Fleming Key Vacations from $388

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The Latest Fleming Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Barnacle Resort
The Retreat Collection at 1 Hotel & Homes South Beach
Pelican Grand Beach Resort - A Noble House Resort
Park Central South Beach
EAST Miami
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Fleming Key Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $209 total per night from Aug 26 to Aug 27
$209 total
Aug 26 - Aug 27
Total includes taxes and fees
8.4/10 Very Good! (1,465 reviews)
"Food options was great, the bed comfort was a little to firm, but the linens was awesome, the suite was very equipped and beautifully updated. Did not get in the pool because the water was not circulating clean and maintenance at night, very nice pool area, but felt the pool water was not clean."

Reviewed on Aug 17, 2025

Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $142 total per night from Aug 27 to Aug 28
$142 total
Aug 27 - Aug 28
Total includes taxes and fees
7.8/10 Good! (1,069 reviews)
"Loved the pool and convince of hotel. Staff was Excellent!!"

Reviewed on Aug 17, 2025

Hilton Garden Inn Key West / The Keys Collection
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $264 total per night from Sep 3 to Sep 4
$264 total
Sep 3 - Sep 4
Total includes taxes and fees
8.6/10 Excellent! (1,776 reviews)
"This has been the best experience I had and I will come back my son still asking me to go back and the free cookies so good thank you for a amazing time"

Reviewed on Aug 19, 2025

Margaritaville Beach House Key West
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.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.