Fleming Key Vacations from $500
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The Latest Fleming Key vacation packages
Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel
South Beach
Save 100% on your flight
Price was $895, price is now $500 per person
$500
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,893 reviews)
Great location, easy to use the facilities at the President Hotel. We had an issue with some water leakage in our room which they dealt with right away and provided free breakfast the next morning.
Reviewed on Jul 13, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $11,837, price is now $5,850 per person
$5,850
per person
Sep 11 - Sep 14
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
Hotel Riu Plaza Miami Beach
Mid Beach
Save 100% on your flight
Price was $1,063, price is now $628 per person
$628
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,151 reviews)
la pisina estaba sucia los cuartos limpios pero la pisina un asco tuvimos 2 dias sin playa x el zargazo mas la pisina sucia horrible
Reviewed on Jul 12, 2026
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Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $250 total per night from Jul 16 to Jul 17
$250 total
Jul 16 - Jul 17
Total with taxes and fees
8.6/10 Excellent! (2,347 reviews)
"Great location, great service and very clean."
Reviewed on Jul 14, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $245 total per night from Aug 11 to Aug 12
$245 total
Aug 11 - Aug 12
Total with taxes and fees
8.8/10 Excellent! (3,457 reviews)
"Everything was great with our stay except that we couldn’t go on the beach due to the seaweed issue"
Reviewed on Jul 13, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
$184 nightly
The price is $207 total per night from Aug 9 to Aug 10
$207 total
Aug 9 - Aug 10
Total with taxes and fees
8.4/10 Very Good! (2,531 reviews)
"The room was super clean that was great! AC was super cold and that was huge, definitely need cold AC. There are a lot of amenities, which is great. Though the restaurant/bar closes too early, 10pm seems way too early for a hotel/resort in Key West. Also, would have been nice breakfast was more easily ..."
Reviewed on Jul 14, 2026
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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- Bahama Village Vacations
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- Custom House Museum
- All inclusive Vacation Packages Key West
- Key West Firehouse Museum
- Saint Mary Star of the Sea
- Robbie's
- Schooner Western Union
- Key West Cemetery
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- Jackson Square
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- Sails To Rails Museum at Flagler Station
- Red Barn Theater
- Key West Shipwreck Museum
- Key West Lighthouse and Keeper's Quarters Museum
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- Smathers Beach
- The Kite House
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- Clarence S. Higgs Memorial Beach Park
- Harry S. Truman Little White House
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
