
Fleming Key Vacations from $540
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The Latest Fleming Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Creekside Inn
Save 100% on your flight
Price was $1,056, price is now $540 per person
$540
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (1,002 reviews)
I stay here twice a year, love it. Cheap, great location. If you’re not picky, this is not for you.
Reviewed on Apr 12, 2026

Casablanca Miami Beach
North Beach
Price was $9,627, price is now $3,795 per person
$3,795
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
5.8/10 (322 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



Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,639, price is now $891 per person
$891
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Room was clean and had ocean views. The staff was amazing! We ate a breakfast and a dinner at the hotel and both were amazing as well!
Reviewed on Apr 14, 2026
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Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $258 total per night from May 10 to May 11
$258 total
May 10 - May 11
Total with taxes and fees
8.2/10 Very Good! (2,086 reviews)
Travelled with small children. The site stated there was a hot tub, but we could not find the hot tub and the pool was cold, making it hard for my family to enjoy the pool when we couldn’t warm up in a hot tub. The live music was quite loud, with the bass traveling pretty much uninterrupted into ...
Reviewed on Apr 14, 2026

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$309 nightly
The price is $347 total per night from May 12 to May 13
$347 total
May 12 - May 13
Total with taxes and fees
8.8/10 Excellent! (1,814 reviews)
We were not guaranteed ocean view rooms even though we booked that, but still ended up with a beautiful ocean view in the top floor. We had great access to Smathers Beach! Overall, I don’t think it was worth over $8k including plane tickets to go here for a week.
Reviewed on Apr 14, 2026

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$365 nightly
The price is $411 total per night from May 12 to May 13
$411 total
May 12 - May 13
Total with taxes and fees
8.8/10 Excellent! (3,220 reviews)
The resort overall was amazing! Close proximity to the beach and Duval Street was so accessible. It would have been nice if the pool bars were open later in the evening. Our room was basic but clean. A full length mirror would have been great as well as a longer vanity in the bathroom. Not enough ...
Reviewed on Apr 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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