Fleming Key Vacations from $377

Name: Oceans Edge Key West Resort, Hotel & Marina
Price range: $325 total
Rating: 8.8

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The Latest Fleming Key vacation packages

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

Creekside Inn

$377

per person

Feb 24 - Feb 27

found 6 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Staff good Room with problems: toilet, safe vault, tv, no closet, no chair, too small

Reviewed on Jan 6, 2026

The Shelborne By Proper, a Member of Design Hotels

South Beach

$875

per person

Feb 10 - Feb 13

found 5 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (56 reviews)

Excellent amenities and great location

Reviewed on Dec 31, 2025

Hawks Cay Resort

$895

per person

Feb 19 - Feb 24

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Overall a great stay. Very nice and clean condo with its own small pool. The property is beautiful and we enjoyed the tennis and pickleball facilities. Only areas for improvement were the initial delay in room being available from housekeeping and need for more service staff around the pool area.

Reviewed on Jan 4, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$5,481

per person

Feb 10 - Feb 13

found 5 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Bay Breeze Premium Apartments By Eskape Collection

Save 100% on your flight

$425

per person

Mar 10 - Mar 14

found 6 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (189 reviews)

Our two bedroom apartment was very comfortable and quiet. We enjoyed our stay very much.

Reviewed on Dec 30, 2025

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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

$298 nightly

$336 total

Jan 19 - Jan 20

Total with taxes and fees

8.6/10 Excellent! (1,871 reviews)

Very awesome and accommodating place!

Reviewed on Jan 5, 2026

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$292 nightly

$329 total

Jan 11 - Jan 12

Total with taxes and fees

8/10 Very Good! (1,831 reviews)

Room was clean. Amenities were great.

Reviewed on Jan 6, 2026

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Fully refundableReserve now, pay when you stay

$289 nightly

$325 total

Jan 8 - Jan 9

Total with taxes and fees

8.8/10 Excellent! (1,743 reviews)

Friendly staff

Reviewed on Jan 2, 2026

See all 2,834 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.