Fleming Key Vacations from $607
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The Latest Fleming Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Avi Lux Stay
Dec 10 - Dec 13Avi Lux Stay + Flight
East Fort Lauderdale3 nights4.5 star property7.6/10 - 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 August 28, 2025Roundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop FLL - BOS • Nonstop - The Retreat Collection at 1 Hotel & Homes South Beach
Jan 28 - Feb 2The Retreat Collection at 1 Hotel & Homes South Beach + Flight
South Beach5 nights5.0 star property8.0/10 - 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 June 22, 2016Roundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop MIA - BOS • Nonstop$21,554$10,094found 1 day agoper traveler - 501 First Studio Balcony by Palermo Home
Jan 16 - Jan 21501 First Studio Balcony by Palermo Home + Flight
Downtown Miami5 nights2.0 star propertyRoundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop FLL - BOS • Nonstop$1,603$792found 1 day agoper traveler - Miami Vacation Rentals - Downtown
Jan 28 - Feb 3Miami Vacation Rentals - Downtown + Flight
Downtown Miami6 nights5.0 star property9.0/10 - Wonderful (124 reviews)"Price with fees get a bit over the average, and the garage is extremely expensive and annoying."Reviewed November 6, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop MIA - BOS • Nonstop$2,625$1,364found 1 day agoper traveler - The Club - Pool - Gym - Parking - Heart of Brickell
Jan 16 - Jan 21The Club - Pool - Gym - Parking - Heart of Brickell + Flight
Brickell5 nights4.0 star propertyRoundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop FLL - BOS • Nonstop$1,753$912found 1 day agoper traveler
Fleming Key Hotel Deals
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West4.0 star property
Stock Island, 3.7 mi from Fleming Key
9.4 out of 10, Exceptional, (1,314 reviews)
9.4/10
Exceptional
(1,314 reviews)
"Beautiful property with great food!"
$137 nightly
The price is $155
$155 total
Dec 7 - Dec 8
Total with taxes and fees
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Fairfield by Marriott Inn & Suites Key West at The Keys Collection3.5 star property
New Town, 2.9 mi from Fleming Key
8.6 out of 10, Excellent, (1,186 reviews)
8.6/10
Excellent
(1,186 reviews)
$152 nightly
The price is $171
$171 total
Nov 15 - Nov 16
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West4.0 star property
3.2 mi from Fleming Key
8.4 out of 10, Very good, (1,132 reviews)
8.4/10
Very good
(1,132 reviews)
"Everything clean and politely"
$153 nightly
The price is $172
$172 total
Nov 15 - Nov 16
Total with taxes and fees
9.0 out of 10, Wonderful, (1,570 reviews)
9.0/10
Wonderful
(1,570 reviews)
"The shuttle to town is a plus ( don’t have look for parking) Be aware some pick up times can be premium. The continental breakfast was very good and organized. The staff very helpful and friendly."
$188 nightly
The price is $212
$212 total
Nov 30 - Dec 1
Total with taxes and fees
Hilton Key West Resort & Marina
Hilton Key West Resort & Marina4.0 star property
Stock Island, 4.4 mi from Fleming Key
9.0 out of 10, Wonderful, (1,795 reviews)
9.0/10
Wonderful
(1,795 reviews)
"Fire alarm went off at 3 AM on Novembe 5th, but the siren could not be heard at all inside room 2306 due to the front vestibule. I only realized what was happening when I looked out the window and saw a crowd outside. There was absolutely zero communication or direction from hotel staff and no fire department at all on site . After 40 minutes, the alarm finally stopped, and everyone just went back inside without any directions or updates. Major safety concern. Also, when i booked the room for 2...
$170 nightly
The price is $191
$191 total
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection3.5 star property
New Town, 2.8 mi from Fleming Key
8.2 out of 10, Very good, (1,355 reviews)
8.2/10
Very good
(1,355 reviews)
"Clean room"
$140 nightly
The price is $158
$158 total
Nov 15 - Nov 16
Total with taxes and fees
8.2 out of 10, Very good, (1,000 reviews)
8.2/10
Very good
(1,000 reviews)
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
$99 nightly
The price is $111
$111 total
Nov 30 - Dec 1
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton4.0 star property
Casa Marina, 2.3 mi from Fleming Key
8.4 out of 10, Very good, (1,009 reviews)
8.4/10
Very good
(1,009 reviews)
$284 nightly
The price is $320
$320 total
Nov 8 - Nov 9
Total with taxes and fees
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.
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.
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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.