Name: Southernmost Beach Resort and Guesthouses
Price range: $411 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

Save 100% on your flight

$540

per person

May 26 - May 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (1,002 reviews)

I stay here twice a year, love it. Cheap, great location. If you’re not picky, this is not for you.

Reviewed on Apr 12, 2026

Casablanca Miami Beach

North Beach

$3,795

per person

Jun 20 - Jun 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

5.8/10 (322 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

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,418

per person

May 21 - May 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Pelican Hotel

South Beach

Save 100% on your flight

$648

per person

May 19 - May 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (443 reviews)

Amazing staff and best location.

Reviewed on Apr 7, 2026

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$891

per person

Jun 17 - Jun 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Room was clean and had ocean views. The staff was amazing! We ate a breakfast and a dinner at the hotel and both were amazing as well!

Reviewed on Apr 14, 2026

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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

$229 nightly

$258 total

May 10 - May 11

Total with taxes and fees

8.2/10 Very Good! (2,086 reviews)

Travelled with small children. The site stated there was a hot tub, but we could not find the hot tub and the pool was cold, making it hard for my family to enjoy the pool when we couldn’t warm up in a hot tub. The live music was quite loud, with the bass traveling pretty much uninterrupted into ...

Reviewed on Apr 14, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$309 nightly

$347 total

May 12 - May 13

Total with taxes and fees

8.8/10 Excellent! (1,814 reviews)

We were not guaranteed ocean view rooms even though we booked that, but still ended up with a beautiful ocean view in the top floor. We had great access to Smathers Beach! Overall, I don’t think it was worth over $8k including plane tickets to go here for a week.

Reviewed on Apr 14, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

$365 nightly

$411 total

May 12 - May 13

Total with taxes and fees

8.8/10 Excellent! (3,220 reviews)

The resort overall was amazing! Close proximity to the beach and Duval Street was so accessible. It would have been nice if the pool bars were open later in the evening. Our room was basic but clean. A full length mirror would have been great as well as a longer vanity in the bathroom. Not enough ...

Reviewed on Apr 14, 2026

See all 2,745 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.