Fleming Key Vacations from $728
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The Latest Fleming Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Avi Lux Stay
Jan 21 - Jan 25Avi Lux Stay + Flight
East Fort Lauderdale4 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 • 1 stop$1,470$728found 1 day agoper traveler - The Retreat Collection at 1 Hotel & Homes South Beach
Jan 3 - Jan 7The Retreat Collection at 1 Hotel & Homes South Beach + Flight
South Beach4 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 FLL - BOS • Nonstop$31,509$14,848found 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 - MIA • Nonstop FLL - BOS • Nonstop$1,494$757found 1 day agoper traveler - E11EVEN Lifestyle - Pool, Nightlife & Downtown
Jan 15 - Jan 21E11EVEN Lifestyle - Pool, Nightlife & Downtown + Flight
Downtown Miami6 nights4.0 star property10/10 - Exceptional (1 review)"Loved this stay! The place was PERFECT. Could not ask for more!! Will definitely staying here again next time I’m in Miami."Reviewed October 20, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop FLL - BOS • Nonstop$2,655$1,348found 14 hours agoper traveler - Viscay Hotel
Jan 12 - Jan 17Viscay Hotel + Flight
South Beach5 nights2.5 star property8.2/10 - Very good (351 reviews)"Great stay"Reviewed November 4, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop FLL - BOS • Nonstop
Fleming Key Hotel Deals
Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key West5.0 star property
Old Town Key West, 1.6 mi from Fleming Key
9.2 out of 10, Wonderful, (1,220 reviews)
9.2/10
Wonderful
(1,220 reviews)
$294 nightly
The price is $331
$331 total
Nov 29 - Nov 30
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, (1,199 reviews)
8.6/10
Excellent
(1,199 reviews)
"We plan to use this hotel again! At first we thought we were disadvantaged as it is not adjacent to downtown Key West as other hotels are. We later realized that was an advantage because it was close to where we chartered a boat on our trip. It is also close and an easy walk to Stock Island where you can rent paddleboards and kayaks. Plus there are better biking options over there. These are activities we want to enjoy in addition to going to downtown KW. We used Uber, a local shuttle and a...
$159 nightly
The price is $179
$179 total
Nov 29 - Nov 30
Total with taxes and fees
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and Spa4.0 star property
Historic Seaport, 1.4 mi from Fleming Key
9.2 out of 10, Wonderful, (1,004 reviews)
9.2/10
Wonderful
(1,004 reviews)
$320 nightly
The price is $360
$360 total
Dec 1 - Dec 2
Total with taxes and fees
9.0 out of 10, Wonderful, (1,580 reviews)
9.0/10
Wonderful
(1,580 reviews)
"There was a horrible smell outside due to the hotel being next to a swampy area. My family asked for the fire place turned on and they said they were coming but no one ever showed up. As we were approaching to check in, a very drunk person tried multiple times to get my in vehicle. he had no idea that we weren’t part of his group. lol Next time I be staying in “Old Town” that part of Key West would’ve been fun to spend more time in"
$169 nightly
The price is $190
$190 total
Nov 16 - Nov 17
Total with taxes and fees
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront3.0 star property
Northside Resort, 1.9 mi from Fleming Key
8.8 out of 10, Excellent, (1,007 reviews)
8.8/10
Excellent
(1,007 reviews)
$183 nightly
The price is $206
$206 total
Nov 29 - Nov 30
Total with taxes and fees
Silver Palms Inn & Historic Homes
Silver Palms Inn & Historic Homes3.5 star property
Old Town Key West, 1.8 mi from Fleming Key
9.4 out of 10, Exceptional, (1,039 reviews)
9.4/10
Exceptional
(1,039 reviews)
"Very central location"
$229 nightly
The price is $258
$258 total
Dec 1 - Dec 2
Total with taxes and fees
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, (1,315 reviews)
9.4/10
Exceptional
(1,315 reviews)
$167 nightly
The price is $188
$188 total
Nov 30 - Dec 1
Total with taxes and fees
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton4.0 star property
Uptown - Upper Duval, 2.3 mi from Fleming Key
8.6 out of 10, Excellent, (1,069 reviews)
8.6/10
Excellent
(1,069 reviews)
"We enjoyed our stay at the Reach and it was nice to be at the beach and within walking distance of the town. Breakfast package was good value both at the Reach and sister hotel. We felt for the cost a few more amenities would be welcome particularly a shuttle to the town. The cost of parking was also extremely high"
$263 nightly
The price is $296
$296 total
Nov 30 - Dec 1
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.