Fleming Key Vacations from $531

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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

$531

per person

Oct 25 - Nov 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (258 reviews)

This property was absolutely amazing! Not only do they have communal toiletries (sun screen, umbrella, etc.) but they also have beach chairs for you to use, beach towels, and the staff was simply amazing! I can’t wait to return!

Reviewed on Sep 21, 2026

Cavalier Hotel South Beach

South Beach

$724

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,005 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,231

per person

Nov 8 - Nov 14

found 20 hours 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

South Beach

Save 100% on your flight

$779

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,738 reviews)

Everything was great the bathroom is small other than that I had a great stay. Very friendly and helpful staff

Reviewed on Sep 24, 2026

EAST Miami

Brickell

$836

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (4,095 reviews)

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Fleming Key Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$168 nightly

$189 total

Sep 27 - Sep 28

Total with taxes and fees

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$229 nightly

$258 total

Sep 28 - Sep 29

Total with taxes and fees

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$265 nightly

$298 total

Sep 27 - Sep 28

Total with taxes and fees

8.8/10 Excellent! (1,798 reviews)

"The room was fantastic, the staff excellent , the frozen drinks weak. We had lots of fun at the pool feeding the iguanas…would definitely recommend"

Reviewed on Sep 23, 2026

See all 2,683 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.