Cow Key, FL Cottage Rentals from $379

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

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In two weeks

In two months

In three months

In four months

Our top choices for Cow Key cottages

1. OSPREY STUDIO @ The Colony-Sleeps up to 4

Old Town Key West

Debra S.

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

Old Town Key West

Phyllis B.

$521 nightly

Sep 23 - Sep 24

Total with taxes and fees

3. HIDDEN OASIS 3 blocks from Duval

Old Town Key West

Daniel M.

$553 nightly

Sep 30 - Oct 1

Total with taxes and fees

4. Find your zen at HIDDEN TREASURE

Old Town Key West

Richard M.

$577 nightly

Sep 14 - Sep 15

Total with taxes and fees

5. Canal Front home with easy Ocean access

Cudjoe Key

Lawrence L.

$341 nightly

Sep 9 - Sep 10

Total with taxes and fees

6. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Cudjoe Key

BRIAN S.

$444 nightly

Sep 16 - Sep 17

Total with taxes and fees

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Top Cow Key Hotel Reviews

Blue Flamingo Resort Key West

8/10 Good

"This was an adorable property! There were many things to do."

Southwinds Motel

10/10 Excellent

"Southwinds Motel has to be the absolute best spot I’ve stayed at when it comes to conveniences on site along with an awesome location and proximity to sites and activities. Perfectly located around the Southernmost part of Key West, Southwinds gives you fully stocked bar WITH a built-in liquor store. Super convenient off rip. Bar has live music in the afternoon and evening, a pretty nice pool and deck area and, what I really found most convenient, access to rentals for any means of transportation you need for Key West from bicycles to scooters to full sized golf carts. Rentals are provided by Bone Island rentals who also deliver your mode of moving around to the property and picks it up from the property. A totally ‘Key West’ luxury in my mind. So you’re not staying in the fanciest of shindigs, but you rented a motel because you probably plan to be out and about in beautiful Key West and not cooped up, so you most definitely shouldn’t have grand expectations, but you definitely won’t be disappointed with the digs either. Another thing I really appreciated was after check-in, we were also gifted 2 vouchers for free specialty cocktails from their bar. It was small drinks and only their specialty drinks but still complimentary, so we say thank you and enjoy. They let us combine both tickets for one full sized rum runner my wife enjoyed. Overall 10/10 for comfort, convenience, location and it’s vibe. Will absolutely be going back and 100 percent recommend to all staying in KW"

Beachside Resort & Residences

8/10 Good

"Hot tub wasn’t working. It was just warm water. Gym was very hot. Beach wasn’t great. Elevator in my building wasn’t working g but you can use the one from the building next to it and walk over. So not that bad. Pool was great. Never crowded. Room was excellent. We had a suite with pool access. There was plenty of parking at the hotel and no charge to park We would still go back again."

Find out more about Cow Key

Cow Key Cottages information

Number of reviews	356
Accommodation	154 Cottages
Lowest Price	$379
Highest Price	$631

Frequently asked questions

How much do cottages in Cow Key cost?

Cottages in Cow Key range between $379 and $631 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 9.5. 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 154 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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Key West Vacation Rentals

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Room 1

Check prices for these dates

Our top choices for Cow Key cottages

1. OSPREY STUDIO @ The Colony-Sleeps up to 4