Sugarloaf Key Cottages

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 cottages

A floating houseboat with a covered deck and seating area, docked at a marina.

1. Old Wooden Bridge Resort and Marina

Punta Brisa

Daisybel

includes taxes & fees

1 Oct - 2 Oct

A cozy outdoor patio area with a wooden deck, a white table, and a cushioned seating area.

2. OSPREY STUDIO @ The Colony-Sleeps up to 4

Old Town Key West

Debra S.

A building with a white exterior, a brick pathway, and lush greenery including palm trees and flowering plants.

3. Get your ISLAND STLYE on!

Old Town Key West

Mary S.

includes taxes & fees

1 Oct - 2 Oct

A two-story building with balconies, surrounded by lush greenery and palm trees.

4. The Dancing Rooster: 2 Blocks from Duval in Old Town.

Old Town Key West

Jonnye W.

A small, single-story building with a white exterior and a metal roof, surrounded by lush greenery and a paved patio area.

5. Find your zen at HIDDEN TREASURE

Old Town Key West

Richard M.

includes taxes & fees

7 Oct - 8 Oct

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Top Sugarloaf Key Hotel Reviews

Parrot Key Hotel & Villas

10/10 Excellent

"This property is nicer than anything we found closer to Duval Street. This property is 5 stars! Roomy, worth every penny. I loved my king size bed. I loved the properties gardens and the pools. It was quiet, private, and luxurious. I have one critique, valet parking is not needed. $30 for Valet is not needed."

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"The property offered striking beauty and an ideal location. The staff we spoke with throughout our stay were consistently friendly and welcoming. I appreciated the amenities. The complimentary continental breakfast and two welcome drinks were excellent. I would gladly return for another visit."

Find out more about Sugarloaf Key