Cheap Vacations in Florida Keys 2026

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Flight and Cheap hotel deals in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

CA $1,199

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

9.2/10 Wonderful! (1,360 reviews)

Balcony curtains need to be changed.

Reviewed on Aug 16, 2026

Hawks Cay Resort

CA $1,969

per person

Oct 4 - Oct 11

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.2/10 Very good! (1,009 reviews)

Parrot Key Hotel & Villas

Northside Resort

CA $2,081

per person

Oct 23 - Oct 27

found 1 hour ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

9/10 Wonderful! (1,438 reviews)

Amara Cay Resort

Matecumbe

CA $1,415

per person

Oct 4 - Oct 11

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,292 reviews)

Best place to stay !!

Reviewed on Aug 15, 2026

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

CA $1,482

per person

Oct 4 - Oct 11

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.6/10 Excellent! (1,167 reviews)

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5* Cheap holidays in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

CA $1,199

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

9.2/10 Wonderful! (1,360 reviews)

Balcony curtains need to be changed.

Reviewed on Aug 16, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

3 Night Cheap holidays in Florida Keys

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

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

CA $1,395

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Miami (MIA)

8.6/10 Excellent! (1,167 reviews)

Hawks Cay Resort

CA $1,687

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Miami (MIA)

8.2/10 Very good! (1,009 reviews)

Pier House Resort & Spa

Key West Historic District

CA $1,474

per person

Sep 30 - Oct 2

found 3 hours ago

Roundtrip flight included

Edmonton (YEG) to Key West (EYW)

9/10 Wonderful! (1,258 reviews)

No comment

Reviewed on Aug 15, 2026

Don't see what you're looking for?

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4 Night Cheap holidays in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

CA $1,199

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

9.2/10 Wonderful! (1,360 reviews)

Balcony curtains need to be changed.

Reviewed on Aug 16, 2026

Ibis Bay Beach Resort

Northside Resort

CA $1,649

per person

Oct 23 - Oct 27

found 1 hour ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

8.2/10 Very good! (2,329 reviews)

Parrot Key Hotel & Villas

Northside Resort

CA $2,081

per person

Oct 23 - Oct 27

found 1 hour ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

9/10 Wonderful! (1,438 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

Cheap Hotels in Florida Keys

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. ...

8.6/10 Excellent! (1,381 reviews)

"Love this property. Second time staying here. Quaint, nothing fancy but wonderful staff and great location."

Reviewed on Aug 14, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

3 hours drive from Duval Street

Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...

See all 8,271 properties in 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.