A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Key West cottages

A two-story building with balconies, surrounded by lush greenery and palm trees.

1. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful property! We enjoyed our stay! Property hosts were very attentive to every question we had. Highly recommend!"
United States
Sheri J.
The price is £520
includes taxes & fees
15 Nov - 16 Nov
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
A two-story building with balconies, surrounded by lush greenery and palm trees.

2. The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!

The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!
Old Town Key West
9.8 out of 10, Exceptional, (154 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
The price is £632
includes taxes & fees
12 Nov - 13 Nov
The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!
A floating houseboat with a covered deck and seating area, docked at a marina.

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is £163
includes taxes & fees
4 Dec - 5 Dec
Old Wooden Bridge Resort and Marina
A balcony with white chairs and a table, overlooking a canal with houses and palm trees.

4. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
8.8 out of 10, Excellent, (190 reviews)
"Porsche Berry Duty"
United States
Rafael G.
The price is £265
includes taxes & fees
26 Nov - 27 Nov
Canal Front home with easy Ocean access
A balcony with a view of the sea and a distant shoreline.

5. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (33 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
The price is £360
includes taxes & fees
8 Nov - 9 Nov
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
A covered outdoor deck with a sofa and table, overlooking a marina with boats and palm trees.

6. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (110 reviews)
"Exactly as shown in the pictures and as described. Appreciated the extra location for the boat trailer."
United States
Laurie C.
The price is £398
includes taxes & fees
14 Nov - 15 Nov
Canal front, dockage, 2 bedroom, 2 bath
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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Top Key West Hotel Reviews

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"The property was very nice,well maintained and easily accessible. The staff were very accommodating. I woukd definitely stay here again."
Steve 1-night trip
Posted 2 hours ago
The Perry Hotel & Marina Key West

Find out more about Key West

Key West Cottages information

Number of reviews
903
Accommodation
114 Cottages
Lowest Price
£163
Highest Price
£632

Frequently asked questions

How much do cottages in Key West cost?
Cottages in Key West range between £163 and £632 per night. These retreats offer a chance to touch base with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Key West?
A guest favourite is Simonton Court Cottages. Base yourself at this 3.5-star stay which offers a garden and WiFi. Simonton Court Cottages is another popular option worth shortlisting. Unpack your suitcase at this 3-star cottage and make the most of conveniences like WiFi and a fridge. You'll have your pick of multiple cottages in Key West with a total average guest review rating of 9.3.
How many cottages are there in Key West?
Stay in touch with nature in one of the 114 cottages waiting for you in Key West. To help you choose an ideal property, make use of our handy filters to search for must-have perks or amenities.
Are there any family-friendly cottages in Key West?
Get comfortable at Casa Manana Key West Monthly: 2 Br, a 3-star cottage not far from downtown. Conveniences here include clothes washing facilities and a king-sized bed. Another family-friendly option where you can swap the urban jungle for wide open spaces is Simonton Court Cottages. WiFi and housekeeping services help make this 3-star cottage a guest favourite. Once you've checked in and dropped off your bags, there's a host of family-friendly attractions to see around Key West. Clarence S. Higgs Memorial Beach Park and Duval Street promise fun for all ages.
Why book your cottage in Key West with Expedia?
We think a getaway should be simple, so if you're seeking cottages in Key West at the perfect price, Expedia has you covered. Keep the budget in check and check in to a cheap option far from the hustle and bustle, or splurge on a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Key West?
A good way to spot cheap cottages in Key West is with Expedia's handy filter tool. Tailor your search results by amenities, star rating and budget to land unbeatable deals in a couple of clicks.
What is there to do in Key West near my cottage?
Key West has enough experiences and activities to keep you amused for weeks, starting with Nancy Forrester's Secret Garden. Donkey Milk House, Clarence S. Higgs Memorial Beach Park and Duval Street are other wonderful attractions. If you have more time, Smathers Beach and Mallory Square will add the finishing touches to your itinerary.

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