Fleming Key Vacations from $393

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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

$393

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (263 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

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,231

per person

Nov 8 - Nov 14

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

$779

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,004 reviews)

I liked having a balcony but there was no view

Reviewed on Sep 24, 2026

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$873

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,004 reviews)

President Hotel

South Beach

Save 100% on your flight

$836

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,788 reviews)

No me gustó q no tenga lugar para snacks

Reviewed on Sep 25, 2026

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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.