Name: Southernmost Beach Resort and Guesthouses
Price range: $266 total
Rating: 8.6

The Latest Lower Sugarloaf Key vacation packages

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

per person

Oct 15 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,003 reviews)

A Perfect Stay on Ocean Drive I had a wonderful stay at this hotel right on Ocean Drive in South Beach. The location is unbeatable—just steps from the beach and in the heart of all the action. The customer service was attentive and friendly, always ready to help with a smile. The on-site restaurant was a pleasant surprise—great food, good vibes, and drinks. The decor throughout the hotel is stylish and inviting, with that classic South Beach charm. Highly recommend for anyone looking to soak up the Miami vibe in comfort and style!

Reviewed on Jul 31, 2025

Casablanca Miami Beach

North Beach

per person

Oct 8 - Oct 15

found 1 day ago

Roundtrip flight included

New York (JFK) to Miami (MIA)

5.8/10 (307 reviews)

It was great for beach access. Nothing in our room worked. Coffee pot was broke. Stove was broke. We had to switch on and off the breakers to use it. Toilet would tflush half the time.

Reviewed on Jun 21, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Oct 11 - Oct 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Henrosa Hotel

South Beach

per person

Oct 15 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (809 reviews)

friendly staff, clean rooms, 1 block away from the beach

Reviewed on Jul 22, 2025

Hotel Colonnade Coral Gables, Autograph Collection

Coral Gables Section

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,005 reviews)

I liked the property. Checking in staff was good. Check out staff not so good. Also hotel charge 25 dollar destination fee per day. As per Expedia u pay what u see on the booking. So not happy about that.

Reviewed on May 26, 2025

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Lower Sugarloaf Key Hotel Deals

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

Fully refundableReserve now, pay when you stay

$194 nightly

$218 total

Aug 12 - Aug 13

Total includes taxes and fees

8.4/10 Very Good! (1,429 reviews)

"Very relaxing. We honestly never had to rely on to many people once we got there. Everything was nice."

Reviewed on Aug 6, 2025

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard, Key West, FL

Fully refundableReserve now, pay when you stay

$164 nightly

$184 total

Sep 7 - Sep 8

Total includes taxes and fees

7.6/10 Good! (1,525 reviews)

"Just five minutes from the airport and the shuttle will take you into the Mallory Square area every hour. 10:30 is last shuttle back. Hopefully in the near future all the restaurants will be open and lobby bar but I didn’t have use any and didn’t know they weren’t done with renovations. Should have ..."

Reviewed on Aug 5, 2025

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Fully refundable

$237 nightly

$266 total

Aug 24 - Aug 25

Total includes taxes and fees

8.6/10 Excellent! (2,662 reviews)

"Great spot for my teenager. Easy parking. Very clean grounds . Would book here again"

Reviewed on Aug 6, 2025

See all 3,505 properties in Lower Sugarloaf 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.