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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Key West cottages

A building with a white exterior, a brick pathway, and lush greenery including palm trees and flowering plants.

1. Get your ISLAND STLYE on!

Get your ISLAND STLYE on!
Old Town Key West
9.6 out of 10, Exceptional, (85 reviews)
"Good location. Provided everything that was listed. The unit was very clean."
United States
Mary S.
$630 nightly
The price is $689
Nov 9 - Nov 10
Total with taxes and fees
Get your ISLAND STLYE on!
A two-story building with balconies, surrounded by lush greenery and palm trees.

2. 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.
$698 nightly
The price is $775
Nov 15 - Nov 16
Total with taxes and fees
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.

3. 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, (153 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
$750 nightly
The price is $833
Nov 1 - Nov 2
Total with taxes and fees
The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!
A small, single-story building with a white exterior and a metal roof, surrounded by lush greenery and a paved patio area.

4. Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (23 reviews)
"Great location, clean and well equipped."
United States
Richard M.
$714 nightly
The price is $783
Nov 3 - Nov 4
Total with taxes and fees
Find your zen at HIDDEN TREASURE
A stationary houseboat with a covered deck, named 'Aqua Lodge', featuring a lounge area with chairs and tables.

5. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (378 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
$223 nightly
The price is $251
Oct 30 - Oct 31
Total with taxes and fees
Old Wooden Bridge Resort and Marina
A balcony with a view of the sea and a distant shoreline.

6. 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.
$583 nightly
The price is $628
Nov 8 - Nov 9
Total with taxes and fees
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

8/10 Good
"Their ad says shuttle service within 8 miles of the resort, but really the shuttle went to only 1 spot in town. Luckily, Uber is quick and relatively cheap. The restaurant on the property is OK, but nothing to write home about. Thank goodness for the Starbucks on site. If you don't mind loud music, then a poolside room is for you. If you prefer it a little quieter, then get a room overlooking the road. The elevators take FOREVER to arrive, and we took the stairs most of the time. Aside from those issues, it is a very nice place, and the staff were very friendly and helpful."
patricia 5-night trip
Posted 7 hours ago
Blue Flamingo Resort Key West

Find out more about Key West

Key West Cottages information

Number of reviews
708
Accommodation
110 Cottages
Lowest Price
$251
Highest Price
$833

Frequently asked questions

How much do cottages in Key West cost?
Cottages in Key West range between $251 and $833 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?
Select from multiple cottages in Key West with a total average guest review rating of 9.5. Simonton Court Cottages is an ideal place to rest your feet between adventures. This 3.5-star cottage also comes with a garden and a nearby beach. Casa Manana Key West Monthly: 2 Br is another leading option with visitors in this area. It has a 3-star rating and amenities including a king-sized bed and a swimming pool.
How many cottages are there in Key West?
Stay in touch with nature in one of the 110 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?
A trip with the family in Key West is simple at Casa Manana Key West Monthly: 2 Br. With amenities including a king-sized bed and a barbecue grill, you'll find all the comforts of home at this 3-star cottage. Simonton Court Cottages is another family-friendly stay where you and your squad can escape the hustle and bustle of city life. This cottage has a 3-star rating and amenities including housekeeping services and WiFi. Key West boasts plenty of family-friendly attractions to check out that'll entertain the kids. Smathers Beach and South Beach promise a fun day out for both young and old.
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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