Fleming Key Vacations from $344

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The Latest Fleming Key vacation packages

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

Barcelona Studios Guesthouse

South Beach

Save 100% on your flight

$344

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (267 reviews)

Great but no tv in the room

Reviewed on Sep 30, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,551

per person

Nov 12 - Nov 17

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$589

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,008 reviews)

The Penguin Hotel

South Beach

Save 100% on your flight

$515

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Miami Vacation Rentals - Brickell

Brickell

Save 100% on your flight

$1,068

per person

Dec 6 - Dec 12

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (570 reviews)

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Fleming Key Hotel Deals

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$265 nightly

$298 total

Oct 6 - Oct 7

Total with taxes and fees

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$168 nightly

$189 total

Oct 6 - Oct 7

Total with taxes and fees

8.6/10 Excellent! (2,713 reviews)

"Great rooms and property. But the elevators need work. slow and only one wroking."

Reviewed on Oct 5, 2026

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$185 nightly

$208 total

Oct 6 - Oct 7

Total with taxes and fees

8.6/10 Excellent! (2,585 reviews)

"Very clean and modern room. A very quiet place as well."

Reviewed on Oct 4, 2026

See all 2,698 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.