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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Fleming Key

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

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

10.0 out of 10, Exceptional, (19)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is AU$512
includes taxes & fees
27 Aug - 28 Aug
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 AU$763
includes taxes & fees
14 Aug - 15 Aug
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Terrace/patio

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$523
includes taxes & fees
10 Aug - 11 Aug
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Conch Republic Consul General's Cottage.-Historic District
Pool

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!
1 bedroom, free WiFi, bed sheets

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 AU$519
includes taxes & fees
12 Aug - 13 Aug
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Terrace/patio

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

9.6 out of 10, Exceptional, (23)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
The price is AU$514
includes taxes & fees
3 Aug - 4 Aug
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Heart of Downtown Key West Cottage With Off-Street Parking
Exterior

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
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Exterior

**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…

10.0 out of 10, Exceptional, (139)
"great location wish we could use pool!!! lovely stay"
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Terrace/patio

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.
Outdoor dining

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.
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Terrace/patio

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

9.8 out of 10, Exceptional, (17)
"Super location on quiet end of Duval. Easy access to restaurants, pubs, beach, etc. Check-in super easy. Take advantage of the shuttle. Room is simple, but all you need for a quick trip - bed, bath, fridge. "
The price is AU$523
includes taxes & fees
4 Aug - 5 Aug
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Find your zen at HIDDEN TREASURE
Outdoor dining

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
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Beach nearby, beach towels

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

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 AU$1,076
includes taxes & fees
27 Aug - 28 Aug
The Dancing Rooster: 2 Blocks from Duval in Old Town.
~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.
~ROYAL POINCIANA COTTAGE~ Come and indulge yourself in some KW sunshine!
Terrace/patio

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

9.4 out of 10, Exceptional, (3)
"The best at the best price! "
~ROYAL POINCIANA COTTAGE~ Come and indulge yourself in some KW sunshine!
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!
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Exterior

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

10.0 out of 10, Exceptional, (7)
"Property was clean, and staff were nice and helpful. Good location too"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Pool

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

10.0 out of 10, Exceptional, (7)
"The property was in a perfect location and great for 2 couples. The public pool in the back was quite shaded but we had no issue finding sun elsewhere. The only thing in the kitchen is a mini fridge and a microwave so do not plan on cooking meals in the cottage. On the bright side, Key West is full of amazing restaurants you don’t want to miss out on. "
~Hibiscus Cottage~ Adults Only cottage near Duval with 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
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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