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Check prices for these dates

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Jul 18 - Jul 20
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Featured Cottages in Sugarloaf Key

Old Wooden Bridge Resort and Marina
Relax in a cozy seating area with a sofa and small table, and enjoy a fully equipped kitchenette with microwave, coffee maker, and refrigerator.

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (244)
"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!
Escape to a tranquil beach paradise surrounded by swaying palm trees and the soothing sound of the ocean.

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!
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Front of property

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 star property
8.0 out of 10, Very Good, (2)
"The living room furniture and mattresses are not the most comfortable. Worn. Mattresses in small bedroom need replacement. Air conditioner does not reach small bedroom. "
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only
Guests can enjoy the beach with its clear waters and sandy shore, surrounded by rocks and boulders.

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!
Relax by the pool with ocean views and lounge under shaded umbrellas.

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
Escape to a serene beach paradise with palm trees swaying gently in the breeze.

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
Enjoy cooking in this well-equipped kitchen with a stove, microwave, and dishwasher.

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
Enjoy a tranquil beach experience with access to the ocean and lush palm trees.

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
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
Front of property

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

3.0 star property
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
Interior

Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

3.0 star property
9.0 out of 10, Wonderful, (2)
"Good detailed check in info and property info. Clean. Upstairs bath had standing water while showering. Bed downstairs very uncomfortable. Pool was nice but cold. "
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Relax on the beach with stunning views of the calm sea and shade from palm trees.

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
Interior

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
Relax in a serene garden setting with a round table and wicker chairs.

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
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Interior

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3.0 star property
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Papaya Place by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Hot Tub!
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

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
Enjoy a serene coastal scene with a sailboat on the water, framed by a palm tree and rocky foreground.

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
Guests can enjoy access to the beach with turquoise waters and a sandy shore.

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!
Enjoy cooking in this fully equipped kitchen with a sink, refrigerator, and dishwasher.

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
Enjoy a tranquil beach experience with palm trees swaying in the breeze and the ocean in the background.

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
Guests can enjoy access to the beach and scenic views of the turquoise waters.

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.