Fleming Key Vacations from $525

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The Latest Fleming Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel
Avi Lux Stay
The Retreat Collection at 1 Hotel & Homes South Beach
72 Park Miami Beach Boutique Residences by IliosRentals
Viscay Hotel
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Fleming Key Hotel Deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$285 nightly
The price is $321 total per night from Nov 18 to Nov 19
$321 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (1,813 reviews)
"Amazing. Loved it and I will be back"

Reviewed on Nov 2, 2026

Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$200 nightly
The price is $225 total per night from Nov 19 to Nov 20
$225 total
Nov 19 - Nov 20
Total with taxes and fees
9/10 Wonderful! (1,893 reviews)
"I wish we didn’t have a room Right beside the road and have to wake up The employees loud cleaning with machines by the window both days at 8 am. The food should be a lot better, but it wasn’t. Service was kind and helpful."

Reviewed on Nov 3, 2026

Havana Cabana at Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $201 total per night from Dec 3 to Dec 4
$201 total
Dec 3 - Dec 4
Total with taxes and fees
Blue Flamingo Resort Key West
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.

Find the Best Fleming Key Vacation Packages

Fleming Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Miami Intl. Airport (MIA)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.