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Check prices for these dates

Next weekend
8 Aug - 10 Aug
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15 Aug - 17 Aug
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29 Aug - 31 Aug
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26 Sept - 28 Sept

Featured Cottages in Fleming Key

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!
Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only
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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, (2)
"Linger Longer is the perfect place to stay~ the home was well appointed, with lovely aesthetic and very comfortable! The pool was a big plus; the Truman Annex is in the best location ~ central to countless activities and restaurants. The office management team was quick to address questions/issues. We cannot wait to plan our next visit back…"
Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
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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!
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
Guests can enjoy access to the beach with turquoise waters and a sandy shore.

Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only

3.0 star property
10.0 out of 10, Exceptional, (1)
"There are 3 things I would say could and should be better. 1) extra toilet paper. There was only one partial roll in each bathroom and one extra partial roll. 2) no shampoo/conditioner. 3) no directions to the pool. I had to call and find out where it was. For the amount you pay, you’d think those items would be available as there are everywhere else I’ve stayed. "
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
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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!
Amelia Home by Avantstay In Historic Old Town w/ Pool
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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
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
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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!
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
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
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!
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
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Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3.0 star property
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
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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
Beach House Condo by Avantstay Communal Pool Gated Community Great Location Week Long Stays
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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
Casa Grande by Avantstay Dt Key West Near South Beach w/ Pool
Enjoy a serene beach experience with palm trees and access to the ocean.

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
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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
Breezy Bungalow by Avantstay Close 2 Zachary Taylor State Park & Beach w/ Shared Pool Week Long Stays
Relax in this inviting living room with a large TV, comfortable sofa, and a floral armchair.

Breezy Bungalow by Avantstay Close 2 Zachary Taylor State Park & Beach w/ Shared Pool Week Long Stays

3.0 star property
7.0 out of 10, Good, (2)
"Excellent location. A very cozy home. Close walk to Duval and around town. It was great that a parking spot and washer/dryer was included. The pots and pans definitely need to be updated though. There was not a decent pan with nonstick coating to use to make eggs. We were aware of a fire inspection to occur one day between 8 am and 5 pm. However, we were awoken to the fire alarm beeps at 630 am, 635 am, and 650 am. We were not happy! I know it’s Florida, but we also had a surprise...
Breezy Bungalow by Avantstay Close 2 Zachary Taylor State Park & Beach w/ Shared Pool Week Long Stays
Bahamian Reed by Avantstay Walk to Everything! w/ Community Pool Week Long Stays Only
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Bahamian Reed by Avantstay Walk to Everything! w/ Community Pool Week Long Stays Only

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful and very convenient location! Walking to everything! It had all of the supplies we needed and even some beach towels and chairs, which is a nice touch! "
Bahamian Reed by Avantstay Walk to Everything! w/ Community Pool Week Long Stays Only
Conch Adventure by Avantstay Great Location w/ Patio, Outdoor Dining and Shared Pool! Week Long Stays
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Conch Adventure by Avantstay Great Location w/ Patio, Outdoor Dining and Shared Pool! Week Long Stays

3.0 star property
8.0 out of 10, Very good, (1)
"Clean condo close to all the action. My only issue was that this is a downstairs condo and the guests upstairs sounded like giants when they walked, not their fault just the way it was built so be aware of that. Also there is no conventional oven, a toaster oven and convection. It was clean and close to everything you would need. Air conditioning worked great and outdoor area was nice for sitting. Also parking was super easy. "
Conch Adventure by Avantstay Great Location w/ Patio, Outdoor Dining and Shared Pool! 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 Fleming Key with Expedia?
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How can I find cheap cottages in Fleming Key?
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