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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 June
In two months
27 June - 29 June

Featured Cottages in Fleming Key

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, (121)
"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!
Terrace/patio

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 AU$594
includes taxes & fees
5 May - 6 May
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
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, (118)
"3 relaxing days"
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Terrace/patio

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 AU$594
includes taxes & fees
5 May - 6 May
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
HIDDEN OASIS 3 blocks from Duval
TV

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 AU$1,259
includes taxes & fees
8 May - 9 May
HIDDEN OASIS 3 blocks from Duval
Get your ISLAND STLYE on!
Exterior

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 AU$1,325
includes taxes & fees
24 May - 25 May
Get your ISLAND STLYE on!
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, (13)
"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 AU$604
includes taxes & fees
11 May - 12 May
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Conch Republic Consul General's Cottage.-Historic District
Pool

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (156)
"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.
Exterior detail

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
Pool

~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)
Exterior

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!
Terrace/patio

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

10.0 out of 10, Exceptional, (12)
"In town for a destination wedding, the location of this VRBO was perfect! Close to the Reach and Duval Street was an easy walk. 10 minutes to the airport and we parked our golf cart right out front. "
The price is AU$595
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)
Exterior

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)
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (218)
"Everything walking distance!!"
The price is AU$789
includes taxes & fees
16 May - 17 May
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Terrace/patio

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

9.8 out of 10, Exceptional, (10)
"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 AU$594
includes taxes & fees
5 May - 6 May
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW
Pool

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!
Terrace/patio

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 AU$596
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!
Fridge, microwave, oven, stovetop

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!
A heated pool

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

10.0 out of 10, Exceptional, (216)
"The property was located steps from all the action of Duval Street but also had the feel of a relaxing oasis."
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Old Town Key West Cottage 3bed/2bath
Fridge, microwave, oven, stovetop

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
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
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (134)
"Would definitely stay here again! "
The price is AU$513
includes taxes & fees
5 May - 6 May
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Outdoor pool

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (295)
"We had a nice stay. The property was in a great location."
The price is AU$535
includes taxes & fees
5 May - 6 May
Hyatt Vacation Club at Sunset Harbor, Key West
Coconut Mallory Resort And Marina By Kees Vacations
2 outdoor pools

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.