say anymore

Reviewed on Nov 10, 2026

The Gardens Hotel

Old Town Key West

CA $2,790

per person

Jan 28 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,518

per person

Jan 28 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

8.6/10 Excellent! (3,630 reviews)

This was a great resort away from the busyness of Duval St. and yet it wa very walkable to downtown if you wish. I wish the beach area was a bit cleaner, from the sargassum, but I dont think that was anything the resort to do. Overall it was a wonderful place to be!

Reviewed on Nov 12, 2026

Don't see what you're looking for?

See all available trips from Columbus to Lower Florida Keys

View all trips

4 Night Pet-friendly holidays in Lower Florida Keys

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,796

per person

Jan 28 - Feb 1

found 19 hours ago

Roundtrip flight included

Calgary (YYC) to Key West (EYW)

8.6/10 Excellent! (3,630 reviews)

This was a great resort away from the busyness of Duval St. and yet it wa very walkable to downtown if you wish. I wish the beach area was a bit cleaner, from the sargassum, but I dont think that was anything the resort to do. Overall it was a wonderful place to be!

Reviewed on Nov 12, 2026

The Key West Hotel

Key West Historic District

CA $5,245

per person

Jan 28 - Feb 1

found 19 hours ago

Roundtrip flight included

Calgary (YYC) 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

The Gardens Hotel

Old Town Key West

CA $3,342

per person

Jan 28 - Feb 1

found 19 hours ago

Roundtrip 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

Don't see what you're looking for?

See all available trips from Columbus to Lower Florida Keys

View all trips

Pet-friendly Hotels in Lower Florida Keys

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

4 min drive from Duval Street

Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...

8.8/10 Excellent! (1,816 reviews)

"Really enjoyed our brief stay and we wished we planned to stay longer. Definitely want to come back. Rooms are great. Property amenities like the shuttle to and from downtown, pool, and tin cup chalice restaurant are great! Staff super friendly and helpful. Loved the text check ins from the manager ..."

Reviewed on Nov 12, 2026

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

6 min drive from Duval Street

Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...

9/10 Wonderful! (1,903 reviews)

"The shuttle service is extremely helpful if you don’t have a car given it is quietly away from the heavy tourist area. The pool was wonderful with an array of floats. Nice temperature! Bar service and breakfast were great. Staff was very nice and informative about places to go and eat. They could ..."

Reviewed on Nov 11, 2026

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

16 min walk from Duval Street

Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...

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.