Fleming Key Vacations from $501

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The Latest Fleming Key vacation packages

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

President Hotel

South Beach

Save 100% on your flight

$501

per person

Jan 16 - Jan 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,874 reviews)

Staff was amazing, hotel was close to a lot of places, staff kept everything clean and fresh, bathrooms could use a little updating. Sadly I slept in everyday so I didn’t eat Breakfast. First drinks are free, bartenders was amazing.

Reviewed on Oct 25, 2026

Avi Lux Stay

East Fort Lauderdale

$751

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.6/10 Good! (10 reviews)

If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

Hotel Riu Plaza Miami Beach

Mid Beach

$725

per person

Jan 16 - Jan 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,531

per person

Dec 7 - Dec 11

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

Broadway Suites Downtown by RocketStay

Coral Way

Save 100% on your flight

$808

per person

Jan 3 - Jan 10

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (229 reviews)

Muy bien ubicado, limpio, buena relación precio calidad

Reviewed on Aug 9, 2026

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Fleming Key Hotel Deals

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$255 nightly

$287 total

Oct 28 - Oct 29

Total with taxes and fees

8.8/10 Excellent! (1,808 reviews)

"Great property."

Reviewed on Oct 24, 2026

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$219 nightly

$246 total

Nov 15 - Nov 16

Total with taxes and fees

9/10 Wonderful! (1,894 reviews)

"Receiving free breakfast everyday… Food was very good"

Reviewed on Oct 25, 2026

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$166 nightly

$187 total

Oct 27 - Oct 28

Total with taxes and fees

8.6/10 Excellent! (2,753 reviews)

"The resort was great! Two pools and so many yard games -like any yard game you can imagine. The food was pretty good, although"

Reviewed on Oct 25, 2026

See all 2,733 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.