Fleming Key Vacations from $379

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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

$379

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (258 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,839

per person

Nov 19 - Nov 22

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

$692

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

I love the room. I would definitely stay again. The only thing I would say is the showers are definitely not hot enough for me. I don’t know if I just like it too hot but that’s the only issue I really had.

Reviewed on Sep 7, 2026

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$501

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,005 reviews)

Estuvo muy bueno. Lo malo es que te enganchan las sillas pero sin las sombrillas y ahí esta el truco. De resto todo muy

Reviewed on Sep 13, 2026

President Hotel

South Beach

Save 100% on your flight

$714

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

The stay was good but we decided to take the Miami Double Deck Bus and it was awful. Rip off totally do not recommend at all. The rooms are clean and the staff was cordial and so attentive and helpful.

Reviewed on Sep 15, 2026

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Fleming Key Hotel Deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$239 nightly

$269 total

Sep 28 - Sep 29

Total with taxes and fees

8.6/10 Excellent! (3,604 reviews)

"Booked this place for the location and how many pools they had. Didn’t know until we got there that the largest pool was under renovation and completely out of service. Not the end of the world but this made the other 2 pools (combined they were the size of the 1 that was closed) more cramped. Then ..."

Reviewed on Sep 15, 2026

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$160 nightly

$180 total

Sep 17 - Sep 18

Total with taxes and fees

8.6/10 Excellent! (2,672 reviews)

"Clean room, clean pool. staff very helpful,"

Reviewed on Sep 15, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$234 nightly

$263 total

Sep 30 - Oct 1

Total with taxes and fees

See all 2,703 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.