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Our top choices for Cow Key cottages

9.2 out of 10, Wonderful, (161)
"Very nice and quiet! "
United States
Lura H.
$397 nightly
The price is $441
Jan 4 - Jan 5
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West
8.6 out of 10, Excellent, (154)
"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 7 - Jan 8
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!
8.6 out of 10, Excellent, (52)
"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.
$386 nightly
The price is $429
Jan 4 - Jan 5
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (164)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
$341 nightly
The price is $379
Jan 4 - Jan 5
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
9.0 out of 10, Wonderful, (89)
"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.
$354 nightly
The price is $393
Jan 5 - Jan 6
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath

Cottage in Cudjoe Key

Waterfront Home
8.6 out of 10, Excellent, (175)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
$400 nightly
The price is $445
Jan 10 - Jan 11
Total with taxes and fees
Waterfront Home
8.2 out of 10, Very Good, (54)
"Great area. Quiet and comfortable "
United States
nancy c.
$361 nightly
The price is $400
Jan 4 - Jan 5
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (121)
"Jennifer was very nice and accommodating."
United States
Randy G.
$341 nightly
The price is $379
Jan 4 - Jan 5
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West
9.0 out of 10, Wonderful, (147)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$397 nightly
The price is $441
Jan 4 - Jan 5
Total with taxes and fees
Quaint cottage, pool, dockage just minutes to Key West!
10.0 out of 10, Exceptional, (25)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
$479 nightly
The price is $527
Jan 7 - Jan 8
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Cottage in Stock Island

Living Life Dockside
$511 nightly
The price is $568
Jan 4 - Jan 5
Total with taxes and fees
Living Life Dockside
10.0 out of 10, Exceptional, (133)
"Great place to stay"
United States
JEFFREY Z.
$746 nightly
The price is $828
Feb 1 - Feb 2
Total with taxes and fees
The Dancing Rooster: 2 Blocks from Duval in Old Town.

Cottage in Old Town Key West

HIDDEN OASIS 3 blocks from Duval
2.5 star property
9.6 out of 10, Exceptional, (96)
"Loved the location of the cottage "
United States
Betty B.
$940 nightly
The price is $1,038
Jan 17 - Jan 18
Total with taxes and fees
HIDDEN OASIS 3 blocks from Duval
9.8 out of 10, Exceptional, (23)
"Great little place, perfect for southernmost area."
United States
Lee G.
$476 nightly
The price is $524
Jan 4 - Jan 5
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
9.8 out of 10, Exceptional, (26)
"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "
United States
Richele
$476 nightly
The price is $524
Jan 4 - Jan 5
Total with taxes and fees
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
9.8 out of 10, Exceptional, (27)
"Great location! Fun place to stay! Responses to our questions/needs very promptly! "
United States
Teressa S.
$476 nightly
The price is $524
Jan 4 - Jan 5
Total with taxes and fees
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
10.0 out of 10, Exceptional, (29)
"It was very cozy to be in after running around in all the chaos of the streets all day"
United States
Sabrina L.
$476 nightly
The price is $524
Jan 4 - Jan 5
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
9.8 out of 10, Exceptional, (36)
"Good place to stay loved it"
United States
Charles I.
$476 nightly
The price is $524
Jan 4 - Jan 5
Total with taxes and fees
Egret Suite | Bright Retreat, 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
1,463
Accommodation
169 Cottages
Lowest Price
$317
Highest Price
$1,038

Frequently asked questions

How much do cottages in Cow Key cost?
Cottages in Cow Key range between $317 and $1,038 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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