Fleming Key Vacations from $248

Name: Beachside Resort & Residences
Price range: $217 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.

Broadmore Miami Beach

North Beach

Save 100% on your flight

$248

per person

Jan 21 - Jan 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.6/10 (369 reviews)

Staff was very nice

Reviewed on Nov 4, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$645

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (39 reviews)

Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back !

Reviewed on Nov 1, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$11,017

per person

Jan 1 - Jan 6

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Bentley Hotel South Beach

South Beach

$1,212

per person

Jan 1 - Jan 6

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (390 reviews)

Beautifully renovated with great additional touches like Continental breakfast and champagne at 5:00

Reviewed on Nov 7, 2025

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$386

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,004 reviews)

Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.

Reviewed on Nov 4, 2025

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Fleming Key Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Fully refundableReserve now, pay when you stay

$208 nightly

$234 total

Nov 30 - Dec 1

Total with taxes and fees

8.8/10 Excellent! (1,733 reviews)

We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate.

Reviewed on Nov 2, 2025

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard, Key West, FL

Fully refundableReserve now, pay when you stay

$157 nightly

$177 total

Nov 30 - Dec 1

Total with taxes and fees

7.8/10 Good! (1,648 reviews)

Beautiful room, great view, love the pools, bars and lawn games

Reviewed on Nov 3, 2025

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

Fully refundableReserve now, pay when you stay

$193 nightly

$217 total

Nov 17 - Nov 18

Total with taxes and fees

8.6/10 Excellent! (1,655 reviews)

Staff good but never clean our room

Reviewed on Nov 3, 2025

See all 2,814 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.