Fleming Key Vacations from $393

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The Latest Fleming Key vacation packages

Price found within the past 48 hours. Click for updated prices.

Barcelona Studios Guesthouse

South Beach

$393

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (258 reviews)

This property was absolutely amazing! Not only do they have communal toiletries (sun screen, umbrella, etc.) but they also have beach chairs for you to use, beach towels, and the staff was simply amazing! I can’t wait to return!

Reviewed on Sep 21, 2026

Cavalier Hotel South Beach

South Beach

$526

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,005 reviews)

Love it

Reviewed on Sep 21, 2026

Pelican Hotel

South Beach

$851

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (506 reviews)

Front Desk Staff was GREAT! We ate outside one night and the FOOD was DEEEE-LISH-US!!!! The only two dislikes were the bed was extremely hard. Was not comfortable...and...being on Ocean Dr, the music played until about 1am(ish). All we heard was the Bass. So if you are an early "bedder", you may not want to stsy as any hotel on Ocean Drive. But overall, the Pelican was nice! (PS: the food was really good!!)

Reviewed on Sep 21, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,160

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 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 on Jun 22, 2016

President Hotel

South Beach

Save 100% on your flight

$562

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,738 reviews)

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Fleming Key Hotel Deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$225 nightly

$253 total

Sep 29 - Sep 30

Total with taxes and fees

8.6/10 Excellent! (3,607 reviews)

"Todo estaba perfecto menos la playa estaba extremadamente sucia"

Reviewed on Sep 22, 2026

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$168 nightly

$189 total

Sep 23 - Sep 24

Total with taxes and fees

8.6/10 Excellent! (2,681 reviews)

"Was a great place beds could use a little upgrade"

Reviewed on Sep 20, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$234 nightly

$263 total

Oct 6 - Oct 7

Total with taxes and fees

8.8/10 Excellent! (1,795 reviews)

"Dont forget the addition 54.00 a night fee after you already pay 1600 something for 4 nights"

Reviewed on Sep 21, 2026

See all 2,683 properties in Fleming Key

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.