Fleming Key Vacations from $290

Name: Margaritaville Beach House Key West
Price range: $264 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.

Barcelona Studios Guesthouse

South Beach

Save 100% on your flight

$290

per person

Oct 24 - Oct 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (98 reviews)

Overall, it was great and easy

Reviewed on Sep 17, 2025

Henrosa Hotel

South Beach

Save 100% on your flight

$363

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (818 reviews)

Beach staff was rude.

Reviewed on Sep 8, 2025

Ridley House - Key West Historic Inns

Key West Historic District

$924

per person

Dec 7 - Dec 12

found 2 days ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (815 reviews)

The room we were in was directly attached to the kitchen area so it was very noisy starting at 6am every morning. Other than the noise in the morning the stay was fine. I would say it would be nice if the people making breakfast could have been a little quieter in the morning.

Reviewed on Sep 10, 2025

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$617

per person

Nov 25 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

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

Great staff. Nice rooms close to beach

Reviewed on Sep 2, 2025

EAST Miami Residences

Downtown Miami

Save 100% on your flight

$558

per person

Dec 14 - Dec 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (74 reviews)

Convenient for shopping and food.

Reviewed on Sep 2, 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

$199 nightly

$223 total

Sep 28 - Sep 29

Total with taxes and fees

8.8/10 Excellent! (1,720 reviews)

"Excellent Property"

Reviewed on Sep 14, 2025

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

Fully refundableReserve now, pay when you stay

$176 nightly

$198 total

Sep 21 - Sep 22

Total with taxes and fees

8.4/10 Very Good! (1,526 reviews)

"Wonderful site and sounds. The rooms were amazing."

Reviewed on Sep 14, 2025

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard, Key West, FL

Fully refundableReserve now, pay when you stay

$235 nightly

$264 total

Oct 2 - Oct 3

Total with taxes and fees

8.6/10 Excellent! (1,780 reviews)

"Conveniently located hotel. SHUTTLE to Duvall Street & Airport"

Reviewed on Sep 14, 2025

See all 2,803 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.