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Our top choices for Sugarloaf Key cottages

2.5 star property
8.6 out of 10, Excellent, (282)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina
8.6 out of 10, Excellent, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
The price is HK$1,750
HK$2,943 total
includes taxes & fees
19 Jan - 20 Jan 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cottage in Stock Island

Living Life Dockside
The price is HK$2,940
HK$4,438 total
includes taxes & fees
4 Jan - 5 Jan 2026
Living Life Dockside
10.0 out of 10, Exceptional, (29)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
The price is HK$2,224
HK$4,626 total
includes taxes & fees
9 Jan - 10 Jan 2026
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Cottage in Old Town Key West

OSPREY STUDIO @ The Colony-Sleeps up to 4
2.0 star property
9.6 out of 10, Exceptional, (54)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
OSPREY STUDIO @ The Colony-Sleeps up to 4
9.6 out of 10, Exceptional, (10)
"I nice place cool place to go back to after touring Key West."
United States
Karen V.
The price is HK$3,382
HK$5,755 total
includes taxes & fees
9 Jan - 10 Jan 2026
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
The price is HK$2,224
HK$4,626 total
includes taxes & fees
9 Jan - 10 Jan 2026
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
10.0 out of 10, Exceptional, (25)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is HK$2,224
HK$4,627 total
includes taxes & fees
9 Jan - 10 Jan 2026
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
9.8 out of 10, Exceptional, (26)
"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "
United States
Richele
The price is HK$2,224
HK$4,627 total
includes taxes & fees
9 Jan - 10 Jan 2026
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
9.8 out of 10, Exceptional, (23)
"Great little place, perfect for southernmost area."
United States
Lee G.
The price is HK$2,239
HK$4,622 total
includes taxes & fees
4 Jan - 5 Jan 2026
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
9.8 out of 10, Exceptional, (27)
"Great location! Fun place to stay! Responses to our questions/needs very promptly! "
United States
Teressa S.
The price is HK$2,240
HK$4,623 total
includes taxes & fees
4 Jan - 5 Jan 2026
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Cottage in Old Town Key West

HIDDEN OASIS 3 blocks from Duval
2.5 star property
9.6 out of 10, Exceptional, (96)
"We absolutely loved this place! It was quaint and quiet location. It was beautifully landscaped and I loved the Hidden Oasis unit and would stay there again!"
United States
Kathryn W.
The price is HK$4,526
HK$8,212 total
includes taxes & fees
17 Jan - 18 Jan 2026
HIDDEN OASIS 3 blocks from Duval
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

Find out more about Sugarloaf Key

Sugarloaf Key Cottages information

Number of reviews
724
Accommodation
109 Cottages
Lowest Price
HK$2,943
Highest Price
HK$8,212

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?
A great way to find cheap cottages in Sugarloaf Key is with Expedia's convenient filter tool. Narrow your search by budget, star rating and amenities to grab awesome rates in just a few clicks.
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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