Fleming Key Vacations from $674

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The Latest Fleming Key vacation packages

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

Hotel Victor

South Beach

Save 100% on your flight

$674

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,001 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,910

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 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 on Jun 22, 2016

President Hotel Villa

South Beach

Save 100% on your flight

$852

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,000 reviews)

The room was very clean and big. We enjoy using the rooftop pool. Breakfast is excellent. I wish they had more space in the hall to put more tables, since eating outside was too hot.

Reviewed on Oct 11, 2026

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$1,118

per person

Dec 2 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

The Penguin Hotel

South Beach

Save 100% on your flight

$747

per person

Dec 4 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,996 reviews)

Clean and comfortable

Reviewed on Oct 10, 2026

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Fleming Key Hotel Deals

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$265 nightly

$298 total

Oct 12 - Oct 13

Total with taxes and fees

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$175 nightly

$197 total

Oct 12 - Oct 13

Total with taxes and fees

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$187 nightly

$210 total

Oct 14 - Oct 15

Total with taxes and fees

9/10 Wonderful! (1,877 reviews)

"The room we booked was damaged due to significant rain in the week before however the property made it right and management was so accommodating. Free breakfast was a full hot breakfast and we ordered from a menu. The pool area was super nice and there were extra perks like smoothies jello shots ..."

Reviewed on Oct 11, 2026

See all 2,725 properties in Fleming Key

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.