Fleming Key Vacations from $721

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The Latest Fleming Key vacation packages

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

Avi Lux Stay

East Fort Lauderdale

$721

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.6/10 Good! (10 reviews)

If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,496

per person

Nov 29 - Dec 4

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

Lyfe Resort & Residences

Hollywood Beach

Save 100% on your flight

$769

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (37 reviews)

We stay here every time. We really like everything.

Reviewed on Oct 22, 2026

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$1,780

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$1,821

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,008 reviews)

Clean room. Neat decor and friendly staff.

Reviewed on Oct 22, 2026

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Fleming Key Hotel Deals

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$275 nightly

$310 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (1,804 reviews)

"Not enough towels for all guests. Soap pump broken. Phone not working when we tried to call front desk for previously stated issues. When arriving at front desk, not given a resolution to any of these issues. If I’m paying $500 a night for a room, I expect it to be exceptional or property at least ..."

Reviewed on Oct 23, 2026

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$236 nightly

$265 total

Oct 30 - Oct 31

Total with taxes and fees

9/10 Wonderful! (1,884 reviews)

"It's was a great place to stay at!!!"

Reviewed on Oct 22, 2026

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$166 nightly

$187 total

Oct 25 - Oct 26

Total with taxes and fees

See all 2,733 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.