Search Cow Key Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 123 Cottages in Cow Key with updated reviews, rates, and availability.

Southernmost Retreat: 2 Blocks from Duval in Old Town.
Beach nearby
Southernmost Retreat: 2 Blocks from Duval in Old Town.
10.0 out of 10, Exceptional, 98 reviews
"Walking close to Duval. On street parking can be tough but this block is NOT pay to park! Good to know."
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, 53 reviews
"It was a nice Key West cottage with beautiful views of Cudjoe Bay."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, 201 reviews
"We stayed in cabin 6 for a week. Management was very helpful. The cabin had everything we needed. Very comfortable bed and the 2 baths were definitely a plus. Great location. Within walking distance to everything. We did rent a golf cart and parking was never a problem. We are planning our next trip and will stay here again."
The price is $217
$512 total
includes taxes & fees
Jun 24 - Jun 25
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
A heated pool
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
10.0 out of 10, Exceptional, 14 reviews
"Excellent concept. Loved this unit. Very clean. Only had one small glitch when checking in because I don't text. The lady who manages the unit was exceptional. Wished I could find employees like her."
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.2 out of 10, Very Good, 27 reviews
"This place was nice. The pool situation was a little awkward as it does appear to be mainly for the bigger house as other reviews stated. The gas grill which is beneath the main house by the pool is communal. The main reason I gave this a 4 was because the smoke alarms in the rental did not have any batteries. Everything else was as described."
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
Beach
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, 34 reviews
"This property is super cute. Convenient for being close to Key West without the price of Key West. We VERY much enjoyed our 3 night stay. Our property (#15) had a little grill outside so we were able to cookout one night of our stay. Make sure you stop at Publix or Winn Dixie before getting there it is a litle trek to get to grocery store. I would also suggest bringing a few extra bath towels, our cottage only had 3 and 4 adults. Most things you would need, pots, pans, silverware, cups, coffee...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Town Cottage House in Old Town Key West!
Exterior
Old Town Cottage House in Old Town Key West!
Old Town Cottage House in Old Town Key West!
Waterfront Home
Exterior
Waterfront Home
8.8 out of 10, Excellent, 141 reviews
"Would definitely come back!!!!"
Waterfront Home
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Property grounds
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
10.0 out of 10, Exceptional, 9 reviews
"Perfect size for a couple. New and clean, couldn’t be happier, thanks!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Exterior
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
10.0 out of 10, Exceptional, 119 reviews
"Perfect location. Everything you need. Nice decor. Very quiet. Alice was very helpful. My only complaint is not being allowed in the huge pool that sat unused the whole time we had to walk by it to get to our rooms. It was hot while we were there and it would have been hospitable."
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Pool | A heated pool
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
10.0 out of 10, Exceptional, 195 reviews
"This beautifully decorated property is centrally located but feels secluded. The beds are incredibly comfortable and the pool was perfect for relaxing. It was perfect for our girls' weekend. The property manager was attentive and helpful. We would definitely stay here again."
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.0 out of 10, Wonderful, 34 reviews
"This is the second time my son and i have stayed in these cottages. Basic and comfortable and in a good location."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Mind - Venture Out Unit 225
Property grounds
Blue Mind - Venture Out Unit 225
9.6 out of 10, Exceptional, 64 reviews
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Property grounds
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
9.6 out of 10, Exceptional, 28 reviews
"Great location and beautiful views!"
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, 65 reviews
"Resorts was great love the pool and water....home was clean nice bedrooms and baths really small but we just sleep in them. Deck was great. To be in early morning watching sun rise..."
Canal front, dockage, 2 bedroom, 2 bath
Conch Republic Consul General's Cottage.-Historic District
Pool
Conch Republic Consul General's Cottage.-Historic District
9.4 out of 10, Exceptional, 139 reviews
"Our stay was for a week and we had the best time. Walking distance to Duval Street was definitely a plus. The on site pool was wonderful to come back to after a day out in the sun. The property owners, who lived right there, were the best hosts and very hospitable. Highly recommend this property and would definitely revisit."
Conch Republic Consul General's Cottage.-Historic District
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, 51 reviews
"The grounds are good. The pools were clean and plenty of deck and dock space. The cottage itself needs help. It needed general maintenance on it. It needs caulking in the bathroom. It needs weather strips around door as it is not tight. There was not enough hand towels and there are no oven mitts in the kitchen. The exhaust fan has been taken out. The ceiling fan in one room only works on high. The ac vents and exhaust fan in the bathroom needs cleaning. We were happy about the porch except the...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Lobster Lodge - Venture Out #543
Fridge, microwave, dishwasher, coffee/tea maker
Blue Lobster Lodge - Venture Out #543
9.0 out of 10, Wonderful, 6 reviews
"Great amenities and location."
Blue Lobster Lodge - Venture Out #543
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!
Fridge, microwave, oven, stovetop
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!
10.0 out of 10, Exceptional, 2 reviews
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Property grounds
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
10.0 out of 10, Exceptional, 2 reviews
"This is a nice property. The accommodations were large enough for my family. The indoor space was clean and nicely appointed. The outdoor space was ok. Due to how close the units are together you are right next to your neighbors car when sitting on the patio. The location is about 20 miles from Key West allowing for easy day trips while resting in a quieter location. I would definitely stay here again."
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Don't see what you're looking for?
See all available properties in Cow Key
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.

Other property types in Cow Key

Steps from Duval, Pool & Bikes $129-$299 Night!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, 332 reviews
"Beautiful studio and great location. Communication with the owner was excellent."
The price is $109
$251 total
includes taxes & fees
Jun 20 - Jun 21
Steps from Duval, Pool & Bikes $129-$299 Night!
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, 99 reviews
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is $116
$271 total
includes taxes & fees
Jun 4 - Jun 5
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Aqua Lodges at Hurricane Hole Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, 88 reviews
"Everyone was extremely nice and helpful."
The price is $101
$255 total
includes taxes & fees
Jun 7 - Jun 8
Aqua Lodges at Hurricane Hole Marina
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.

Cow Key Cottages information

Number of reviews
1,021
Accommodation
123 Cottages
Lowest Price
$217
Highest Price
$500

Frequently asked questions

How much do cottages in Cow Key cost?
Prepare to pay between $217 and $500 per night for cottages in Cow Key. Whatever your budget, an epic stay is just a few clicks away on Expedia. This price was 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 9.3. Simonton Court Cottages is a good option if you love nature and an easy-breezy pace. Visitors of this 3.5-star stay can enjoy conveniences like a garden and a nearby beach. Simonton Court Cottages is another popular choice. This 3.5-star cottage has free WiFi and housekeeping services.
How many cottages are there in Cow Key?
Pick from 123 cottages in Cow Key. Whether you’re traveling with the little ones or organizing a weekend retreat with your friends, Expedia will help you find the ideal space to immerse yourself in nature.
Are there any family-friendly cottages in Cow Key?
Get comfortable at Simonton Court Cottages, a 3.5-star cottage not far from town. Amenities here include a nearby beach and free WiFi. Another family-friendly pick where you can swap the urban jungle for nature is Simonton Court Cottages. Housekeeping services and pet-friendly facilities help make this 3.5-star cottage a hit with guests. Once you’ve checked in and unpacked your bags, there’s a host of family-friendly attractions to explore in and around Cow Key. Smathers Beach and South Beach guarantee fun for all ages.
Why book your cottage in Cow Key with Expedia?
We think that a vacation should be a piece of cake, so if you’re looking for cottages in Cow Key at a competitive rate, Expedia has got your back. Save money and stay in a thrifty option far from the rush of the city, or book a luxury cottage to pamper your favorite people.
How can I find cheap cottages in Cow Key?
The easiest way to locate cheap cottages in Cow Key is with Expedia’s user-friendly filter tool. Tailor your search results by budget, star rating and amenities to snag unbeatable deals in a few clicks.
What is there to do in Cow Key near my cottage?
There are tons of impressive things to sink your teeth into in Cow Key. Discover well-known attractions like Smathers Beach, South Beach and Fort Zachary Taylor Historic State Park. Higgs Beach, Key West Aquarium and Boca Chica Nude Beach are other must-see’s.

Recent reviews of Cow Key hotels
Expedia verified reviews

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

5/5 Excellent
"Would definitely stay there again. Nice gem in Key West with a clean marina / plenty of parking."
A verified traveler stayed at The Perry Hotel & Marina Key West
Posted 14 hours ago
The Perry Hotel & Marina Key West