A sunset over a beach with a wooden pier and a small structure on it.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Cow Key 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.
$682 nightly
The price is $757
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.

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, (152 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
$739 nightly
The price is $820
Nov 1 - Nov 2
Total with taxes and fees
The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!
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 Cow Key Hotel Reviews

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"Great place."
Craig 2-night trip
Posted less than an hour ago
The Southernmost Inn - Adults Only

Find out more about Cow Key

Cow Key Cottages information

Number of reviews
188
Accommodation
153 Cottages
Lowest Price
$757
Highest Price
$820

Frequently asked questions

How much do cottages in Cow Key cost?
Cottages in Cow Key range between $757 and $820 per night. These properties offer a chance to get reacquainted 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 Cow Key?
Cow Key offers multiple cottages with a total average guest review rating of 9.9. Simonton Court Cottages is a superb option if you like natural surroundings and an unhurried pace. Travelers staying at this 3-star stay will have use of WiFi and pet-friendly facilities. Casa Manana Key West Monthly: 2 Br is another popular choice. This 3-star cottage has a swimming pool and a barbecue grill.
How many cottages are there in Cow Key?
Reconnect with nature in one of the 153 cottages on offer in Cow Key. To help you reserve your ideal stay, use our filter tool to search for perks or amenities you need.
Are there any family-friendly cottages in Cow Key?
Many travelers needing a family-friendly cottage in Cow Key choose Simonton Court Cottages. With a 3-star rating and amenities including housekeeping services and WiFi, it'll feel like your home away from home. Another excellent option for traveling families is Casa Manana Key West Monthly: 2 Br. An oven and a king-sized bed help make this 3-star cottage a comfy base for your Cow Key trip. Once you've checked in and dropped off your things, there's no shortage of family-friendly attractions to visit in and around Cow Key. Smathers Beach and South Beach are two of our top suggestions.
Why book your cottage in Cow Key with Expedia?
Expedia has some wonderful cottages in Cow Key, so start packing for a memorable vacation on nature's doorstep. If you have a budget in mind, click on how much you'd like to spend and your preferred property star rating. Or, make your way to the filters to search for cottages with a pool or a hot tub. We'll help you find the right place whatever your plans or style of travel.
How can I find cheap cottages in Cow Key?
A great way to locate cheap cottages in Cow Key is with Expedia's handy filter tool. Fine-tune your search results by amenities, star rating and budget to access unbeatable deals with only a few clicks.

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