Fleming Key Vacations from $542

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The Latest Fleming Key vacation packages

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

Hotel Victor

South Beach

Save 100% on your flight

$542

per person

Dec 17 - Dec 20

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,001 reviews)

Lovely stay, gave a free gift for my boyfriends 30th birthday which was very kind and appreciated. Beautiful room and probably the most comfortable bed I’ve ever slept in! Lovely hotel. Thank you for a wonderful and memorable stay!

Reviewed on Oct 11, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$13,699

per person

Dec 1 - Dec 6

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

1 Hotel South Beach

South Beach

$5,193

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,654 reviews)

The Local House

South Beach

Save 100% on your flight

$980

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

EAST Miami Residences

Brickell

Save 100% on your flight

$2,118

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (152 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 13 - Oct 14

Total with taxes and fees

8.8/10 Excellent! (1,798 reviews)

"The staff was very receptive and friendly. I did not get the room I booked, I booked 2 bedroom room with 1 king and 2 queens and got a 3 queen room with no balcony. The one bedroom had no dressers or closet. The only closet for the whole group was in the shared bathroom that was approx. 18 inches ..."

Reviewed on Oct 11, 2026

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$175 nightly

$197 total

Oct 13 - Oct 14

Total with taxes and fees

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$187 nightly

$210 total

Oct 14 - Oct 15

Total with taxes and fees

9/10 Wonderful! (1,878 reviews)

"This resort is AMAZING!!!! If you don't want to, you never have the leave the resort, as EVERYTHING IS THERE!!! The Mojito Bar is awesome, food is great!!! Bartender Lana at the Mojito Bar is THE BEST!!! THE ENTIRE STAFF IS AMAZING!!! GOING BACK, I THINK IN FEW WEEKS, AGAIN!!!!"

Reviewed on Oct 11, 2026

See all 2,725 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.