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Our top choices for Cow Key cottages

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (52 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
$382 nightly
The price is $425
Jan 20 - Jan 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (157 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
$286 nightly
The price is $317
Jan 21 - Jan 22
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (161 reviews)
"We love our little cudjoe key hideaway"
United States
Mary H.
$398 nightly
The price is $442
Jan 22 - Jan 23
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (176 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
$381 nightly
The price is $423
Jan 29 - Jan 30
Total with taxes and fees
Waterfront Home

Beautiful Cottage & Amenities in Gated Community

Beautiful Cottage & Amenities in Gated Community
Cudjoe Key
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
$619 nightly
The price is $687
Jan 27 - Jan 28
Total with taxes and fees
Beautiful Cottage & Amenities in Gated Community

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (91 reviews)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
$440 nightly
The price is $488
Feb 1 - Feb 2
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very Good, (55 reviews)
"Great area. Quiet and comfortable "
United States
nancy c.
$357 nightly
The price is $396
Jan 20 - Jan 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
2.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (54 reviews)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
$640 nightly
The price is $701
Feb 3 - Feb 4
Total with taxes and fees
OSPREY STUDIO @ The Colony-Sleeps up to 4

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Old Town Key West
9.8 out of 10, Exceptional, (29 reviews)
"Loved this little place "
United States
Charles N.
$474 nightly
The price is $522
Jan 20 - Jan 21
Total with taxes and fees
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Living Life Dockside

Living Life Dockside
Stock Island
10.0 out of 10, Exceptional, (1 review)
"The hosts, Glen and Abby were super sweet. Glen even made a spaghetti dinner to share amongst all the incoming guests. The available kayaks and paddle boards were fabulous! We will be back for sure! "
United States
Angela H.
$558 nightly
The price is $620
Jan 20 - Jan 21
Total with taxes and fees
Living Life Dockside

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (121 reviews)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
United States
ANJANA
$337 nightly
The price is $375
Jan 20 - Jan 21
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West

Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (147 reviews)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$393 nightly
The price is $437
Jan 20 - Jan 21
Total with taxes and fees
Quaint cottage, pool, dockage just minutes to Key West!

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (76 reviews)
"Place was everything we needed, would definitely stay again "
United States
James h.
$382 nightly
The price is $425
Jan 20 - Jan 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Old Town Key West
9.8 out of 10, Exceptional, (23 reviews)
"Great little place, perfect for southernmost area."
United States
Lee G.
$477 nightly
The price is $525
Jan 21 - Jan 22
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (36 reviews)
"Good place to stay loved it"
United States
Charles I.
$474 nightly
The price is $522
Jan 20 - Jan 21
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Old Town Key West
10.0 out of 10, Exceptional, (31 reviews)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
$514 nightly
The price is $565
Jan 26 - Jan 27
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Old Town Key West
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
$474 nightly
The price is $522
Jan 20 - Jan 21
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (11 reviews)
"Great place to stay! "
United States
sarah R.
$1,020 nightly
The price is $1,123
Feb 2 - Feb 3
Total with taxes and fees
Find your zen at HIDDEN TREASURE

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (27 reviews)
"Safe location. Clean room and comfortable beds."
United States
Billie W.
$626 nightly
The price is $688
Feb 4 - Feb 5
Total with taxes and fees
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from 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

Find out more about Cow Key

Cow Key Cottages information

Number of reviews
1,227
Accommodation
169 Cottages
Lowest Price
$317
Highest Price
$1,123

Frequently asked questions

How much do cottages in Cow Key cost?
Cottages in Cow Key range between $317 and $1,123 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 9.1. 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 169 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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