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

Search Sugarloaf Key Cottage Rentals from CA $339

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Sugarloaf Key cottages

Exterior

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, (362 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
United States
Kathy
The price is CA $126
CA $339 total
includes taxes & fees
Sep 1 - Sep 2
Old Wooden Bridge Resort and Marina
Outdoor dining

2. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (102 reviews)
"The bedrooms and bathrooms were a little small but everything else was fantastic. We loved the outdoor spaces."
United States
Carla R.
The price is CA $399
CA $746 total
includes taxes & fees
Aug 11 - Aug 12
Canal front, dockage, 2 bedroom, 2 bath
Property grounds

3. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (32 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
The price is CA $327
CA $663 total
includes taxes & fees
Aug 11 - Aug 12
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Interior

4. Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (7 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is CA $354
CA $795 total
includes taxes & fees
Aug 12 - Aug 13
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Exterior

5. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (33 reviews)
"Jolly Rooster cottage was a prefect and great location. Cottage was very clean. We had a great girls trip!We will definitely be back."
United States
Phyllis B.
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

6. 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, (150 reviews)
"Such a great stay. A nice walk to duval for nightlife!"
United States
Mercedes A.
The Dancing Rooster: 2 Blocks from Duval in Old Town.
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Loved this place. Friendly staff. Great views. Amenities were awesome! Highly recommend!"
Dean 5-night trip
Posted 2 hours ago
Southernmost Beach Resort and Guesthouses

Find out more about Sugarloaf Key

Sugarloaf Key Cottages information

Number of reviews
529
Accommodation
104 Cottages
Lowest Price
CA $339
Highest Price
CA $795

Frequently asked questions

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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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