Fleming Key Vacations from $510

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The Latest Fleming Key vacation packages

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

Solara Surfside

Save 100% on your flight

$510

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (67 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,254

per person

Dec 3 - 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

President Hotel

South Beach

Save 100% on your flight

$624

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Rooms just didnt look like the pictures

Reviewed on Sep 30, 2026

Miami Vacation Rentals - Brickell

Brickell

Save 100% on your flight

$854

per person

Nov 12 - Nov 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (570 reviews)

Miami Vacation Rentals Downtown with Pool

Downtown Miami

Save 100% on your flight

$1,414

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

No 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

Oct 4 - Oct 5

Total with taxes and fees

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$261 nightly

$294 total

Oct 8 - Oct 9

Total with taxes and fees

8.6/10 Excellent! (3,640 reviews)

"We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view."

Reviewed on Oct 1, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$265 nightly

$298 total

Oct 4 - Oct 5

Total with taxes and fees

8.8/10 Excellent! (1,782 reviews)

"My overall experience was good. I wasn’t overly impressed, but was content. I don’t have many complaints besides the food. We ate twice at the resort and had issues both times. We decided to eat elsewhere after that."

Reviewed on Sep 30, 2026

See all 2,684 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.