Fleming Key Vacations from $436

Name: Southernmost Beach Resort and Guesthouses
Price range: $285 total
Rating: 8.6

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The Latest Fleming Key vacation packages

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

Cavalier Hotel South Beach

South Beach

$436

per person

Feb 23 - Feb 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

Nice staff, great area

Reviewed on Dec 9, 2025

Creekside Inn

$667

per person

Feb 28 - Mar 5

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

Clean room. Quiet despite facing US1. Walked to dinner and our kayak adventure

Reviewed on Dec 13, 2025

Casablanca Miami Beach

North Beach

$470

per person

Feb 25 - Mar 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (311 reviews)

I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

Brickell Floor 31 Sea View-Free Parking by Palermo Home

Brickell

$649

per person

Feb 25 - Mar 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

No reviews

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,732

per person

Feb 3 - Feb 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

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Fleming Key Hotel Deals

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$226 nightly

$254 total

Dec 16 - Dec 17

Total with taxes and fees

8.6/10 Excellent! (1,780 reviews)

It was overall great but one night at 2 am the fire alarm went off for Like 25mins and no body give reasons not even a single staff member was there to provide guidance or shutdown the alarms

Reviewed on Dec 14, 2025

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$175 nightly

$197 total

Dec 16 - Dec 17

Total with taxes and fees

8/10 Very Good! (1,758 reviews)

This was really great! It was quiet, peaceful and everything about this place was just so accommodating. My family and I slept very good, we were very comfortable and the staff was very welcoming and catered to us the entire time of our stay. If we visit again, we will be back!

Reviewed on Dec 12, 2025

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

$253 nightly

$285 total

Dec 18 - Dec 19

Total with taxes and fees

8.6/10 Excellent! (2,918 reviews)

Beautiful beach property. Great pools, fun activities, lovely pier to sun bask on. Clean rooms. Avalon house all decked out for Christmas. Second time here, highly recommend!

Reviewed on Dec 11, 2025

See all 2,843 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.