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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is €315
includes taxes & fees
1 Oct - 2 Oct
Old Wooden Bridge Resort and Marina
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

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.4 out of 10, Exceptional, (63 reviews)
"We had such a great time on our visit. The place was exactly like the only photos and we enjoyed the pool, the area and the other visiters. Beautiful Old Town feel!"
United States
Debra S.
OSPREY STUDIO @ The Colony-Sleeps up to 4
A building with a white exterior, a brick pathway, and lush greenery including palm trees and flowering plants.

3. Get your ISLAND STLYE on!

Get your ISLAND STLYE on!
Old Town Key West
9.6 out of 10, Exceptional, (84 reviews)
"Good location. Provided everything that was listed. The unit was very clean."
United States
Mary S.
The price is €515
includes taxes & fees
1 Oct - 2 Oct
Get your ISLAND STLYE on!
A two-story building with balconies, surrounded by lush greenery and palm trees.

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

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Town Key West
9.8 out of 10, Exceptional, (151 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
The price is €719
includes taxes & fees
20 Oct - 21 Oct
The Dancing Rooster: 2 Blocks from Duval in Old Town.
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

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Great location, clean and well equipped."
United States
Richard M.
The price is €601
includes taxes & fees
7 Oct - 8 Oct
Find your zen at HIDDEN TREASURE
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.
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Top Sugarloaf Key Hotel Reviews

Parrot Key Hotel & Villas

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."
Krystal 1-night trip
Posted 5 hours ago
Parrot Key Hotel & Villas

Find out more about Sugarloaf Key

Sugarloaf Key Cottages information

Number of reviews
608
Accommodation
99 Cottages
Lowest Price
€315
Highest Price
€719

Frequently asked questions

Why book your cottage in Sugarloaf Key with Expedia?
Expedia has some excellent cottages in Sugarloaf Key, so start planning for a memorable holiday close to nature. If you have a set budget, click on how much you want to spend and the preferred star rating of your property. Or, make your way to the filters to search for cottages with a pool or free WiFi. We'll help you find the perfect place whatever your style of travel or plans.
How can I find cheap cottages in Sugarloaf Key?
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What is there to do in Sugarloaf Key near my cottage?
After you've unpacked your things and settled in, set out and explore the wonderful things Sugarloaf Key has to offer. Florida Keys Beaches is a great attraction to add to your must-do list.

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