Search Cow Key Cottage Rentals from CA $134

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Cow Key Cottages

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Enjoy a serene outdoor space surrounded by lush plants and a charming seating area.

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

10.0 out of 10, Exceptional, (16)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is CA $134
CA $463 total
includes taxes & fees
Aug 5 - Aug 6
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Waterfront Home
Enjoy a serene canal view from this balcony with seating for two.

Waterfront Home

8.8 out of 10, Excellent, (167)
"Great price great location "
Waterfront Home
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

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

10.0 out of 10, Exceptional, (1)
"Easy walk to everything! Comfortable stay. "
The price is CA $326
CA $677 total
includes taxes & fees
Aug 14 - Aug 15
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Canal front, dockage, 2 bedroom, 2 bath
Enjoy a waterfront retreat with a balcony overlooking the water, a covered outdoor area, and access to the dock.

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (85)
"The place was everything as described. Close enough to Key West and beaches that we did not stay home much during the day but nice to have a peaceful place to land in the evenings. Bedrooms and bathrooms were right but served its purpose. Jennifer and Susan were very helpful with check in. Thanks for letting my parents relive their glory days in the Keys. I would stay again if we come back!"
Canal front, dockage, 2 bedroom, 2 bath
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Relax in a serene oasis with a hot tub surrounded by lush tropical plants and a wooden fence.

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

10.0 out of 10, Exceptional, (18)
"Will stay here again "
The price is CA $134
CA $463 total
includes taxes & fees
Aug 10 - Aug 11
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Conch Republic Consul General's Cottage.-Historic District
Surrounded by lush greenery, this charming house features a white picket fence and a welcoming front door.

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (161)
"Cute, charming, clean and quiet. Great location. "
Conch Republic Consul General's Cottage.-Historic District
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Guests can enjoy a peaceful stay in this charming single-story building surrounded by a beautifully maintained garden.

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

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is CA $134
CA $460 total
includes taxes & fees
Aug 12 - Aug 13
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Relax in a secluded outdoor space with a hot tub surrounded by lush tropical plants and trees.

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

9.6 out of 10, Exceptional, (22)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
The price is CA $134
CA $461 total
includes taxes & fees
Aug 17 - Aug 18
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Heart of Downtown Key West Cottage With Off-Street Parking
Cozy home with a front porch and garden, perfect for relaxation.

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking
waterfront cottage near key west, sleeps 6
Enjoy the serene marina view from the comfort of your room, featuring a spacious seating area and large windows.

waterfront cottage near key west, sleeps 6

9.4 out of 10, Exceptional, (22)
"This place is exactly as described. The quirkiness was perfect for my husband and I to spend our anniversary. We had a day of rain and it was perfect!and"
waterfront cottage near key west, sleeps 6
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Stroll through the serene garden, surrounded by lush palm trees and vibrant greenery, leading to a charming porch.

Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking

9.2 out of 10, Wonderful, (74)
"Really nice property just as the photos had everything we needed, great surroundings with character the pool area was perfect and well kept a very relaxing and friendly environment . The attached history to the Conch Republic was very interesting and maintained. Communications with Roberta were again very easy and in a timely & friendly manner Easy walk to Duval st and other attractions. All in all a great place to stay and would highly recommend "
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Enjoy a romantic meal with a serene view of the marina and calm waters.

**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

9.6 out of 10, Exceptional, (38)
"Property was very clean and well stocked. Perfect location on the water. Would definitely rent again "
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
One Bedroom Cottage House in Old Town Key West by the Hemingway House.
Cozy home with a gabled roof and inviting front porch, perfect for relaxing.

One Bedroom Cottage House in Old Town Key West by the Hemingway House.

One Bedroom Cottage House in Old Town Key West by the Hemingway House.
Cottage with Pool and Dockage, just minutes to Key West
Residential homes with unique architectural styles surround a large pool and well-manicured lawn.

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (149)
"Good Fishing, Good local eateries. "
The price is CA $380
CA $658 total
includes taxes & fees
Aug 5 - Aug 6
Cottage with Pool and Dockage, just minutes to Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Detached houses with individual driveways and yards surround a swimming pool area adjacent to the beach.

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

9.0 out of 10, Wonderful, (49)
"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Stroll through the charming front porch, surrounded by lush tropical plants and a picket fence, to the inviting entrance with a glass door.

Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex

10.0 out of 10, Exceptional, (196)
"Had another wonderful week at Sea Breeze Cottage. Perfect home, location, amenities, and host. Love going there. "
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Find your zen at HIDDEN TREASURE
Charming cottage with a front porch and lush green surroundings.

Find your zen at HIDDEN TREASURE

3.0 star property
9.6 out of 10, Exceptional, (9)
"The property and location is great! The private deck was awesome. "
Find your zen at HIDDEN TREASURE
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Relax on the beach with lounge chairs and a tranquil sea view.

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

8.8 out of 10, Excellent, (72)
"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "
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
Enjoy scenic views of the ocean and surrounding landscape from this coastal property featuring a pool, residential buildings, and a lush garden with palm trees.

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

9.0 out of 10, Wonderful, (85)
"My husband and I stayed with our son in the cottage and it was everything we needed. Great location, beautiful pool on the water, and just enough space. "
The price is CA $346
CA $640 total
includes taxes & fees
Aug 2 - Aug 3
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Relax in this serene outdoor seating area with a comfortable sofa, a small table, and a chair, surrounded by lush greenery and a beautiful beach scene.

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

3.0 star property
10.0 out of 10, Exceptional, (3)
"Our second time staying here. Great location. Everything you would need for a couple. Clean,comfortable. Will rent again if available next year."
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cow Key Hotel Reviews

Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

10/10 Excellent
"Good hotel and people friendly. The area is super nice "
Juan 2-night trip
Posted 13 hours ago
Fairfield Inn and Suites by Marriott Key West