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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 60 Cottages in Fleming Key with updated reviews, rates, and availability.

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, (119)
"This cottage was amazing for so many different reasons. Location, quiet, and detail to guests needs. Marcela was a great communicator. No need to communicate too much, everything worked great! We are returning next year!"
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!

9.0 out of 10, Wonderful, (10)
"Great location, very helpful staff "
The price is AED 555
AED 1,371 total
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.
Exterior

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

10.0 out of 10, Exceptional, (117)
"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 price is AED 1,653
AED 2,762 total
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!
Terrace/patio

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

9.6 out of 10, Exceptional, (11)
"We really enjoyed our recent long weekend at the Seagull property! It started with an airport pickup from Wisi, who also picked up our bags after checkout so that we could walk around before our flight. And then he came and met us where we were to run us to the airport-it was fantastic! The property is great, albeit a 10-20 min walk to some places. That said, the quiet was great and the Tipsy Rooster across the street alwyas had great live music at night! It was a great fit for us, although...
The price is AED 555
AED 1,363 total
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 AED 1,030
AED 2,920 total
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, (77)
"Easily walkable to most tourist attractions."
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!

9.8 out of 10, Exceptional, (9)
"Wonderful location, communication & overall experience "
The price is AED 555
AED 1,341 total
includes taxes & fees
14 May - 15 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, (155)
"This property is in a great spot. Easy access to anywhere in KeyWest. Super clean will stay here again. "
Conch Republic Consul General's Cottage.-Historic District
One Bedroom Cottage House in Old Town Key West by the Hemingway House.
Fridge, microwave, oven, stovetop

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

6.0 out of 10, (2)
~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, (11)
"This property was exactly what we had hoped for. It was close to the water and trolley stop, which made it very easy to get around and see the sights. The property was clean and nicely landscaped and although we were close to the activities it felt very private and secluded when we were on property.The management staff was extremely helpful and responsive. Street parking on-site was a little pricey (6.00/hr), so we parked at the rental office a few miles away and the staff shuttled us around....
The price is AED 555
AED 1,356 total
includes taxes & fees
23 Apr - 24 Apr
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)
"Great spot. Very quiet and clean. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
TV, stereo

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

9.4 out of 10, Exceptional, (218)
"Very nicely located to walk or uber everywhere"
The price is AED 771
AED 1,780 total
includes taxes & fees
29 Apr - 30 Apr
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!

10.0 out of 10, Exceptional, (8)
"We enjoyed our stay at this quaint property. It was walkable to many area attractions including Hemingway House and Zachary Taylor State Park. The property was clean and had what we needed for the two nights we were visiting. "
The price is AED 555
AED 1,341 total
includes taxes & fees
14 May - 15 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)
"Well kept"
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, (12)
"Everything was great. A little noisy from across the street, but hey it's Key West :) "
The price is AED 555
AED 1,363 total
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, (2)
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, (217)
"We so enjoyed our stay at Chick-A-Pea cottage. We spent time chatting in the cabana or lounging by the pool most of the time we were "home". The cottage is in a great location, half a block off Duval Street - lots of places within walking distance. Fun time had by all! "
~ 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
Deluxe Bungalow | Private kitchen

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (128)
"It was a great experience being on a houseboat."
The price is AED 405
AED 1,071 total
includes taxes & fees
27 Apr - 28 Apr
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Terrace/patio

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (292)
"We both loved the place. Great location, room was awesome, the pool was fun and staff was very friendly and helpful. "
The price is AED 1,155
AED 1,403 total
includes taxes & fees
19 Apr - 20 Apr
Hyatt Vacation Club at Sunset Harbor, Key West
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, (119)
"This cottage was amazing for so many different reasons. Location, quiet, and detail to guests needs. Marcela was a great communicator. No need to communicate too much, everything worked great! We are returning next year!"
Heart of Downtown Key West Cottage With Off-Street Parking
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.