Search Fleming Key Cottage Rentals from CA $134

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Check prices for these dates

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Aug 8 - Aug 10
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Aug 29 - Aug 31
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Sep 26 - Sep 28

Browse Select Fleming Key Cottages

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Enjoy a serene outdoor space surrounded by lush plants and a charming seating area.

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (16)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is CA $134
CA $456 total
includes taxes & fees
Aug 3 - Aug 4
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

10.0 out of 10, Exceptional, (1)
"Easy walk to everything! Comfortable stay. "
The price is CA $325
CA $675 total
includes taxes & fees
Aug 14 - Aug 15
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Relax in a serene oasis with a hot tub surrounded by lush tropical plants and a wooden fence.

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

10.0 out of 10, Exceptional, (18)
"Will stay here again "
The price is CA $134
CA $456 total
includes taxes & fees
Aug 3 - Aug 4
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Conch Republic Consul General's Cottage.-Historic District
Relax by the serene pool surrounded by lush greenery and a charming building.

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (161)
"Cute, charming, clean and quiet. Great location. "
Conch Republic Consul General's Cottage.-Historic District
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Comfortable bedroom with two beds, a wall-mounted TV, and a ceiling fan.

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is CA $134
CA $460 total
includes taxes & fees
Aug 12 - Aug 13
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Relax in a secluded outdoor space with a hot tub surrounded by lush tropical plants and trees.

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

9.6 out of 10, Exceptional, (22)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
The price is CA $134
CA $456 total
includes taxes & fees
Aug 3 - Aug 4
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Heart of Downtown Key West Cottage With Off-Street Parking
Cozy home with a front porch and garden, perfect for relaxation.

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Enjoy a serene atmosphere in this charming house with a covered porch and lush green surroundings.

Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking

9.2 out of 10, Wonderful, (74)
"Really nice property just as the photos had everything we needed, great surroundings with character the pool area was perfect and well kept a very relaxing and friendly environment . The attached history to the Conch Republic was very interesting and maintained. Communications with Roberta were again very easy and in a timely & friendly manner Easy walk to Duval st and other attractions. All in all a great place to stay and would highly recommend "
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
One Bedroom Cottage House in Old Town Key West by the Hemingway House.
Enjoy a seaside meal at this beachside dining setup, complete with a beautifully set table and elegant centerpiece.

One Bedroom Cottage House in Old Town Key West by the Hemingway House.

One Bedroom Cottage House in Old Town Key West by the Hemingway House.
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Relax on the beach with lounge chairs and shaded areas under umbrellas, steps from the ocean.

Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex

10.0 out of 10, Exceptional, (196)
"Had another wonderful week at Sea Breeze Cottage. Perfect home, location, amenities, and host. Love going there. "
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Find your zen at HIDDEN TREASURE
Relax on the covered patio with a wicker sofa and chairs, surrounded by lush greenery and a grill for outdoor cooking.

Find your zen at HIDDEN TREASURE

3.0 star property
9.6 out of 10, Exceptional, (9)
"The property and location is great! The private deck was awesome. "
Find your zen at HIDDEN TREASURE
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!
~ROYAL POINCIANA COTTAGE~ Come and indulge yourself in some KW sunshine!
Terrace/patio

~ROYAL POINCIANA COTTAGE~ Come and indulge yourself in some KW sunshine!

10.0 out of 10, Exceptional, (2)
"The best at the best price! "
~ROYAL POINCIANA COTTAGE~ Come and indulge yourself in some KW sunshine!
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Enjoy the serene beach scene with turquoise waters and a sandy shore, surrounded by large rocks and lush trees.

The Dancing Rooster: 2 Blocks from Duval in Old Town.

10.0 out of 10, Exceptional, (122)
"The house was perfect for our group of 3 couples- we loved sitting out on the front porch - got lucky and parked golf cart in front every evening- close to Duval St - quiet area "
The price is CA $553
CA $954 total
includes taxes & fees
Aug 27 - Aug 28
The Dancing Rooster: 2 Blocks from Duval in Old Town.
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Relax by the pool surrounded by lush greenery and modern amenities.

~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool

10.0 out of 10, Exceptional, (7)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a wonderful stay at the Hibiscus Cottage. It has obviously had a recent renovation but did not lose the look and feel of an old conch house. Comfortable furnishings and a surprisingly large master with an en-suite bath that would rival that...
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Surrounded by palm trees and a body of water, this resort offers a tranquil atmosphere and a central swimming pool.

Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

10.0 out of 10, Exceptional, (6)
"Property was clean, and staff were nice and helpful. Good location too"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.
Terrace/patio

~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.

8.0 out of 10, Very good, (1)
~MARGARITA COTTAGE~ Bask in sunshine and lounge by your pool in paradise.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
House (2 Bedrooms) | Interior

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
House (2 Bedrooms) | 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, (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
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
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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Top Fleming Key Hotel Reviews

Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

10/10 Excellent
"Good hotel and people friendly. The area is super nice "
Juan 2-night trip
Posted 11 hours ago
Fairfield Inn and Suites by Marriott Key West