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Featured Cottages in Fleming Key and around

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (120)
"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

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

9.2 out of 10, Wonderful, (12)
"Great location. Walkable to everywhere we wanted to go. Comfortable beds"
The price is €280
includes taxes & fees
29 Apr - 30 Apr
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

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

10.0 out of 10, Exceptional, (118)
"3 relaxing days"
The price is €687
includes taxes & fees
12 May - 13 May
The Dancing Rooster: 2 Blocks from Duval in Old Town.

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

9.6 out of 10, Exceptional, (11)
"Was perfect tucked away spot on quiet end of Island but walking distance to everything. "
The price is €316
includes taxes & fees
5 May - 6 May
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

HIDDEN OASIS 3 blocks from Duval

2.5 star property
9.4 out of 10, Exceptional, (86)
"Great location, loved the pool and outdoor patio"
The price is €717
includes taxes & fees
8 May - 9 May
HIDDEN OASIS 3 blocks from Duval

Get your ISLAND STLYE on!

2.0 star property
9.6 out of 10, Exceptional, (79)
"My husband enjoyed the pool and locale"
The price is €754
includes taxes & fees
24 May - 25 May
Get your ISLAND STLYE on!

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

9.8 out of 10, Exceptional, (9)
"Awesome little hideout! You feel like the only one on the island when you step in this quaint cottage! Great place to stay! "
The price is €279
includes taxes & fees
27 Apr - 28 Apr
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (155)
"Wonderful three day trip. Property was great & would stay there again."
Conch Republic Consul General's Cottage.-Historic District

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.

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

10.0 out of 10, Exceptional, (1)
"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

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

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

10.0 out of 10, Exceptional, (11)
"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: The property is close to the Southern most point. It's safe too. Property manager Rick is very helpful."
The price is €315
includes taxes & fees
4 May - 5 May
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.8 out of 10, Exceptional, (12)
"Loved how clean and quiet it was :)"
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

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

10.0 out of 10, Exceptional, (9)
"My wife and I stay at many places and I personally travel extensively for business. I've stayed in all sorts of accommodations and the most important aspect of my travel is the customer support and caliber of the people hosting my stay. I have to say, Rick is amazing, ready to accommodate and help in every way. Polite, professional and a pleasure to talk to. We highly recommend and are already planning a family trip for Easter. Thanks so much..."
The price is €280
includes taxes & fees
28 Apr - 29 Apr
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW

9.4 out of 10, Exceptional, (9)
"Wonderful, Very Clean and GreaT :) 3 "
A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW

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

9.6 out of 10, Exceptional, (13)
"Everything was great. A little noisy from across the street, but hey it's Key West :) "
The price is €316
includes taxes & fees
5 May - 6 May
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!

10.0 out of 10, Exceptional, (3)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Blue Bird was a wonderful location just off Whitehead St. Close to Southernmost area, Bahama Village resturants and Duval Loop bus stop. Very clean and well equipt kitchen, nice backyard, friendly neighbors. Parking spot in front of house was...
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!

~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

10.0 out of 10, Exceptional, (216)
"Loved the location, loved the property - it worked great for our group of 6 visiting Key West!"
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

Old Town Key West Cottage 3bed/2bath

10.0 out of 10, Exceptional, (1)
"We had an incredible stay in this house! We were very comfortable and constantly in contact with the host, who was always very communicative and helpful when we needed something. The location is perfect, just meters from the main street of Key West. The house was in perfect conditions and it’s just like the pictures! I 100% recommende it ☺️"
Old Town Key West Cottage 3bed/2bath

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
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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Other property types in Fleming Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (131)
"Would definitely stay here again! "
The price is €254
includes taxes & fees
27 Apr - 28 Apr
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (293)
"This was an amazing property. Wish we had stayed for more than a night and we're already planning a trip to Key West again just to stay here another time. Very friendly and helpful reception staff. Parking deck is directly across the street. Beautiful pool. Near the water (cruise port), a 5 minute walk to Duval Street, and the Truman Little White House was basically next door. Genuinely cannot say enough good things about this hotel."
The price is €350
includes taxes & fees
4 May - 5 May
Hyatt Vacation Club at Sunset Harbor, Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (808)
"Very tropical, on the water. Everything u need in amenities. Pools were great!"
Coconut Mallory Resort And Marina By Kees Vacations
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.