Fleming Key Vacations from $588

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The Latest Fleming Key vacation packages

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

Casa Boutique Hotel

South Beach

Save 100% on your flight

$588

per person

Dec 16 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Clean. Classy. Conveniently located.

Reviewed on Oct 2, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,321

per person

Nov 15 - Nov 21

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

The Local House

South Beach

Save 100% on your flight

$955

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,001 reviews)

The hotel has a great atmosphere. The check in lady was very nice she explained everything on details . Beach was just a block from the hotel . Love this hotel and definitely recommend it . Restaurant is downstairs too and very convenient

Reviewed on Oct 5, 2026

1 Hotel South Beach

South Beach

Save 100% on your flight

$2,584

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,654 reviews)

All good overall.

Reviewed on Oct 8, 2026

Miami Vacation Rentals Downtown with Pool

Downtown Miami

Save 100% on your flight

$654

per person

Dec 9 - Dec 12

found 24 hours ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Miami (MIA)

No reviews

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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 11 - Oct 12

Total with taxes and fees

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$195 nightly

$219 total

Oct 11 - Oct 12

Total with taxes and fees

8.6/10 Excellent! (2,592 reviews)

"Front desk people act like you bother them"

Reviewed on Oct 8, 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.