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Check prices for these dates

Next weekend
18 July - 20 July
In two weeks
25 July - 27 July
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured Cottages in Fleming Key

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 AU$510
includes taxes & fees
14 July - 15 July
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

The price is AU$860
includes taxes & fees
9 Aug - 10 Aug
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 AU$510
includes taxes & fees
14 July - 15 July
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, (17)
"We enjoyed the location, hot tub and outside sitting area."
The price is AU$510
includes taxes & fees
15 July - 16 July
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, (20)
"We enjoyed the location and staff was very responsive. My preference would have been a more private space but was everything as advertised."
The price is AU$521
includes taxes & fees
13 Aug - 14 Aug
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, (131)
"Perfect spot for small group or couple to stay one block over from Duval St. Highly recommend staying here!"
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, (195)
"This condo is beautiful! We booked this condo because of the back porch table and seating. Location is within walking distance to all attractions and restaurants Looking forward to next year!"
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)
"Clean, perfect location in Old Town Key West. The property manager was so accommodating and quickly got back to me with answers to my questions. Would definitely stay there again. "
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)
"Beautiful bungalow overlooking water. The property was fun to explorer."
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, (2)
~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
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
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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