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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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!

9.8 out of 10, Exceptional, (6)
"Great location, very helpful staff "
The price is AED 820
AED 1,715 total
includes taxes & fees
4 Apr - 5 Apr
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, (116)
"This location is great - easy to get to bight and Duval St. The interior was very clean. Good shower, good room lay out, good mattress. Like the two different entrances as I stayed with my sister's family which gave us privacy. Good prompt response from owner and staff. "
The price is AED 1,837
AED 2,991 total
includes taxes & fees
30 Mar - 31 Mar
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!

9.4 out of 10, Exceptional, (8)
"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 621
AED 1,441 total
includes taxes & fees
31 Mar - 1 Apr
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"
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!

10.0 out of 10, Exceptional, (4)
"Located close to many activities. The place was so clean and private. Beds were comfortable. Had everything needed for my visit. Highly recommend staying here."
The price is AED 820
AED 1,719 total
includes taxes & fees
6 Apr - 7 Apr
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, (153)
"Simple checkin and checkout. Clean. Perfect for 2 couples. Each had own bedroom and bathroom. Walkable to all main places in Key West. Nice to have laundry and pool. Really nice to have the parking spot. Great time and would highly recommend. "
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

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)
ROYAL POINCIANA COTTAGE - Quaint Old Town location
A heated pool

ROYAL POINCIANA COTTAGE - Quaint Old Town location

2.0 star property
9.4 out of 10, Exceptional, (39)
"Quaint cottage. Clean with a comfy bed. Well stocked with kitchenware and dishes.Fast wi-fi, nice garden and pool area. Could use a bedside lamp for reading and more shelving in the shower and bathroom. "
ROYAL POINCIANA COTTAGE - Quaint Old Town location
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, (8)
"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 820
AED 1,719 total
includes taxes & fees
6 Apr - 7 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
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (217)
"We have traveled to KW every winter for several years. This place is by far the best combination of location and space. Will be back. "
The price is AED 771
AED 1,761 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, (4)
"Great spot. Did the trick! Lovely time and an excellent porch for chilling."
The price is AED 621
AED 1,438 total
includes taxes & fees
30 Mar - 31 Mar
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

9.6 out of 10, Exceptional, (8)
"We thoroughly enjoyed our time at Caroline’s Cottage. The house is small but everything is laid out perfectly. All the neighbors are very kind and welcoming. Our favorite times were relaxing on the covered porch. While we could not park our car right in front of the house, there was almost always a place to park on the street. There was only one occasion that we had to park a few blocks away. The owners live nearby and were quick to address any concerns that I had (of which there was...
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!

9.4 out of 10, Exceptional, (10)
"We enjoyed the location and staff was very responsive. My preference would have been a more private space but was everything as advertised."
The price is AED 820
AED 1,712 total
includes taxes & fees
1 Apr - 2 Apr
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, (212)
"This was the best vacation house absolutely Pristine clean the outdoor space amazing. The warm pool was perfect excellent location it was a dream vacation for my surprise 60th birthday with my family 7 of us plenty of space !"
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and 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.
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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
8.8 out of 10, Excellent, (123)
"Was amazing, unlike any place i've ever stayed"
The price is AED 608
AED 1,300 total
includes taxes & fees
2 Apr - 3 Apr
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, (290)
"I had a great experience with my family!"
The price is AED 1,414
AED 1,694 total
includes taxes & fees
24 Apr - 25 Apr
Hyatt Vacation Club at Sunset Harbor, Key West
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (376)
"Beautiful place and weather "
Steps from Duval, Pool on Site & Bikes Included!
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.

Frequently asked questions

Why book your cottage in Fleming Key with Expedia?
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How can I find cheap cottages in Fleming Key?
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