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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Featured Cottages in Sugarloaf Key

Old Wooden Bridge Resort and Marina
Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (241)
"price - clean and newly renovated boats - nice staff - easy check in/out."
Old Wooden Bridge Resort and Marina
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Interior

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

3.0 star property
10.0 out of 10, Exceptional, (3)
"Our second time staying here. Great location. Everything you would need for a couple. Clean,comfortable. Will rent again if available next year."
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only
Interior

Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only

3.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I loved our stay at Linger Longer. We hadeverything we needed for a top notch vacation. Beds and couch were very comfortable. The pool was great. We were able to relax and unwind."
Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
Outdoor pool

Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

3.0 star property
10.0 out of 10, Exceptional, (5)
"First timers and would definitely come back!! "
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Interior

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

3.0 star property
9.0 out of 10, Wonderful, (4)
"Perfect location, lovely place. I got COVID so had to leave two days after arrival. Bummer!"
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Fridge, microwave, oven, stovetop

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

3.0 star property
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Amelia Home by Avantstay In Historic Old Town w/ Pool
Interior

Amelia Home by Avantstay In Historic Old Town w/ Pool

3.0 star property
10.0 out of 10, Exceptional, (2)
Amelia Home by Avantstay In Historic Old Town w/ Pool
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Beach

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3.0 star property
9.0 out of 10, Wonderful, (2)
"Easy access to Smathers Beach across the street. Great location for families with children. "
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Beach House Condo by Avantstay Communal Pool Gated Community Great Location Week Long Stays
Front of property

Beach House Condo by Avantstay Communal Pool Gated Community Great Location Week Long Stays

3.0 star property
Beach House Condo by Avantstay Communal Pool Gated Community Great Location Week Long Stays
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Outdoor dining

Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

3.0 star property
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Papaya Place by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Hot Tub!
Interior

Papaya Place by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Hot Tub!

3.0 star property
Papaya Place by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Hot Tub!
Casa Grande by Avantstay Dt Key West Near South Beach w/ Pool
Interior

Casa Grande by Avantstay Dt Key West Near South Beach w/ Pool

3.0 star property
Casa Grande by Avantstay Dt Key West Near South Beach w/ Pool
Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays
Interior

Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays

3.0 star property
Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays
Cozy Key West Beach Cottage: Walk to Beaches!
Interior

Cozy Key West Beach Cottage: Walk to Beaches!

3.0 star property
Cozy Key West Beach Cottage: Walk to Beaches!
Lavender Jungle by Avantstay Great Location w/ Patio & Shared Pool! Week Long Stays Only
Interior

Lavender Jungle by Avantstay Great Location w/ Patio & Shared Pool! Week Long Stays Only

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay. "
Lavender Jungle by Avantstay Great Location w/ Patio & Shared Pool! Week Long Stays Only
Key West Charming by Avantstay Communal Pool Gated Community Near Fort Zachary Taylor Park Week Long Stays
Interior

Key West Charming by Avantstay Communal Pool Gated Community Near Fort Zachary Taylor Park Week Long Stays

3.0 star property
Key West Charming by Avantstay Communal Pool Gated Community Near Fort Zachary Taylor Park Week Long Stays
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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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.