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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Fleming Key

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 NZ$572
includes taxes & fees
19 Aug - 20 Aug
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
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, (19)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is NZ$572
includes taxes & fees
18 Aug - 19 Aug
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Experience the serene atmosphere of this compact building surrounded by lush tropical plants and a peaceful patio area.

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

9.6 out of 10, Exceptional, (17)
"The location was perfect, close enough to walk to anything we needed to get to. The hosts went above and beyond to be helpful and even picked us up from the airport! The room was great and felt very private."
The price is NZ$569
includes taxes & fees
10 Aug - 11 Aug
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from 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, (23)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
The price is NZ$572
includes taxes & fees
19 Aug - 20 Aug
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
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!

9.8 out of 10, Exceptional, (20)
"Will stay here again "
The price is NZ$574
includes taxes & fees
17 Aug - 18 Aug
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Stunning two-story building with a spacious balcony and lush tropical surroundings.

**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…
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.
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
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Enjoy a serene outdoor space surrounded by lush plants and a charming seating area.

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 NZ$572
includes taxes & fees
19 Aug - 20 Aug
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
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 NZ$859
includes taxes & fees
14 Aug - 15 Aug
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
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 NZ$870
includes taxes & fees
27 Aug - 28 Aug
The Dancing Rooster: 2 Blocks from Duval in Old Town.
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
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
House (2 Bedrooms) | Interior

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!
~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.
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!
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, (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
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)
"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
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!
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

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Property was great in every way."
Dena 3-night trip
Posted 12 hours ago
Pier House Resort & Spa