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

Search Sugarloaf Key Cottage Rentals from CA $335

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (367 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
The price is CA $125
CA $335 total
includes taxes & fees
Sep 28 - Sep 29
Old Wooden Bridge Resort and Marina
Outdoor dining

2. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
8.6 out of 10, Excellent, (188 reviews)
"Very nice property, as advertised. Great location for boating and fishing. "
United States
Lawrence L.
The price is CA $229
CA $529 total
includes taxes & fees
Sep 9 - Sep 10
Canal Front home with easy Ocean access
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 $323
CA $655 total
includes taxes & fees
Sep 16 - Sep 17
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Outdoor dining

4. HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (102 reviews)
"All around amazing place! Location was perfect! "
United States
Daniel M.
The price is CA $263
CA $852 total
includes taxes & fees
Sep 30 - Oct 1
HIDDEN OASIS 3 blocks from Duval
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, (34 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.
The price is CA $445
CA $828 total
includes taxes & fees
Sep 23 - Sep 24
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

6. 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 CA $275
CA $877 total
includes taxes & fees
Sep 14 - Sep 15
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sugarloaf Key Hotel Reviews

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Nice"
Kenneth 1-night trip
Posted 1 hour ago
Hilton Garden Inn Key West / The Keys Collection

Find out more about Sugarloaf Key

Sugarloaf Key Cottages information

Number of reviews
723
Accommodation
101 Cottages
Lowest Price
CA $335
Highest Price
CA $877

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 vacay 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.

Explore a world of travel with Expedia