Fleming Key Vacations from $635

Name: Southernmost Beach Resort and Guesthouses
Price range: $319 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.

MirabileCondoDwntown MIA Brickell w PRKG

Downtown Miami

$635

per person

Jul 23 - Jul 26

found 8 hours ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

2/10 (2 reviews)

3BR Pool House Sleeps 8

Driftwood

$983

per person

Jul 14 - Jul 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

No reviews

The W - Bayshore Unit 1003

East Fort Lauderdale

$679

per person

Jul 17 - Jul 21

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

6/10 (2 reviews)

Casablanca Miami Beach

North Beach

$2,146

per person

Jul 12 - Jul 16

found 1 day ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

5.8/10 (323 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

Family Pool Home by Hollywood Beach

Hollywood Hills

Save 100% on your flight

$874

per person

Jun 25 - Jun 29

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

No reviews

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Fleming Key Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$203 nightly

$228 total

Jun 11 - Jun 12

Total with taxes and fees

8.4/10 Very Good! (2,219 reviews)

Everything was nice, we enjoyed our stay!

Reviewed on May 10, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$222 nightly

$250 total

Jun 8 - Jun 9

Total with taxes and fees

8.8/10 Excellent! (1,812 reviews)

Staff was very helpful with all our needs. I would only recommend that the hot tub had hot water. It was cold and the jets were weak. Otherwise it was a perfect spot for us. We will be back.

Reviewed on May 7, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

$283 nightly

$319 total

May 25 - May 26

Total with taxes and fees

8.8/10 Excellent! (3,298 reviews)

Walkable, clean, nice beach area.

Reviewed on May 10, 2026

See all 2,751 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.