
Fleming Key Vacations from $396
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The Latest Fleming Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Bay Breeze Premium Apartments By Eskape Collection
Save 100% on your flight
Price was $751, price is now $396 per person
$396
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (222 reviews)
The staff were very accommodating! The location was perfect. However, the apartment did not have basic kitchen items like dish soap, paper towels or spices, I had to DoorDash those items.
Reviewed on Jun 13, 2026

Casablanca Miami Beach
North Beach
Price was $5,491, price is now $2,130 per person
$2,130
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026



Beach Plaza
South Beach
Save 100% on your flight
Price was $1,008, price is now $548 per person
$548
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (169 reviews)
Great location, just a block from the beach and ocean drive. Easy check-in and check-out. Limited lockers to keep luggage if you arrive early and aren't able to check-in yet which was very convenient. Older building although the room itself was clean and well kept. A/c worked well. Did not have the chance to use the pool although towels were provided in the lobby. There does not appear to be staff regularly in the lobby although they do reply quickly via text (calling will prompt you to text them instead). There was security posted in the lobby during the night and we did notice a staff member by the door outside at night assisting guests to get into the lobby as after a certain time the front doors are locked and only accessible by code. Overall good value, would stay again.
Reviewed on Jun 16, 2026
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Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
$184 nightly
The price is $207 total per night from Jun 22 to Jun 23
$207 total
Jun 22 - Jun 23
Total with taxes and fees
8.4/10 Very Good! (2,421 reviews)
"Muy limpió y muy buen lugar para ir de vacaciones."
Reviewed on Jun 20, 2026

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
$286 nightly
The price is $322 total per night from Jun 22 to Jun 23
$322 total
Jun 22 - Jun 23
Total with taxes and fees
8.8/10 Excellent! (3,376 reviews)
"★★☆☆☆ 2/5 Stars Southernmost Beach Resort is located in a beautiful part of Key West, and we arrived looking forward to a relaxing beachfront getaway. Unfortunately, the experience did not live up to the premium price. First, the costs add up quickly. In addition to an already expensive nightly room ..."
Reviewed on Jun 19, 2026

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $227 total per night from Jun 21 to Jun 22
$227 total
Jun 21 - Jun 22
Total with taxes and fees
8.6/10 Excellent! (2,299 reviews)
"Nice rooms and very nice staff!"
Reviewed on Jun 19, 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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- Ernest Hemingway Home and Museum
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- Donkey Milk House
- The Kite House
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- Mallory Dock
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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.



















