Top Highgate Independent in Sugarloaf Key, FL from ￥29,759

A waterfront with a pier, calm water, and houses with palm trees in the background.

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Our top choices for Sugarloaf Key Highgate Independent

A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

A beachside lounge with chairs and umbrellas, overlooking the ocean.

A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.

A beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, and a clear blue sky.

1. Southernmost Beach Resort and Guesthouses

Old Town Key West

Deaenna

￥25,149

￥39,796 total

includes taxes & fees

Sep 29 - Sep 30

A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

A couple holding hands in a tropical setting with palm trees and greenery.

2. Blue Flamingo Resort Key West

New Town

Esteban

￥18,586

￥29,759 total

includes taxes & fees

Sep 27 - Sep 28

A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

A marina with various boats docked, including a green and white boat named 'Jolly Roger'.

A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

A covered outdoor area with a pool, palm trees, and lounge chairs.

3. The Marker Key West Harbor Resort

Key West Historic District

Joelle

￥29,742

￥43,371 total

includes taxes & fees

Sep 30 - Oct 1

A white picket fence, a sign for Duval Gardens Bed & Breakfast, and a palm tree.

A porch with wicker chairs and a table, white railings, and a window with a view of a palm tree.

4. Duval Gardens at Southernmost Beach Resort – Adults Only

Old Town Key West

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Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

8/10 Good

"Access to Duval st."

Pier House Resort & Spa

10/10 Excellent

"The resort was well maintained, the staff very friendly, the beach, pool and restaurant made for an amazing vacation."

Blue Flamingo Resort Key West

8/10 Good

"Wish there were more options as far as eating, the staff was helpful in some ways, I think they were training a lot of them which is fine, I get it. Room was very clean. Would have been nice if there was an indoor eating area not just the outdoor bar areas but it was fine. Never were able to locate the other sister options to eat but that was ok. Food was very tasty. Beds were comfortable and pillows were firm and soft, great options, mini fridge and coffee w/water in the room, oh and the ear plugs were so cute!!!"

Beachside Resort & Residences

10/10 Excellent

"We loved this resort. Room mix up at first. Was moved to beautiful suite with walk in shower. Handicap was needed. Restaurant awesome. Tapas breakfast. Great happy hour with piano bar. Pool a d private beach. 👍 all the way. Thanks for a wonderful vacation."