
Fleming Key Vacations from $285
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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 $602, price is now $285 per person
$285
per person
Mar 1 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
From the very efficient and effective check in, courteous customer service, and spotless room, our stay was great from the beginning. The place was spacious and modern. There was a big wrap around balcony (we had the two bedroom), and large kitchen. Even a washer and dryer. The only cons were the water pressure in the bathroom sink, and after a certain time, you cannot get more towels. House cleaning is "ask if you want", its not every day. For us we liked our privacy, so this worked for us. Another thing we loved was the quiet. The views were ok. Go ahead and book, you will not regret.
Reviewed on Dec 8, 2025



Hawks Cay Resort
Price was $1,372, price is now $622 per person
$622
per person
Feb 2 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,003 reviews)
Overall the resort was great! The only criticism I can add is that the villa showed some wear and tear.
Reviewed on Dec 30, 2025

Cavalier Hotel South Beach
South Beach
Price was $1,207, price is now $575 per person
$575
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Perfect location and great bonus with beach towels and two free chairs on the beach.
Reviewed on Dec 27, 2025
Fleming Key Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$311 nightly
The price is $350 total per night from Jan 7 to Jan 8
$350 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
8.6/10 Excellent! (1,835 reviews)
Pool and hot tub were very nice,chicken walk was excellent! Great staff!!!!
Reviewed on Dec 26, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$283 nightly
The price is $318 total per night from Jan 7 to Jan 8
$318 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
8/10 Very Good! (1,803 reviews)
The room was very clean and comfortable. The $15.00 for parking your car was a little of the top tho! You should really give discounts for Florida Residence too, we drove 350 miles to come see Key West and to have to pay all the fees & parking fee is a bit much!
Reviewed on Dec 26, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $328 total per night from Jan 21 to Jan 22
$328 total
Jan 21 - Jan 22, 2026
Total with taxes and fees
8.8/10 Excellent! (1,763 reviews)
So many activities and amazing staff and service. The shuttle was very convenient. I would stay here again! Perfect for families. I felt safe. Very laid back environment.
Reviewed on Dec 26, 2025
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.



















