Search Cottages in Fleming Key

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

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

Browse Select Fleming Key Cottages

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

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!
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
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
Miscellaneous

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
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
Bahamian Reed by Avantstay Walk to Everything! w/ Community Pool Week Long Stays Only
Front of property

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
Breezy Bungalow by Avantstay Close 2 Zachary Taylor State Park & Beach w/ Shared Pool Week Long Stays
55-inch TV with cable channels

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
Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays
Interior

Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays

3.0 star property
Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays
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!
House (3 Bedrooms) | Interior

Cozy Key West Beach Cottage: Walk to Beaches!

3.0 star property
Cozy Key West Beach Cottage: Walk to Beaches!
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
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
La Casita by Avantstay Steps to Duval Street in Key West! Month Long Stays Only
Interior

La Casita by Avantstay Steps to Duval Street in Key West! Month Long Stays Only

3.0 star property
La Casita by Avantstay Steps to Duval Street in Key West! Month Long Stays Only
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Fleming Key with Expedia?
Expedia has some superb cottages in Fleming Key, so start packing for a memorable stay on nature's doorstep. If you have a budget, choose how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a kitchen or a pool. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Fleming Key?
With Expedia's convenient filter tool, getting your hands on cheap cottages in Fleming Key couldn't be simpler. To find properties that'll make your bank balance smile, narrow down your search by star rating, budget and amenities.