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Key West, Florida, United States of America

Key West cottage rentals

We found 105 cottages — enter your dates for availability

Explore Key West cottage rentals

ELIZABETH'S SECRET - 2/2-Old Town WEEKLY vacation rental-Private pool-Parking

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$668 avg/night
(128)

Heart of Downtown Key West Cottage With Off-Street Parking

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$393 avg/night
(16)

Atlantis House's Garden Suite-voted top 25 in USA

Sleeps 2 · 1 Bedroom · 1 Bathroom
$292 avg/night
(66)

~POPPY COTTAGE~ Cute Home In Quiet Location

Sleeps 2 · 1 Bedroom · 1 Bathroom
$143 avg/night
(8)

Southernmost Retreat: 2 Blocks from Duval in Old Town.

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$484 avg/night
(29)

Cozy cottage w/ porch & great walking location - close to beach, small dogs OK!

Sleeps 4 · 1 Bedroom · 2 Bathrooms
$398 avg/night
(145)

Search 105 cottages

Recent reviews of Key West cottage rentals
Stayed Oct 2021

Great spot to enjoy key west!

This property was great. Everything was clean and well stocked. Beach towels provided and comfy beds! The complex was super convenient, safe and clean. Parking can be a bear. CVS is literally 1 block away for anything you need. They have paid laundry...

Lee T.
Lee T.
Stayed Oct 2021

Great location!

Great little place in a great location just a block off Duval. Scott and Natalie were more than accommodating and very attentive to any questions I had. Parking was a little tricky but it's Key West so that was to be expected. We had a great weekend!...

Michele H.
Michele H.
Stayed Oct 2021

PERFECT house for our Key West stay!

Fleming-O was PERFECT for our Key West stay. This house is waaaaay roomier inside than the photos depict. We slept 6 easily (grandparents in the queen bed room, my wife and I in the double twin-beds room, and our two teenagers on the living room's pu...

Chad C.
Chad C.
Stayed Oct 2021

The Heart Of Key West

1st class accommodations, great set up for 2 couples and the host thought of everything including the best key lime pie in town. Property is tucked away safe and sound yet in the heart of town yet quiet. If we had known about the exterior security ca...

Maureen O.
Maureen O.
Stayed Sep 2021

Great location and very nicely remodeled!

We had a great time for our first stay in the Keys! The hot tube was a nice addition to the stay! Being enclosed was very nice and gave us privacy. We did go to the adult pool but unfortunately had children having fun, which was nice they were but, l...

Timothy B.
Timothy B.

Madeira Beach

Stayed Sep 2021

Great location, great property

We loved our stay at Chick-a-Pea! The location is literally right off Duval, can't get better than that. All the amenities and kitchen supplies you would ever need. The pool and deck was by far our favorite part, felt very secluded and private. Only ...

Brittany C.
Brittany C.
Stayed Sep 2021

Cozy house in a perfect location

This house was the perfect place for ladies weekend with 3 of us. The location was perfect and steps away from Duval but tucked away with a perfect backyard to relax and avoid the crowds when we felt like it. The property was clean and check-in was e...

Heidi C.
Heidi C.
Stayed Sep 2021

An above average home in KW, with a great location

This was my 4th stay in KW and loved the location of this property. It was gated with a huge front yard to safely park your bikes or scooters. The house was just big enough for our group, with a nice kitchen and living room space to gather everyday. ...

Kandyce K.
Kandyce K.
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