Fleming Key Vacations from $516

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The Latest Fleming Key vacation packages

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

Balfour Miami Beach, a Registry Collection Hotel

South Beach

Save 100% on your flight

$516

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,007 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,844

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

Villa Italia by At Mine Hospitality

South Beach

$544

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

10/10 Exceptional! (92 reviews)

Villa Italia is a great place to stay in South Beach, really close to everything, the beach, bars, restaurants, public transport but also really peaceful, the garden was a welcome area to relax in, the rooms were spacious, the bed was really comfortable and the room was nice and cool in the Miami heat, good to have a safe and fridge in the room too as well as the use of a well equipped communal kitchen area, the staff were very friendly and the hosts were very quick to respond when needed

Reviewed on Sep 17, 2026

President Hotel

South Beach

Save 100% on your flight

$678

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)

Rooftop pool is great for cool off at anytime. Very convenient base because everything is around you. The beach is 1 minute away, loads of food spots, busses are all close by if you need them and hotel staff are lovely.

Reviewed on Sep 17, 2026

The Penguin Hotel

South Beach

Save 100% on your flight

$651

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,963 reviews)

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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

$225 nightly

$253 total

Sep 28 - Sep 29

Total with taxes and fees

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$160 nightly

$180 total

Sep 20 - Sep 21

Total with taxes and fees

8.6/10 Excellent! (2,678 reviews)

"I stayed with my fiancée Labor Day weekend and we had an okay stay. Paying extra breakfast was not worth it. Some staff were great others were rude specially the servers at the breakfast bar."

Reviewed on Sep 19, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$234 nightly

$263 total

Oct 4 - Oct 5

Total with taxes and fees

8.8/10 Excellent! (1,790 reviews)

"Great little place with very cute vibes and super friendly staff."

Reviewed on Sep 18, 2026

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.