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

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (214)
"Very clean. Could use some updating such as fresh paint. "
The price is AED 591
AED 1,603 total
includes taxes & fees
26 Nov - 27 Nov
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Main Entrance off Street - Peaceful and Quiet!
Southernmost Retreat: 2 Blocks from Duval in Old Town.
10.0 out of 10, Exceptional, (106)
"Key West after fantasy week we had a great time manager always got right back to us"
The price is AED 1,837
AED 3,027 total
includes taxes & fees
24 Nov - 25 Nov
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Conch Republic Consul General's Cottage.-Historic District
Conch Republic Style Swimming Pool.
Conch Republic Consul General's Cottage.-Historic District
9.4 out of 10, Exceptional, (149)
"Very clean and well equipped kitchen although we didn’t cook! Quiet neighborhood but not far from everything! Pool was very nice and relaxing!"
Conch Republic Consul General's Cottage.-Historic District
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior detail
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.0 out of 10, Very Good, (29)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Front of Cottage
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
10.0 out of 10, Exceptional, (179)
"The property is great location. Nice and clean. We really enjoyed stay. Pillows would be the only negative feedback. Need some softer ones."
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Lots of sitting including lounge chairs and table and chair sets
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
9.2 out of 10, Wonderful, (69)
"This quaint little bungalow has everything you need. We walked about 21 miles overall during our 8 day stay but we were able to see so many amazing things. We went fishing, went on a sunset cruise, walked to several of the museums. We were Awed by the rich history. I think we actually ate our way through Key West and still had a few meals in the bungalow. Oh did I mention the almost private pool. We loved that, after a long day walking we would come back and soak in the pool for a while. We...
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
waterfront cottage near key west, sleeps 6
pools, a spa and the ocean, what more do you need?
waterfront cottage near key west, sleeps 6
9.4 out of 10, Exceptional, (16)
"We had a great stay! Other than the weather, everything was perfect! We had plans to dock our boat up at the house but it was too windy to take the boat out. We still enjoyed the patio and grilled out one night! We took showers across the street at the camp restrooms bc there were four of us and we would’ve ran out of hot water but that was no problem. We enjoyed our stay!"
waterfront cottage near key west, sleeps 6
Old Town Cottage House in Old Town Key West!
Living area
Old Town Cottage House in Old Town Key West!
Old Town Cottage House in Old Town Key West!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (62)
"We are old Florida Keys visitors and past residents. We were delighted with the accommodations, pool and view.We are planning our next stay...same time, same place minus the two days of Helene.Will have to make arraignments for a recliner to be delivered for my wifes sleeping and sitting comfort.Our first night was Sept 20 not the 19th as indicated in error. We stayed 9 nights.Thanks again for the great stay!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Mind - Venture Out Unit 225
Blue Mind - Venture Out Unit 225
9.4 out of 10, Exceptional, (66)
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Welcome to Tidewater Views...
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
10.0 out of 10, Exceptional, (200)
"Great little place on the water especially if you are bringing a boat. The house was perfect! It was my birthday and our host Charity even got me a birthday cake and card. We will definitely be back!! "
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior detail
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (53)
"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
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Chick-a-Pea Cottage has an amazing pool with waterfall!
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
10.0 out of 10, Exceptional, (206)
"The house was perfect in every way for us….. 2 married couples. The communication with property manager was beyond superb. Although a few steps from Duval, was a very quiet location. Highly recommend. "
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Pool
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
3.5 star property
8.0 out of 10, Very Good, (2)
"The living room furniture and mattresses are not the most comfortable. Worn. Mattresses in small bedroom need replacement. Air conditioner does not reach small bedroom. "
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
Living area
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
3.0 star property
10.0 out of 10, Exceptional, (1)
"There are 3 things I would say could and should be better. 1) extra toilet paper. There was only one partial roll in each bathroom and one extra partial roll. 2) no shampoo/conditioner. 3) no directions to the pool. I had to call and find out where it was. For the amount you pay, you’d think those items would be available as there are everywhere else I’ve stayed. "
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
OSPREY STUDIO @ The Colony-Sleeps up to 4
Osprey @ Colony
OSPREY STUDIO @ The Colony-Sleeps up to 4
2.0 star property
9.6 out of 10, Exceptional, (48)
"Great experience. Will recommend. "
OSPREY STUDIO @ The Colony-Sleeps up to 4
Find your zen at HIDDEN TREASURE
Hidden Treasure @ Colony
Find your zen at HIDDEN TREASURE
3.0 star property
Find your zen at HIDDEN TREASURE
ROYAL POINCIANA COTTAGE - Quaint Old Town location
Royal Poinciana @ Conch Cottages view from street
ROYAL POINCIANA COTTAGE - Quaint Old Town location
2.0 star property
9.4 out of 10, Exceptional, (35)
"Exactly what we wanted! Lush tropical setting close to everything but quiet. We will be back"
ROYAL POINCIANA COTTAGE - Quaint Old Town location
FL Keys Cottage with Ocean Views - Venture Out Unit 395
FL Keys Cottage with Ocean Views - Venture Out Unit 395
8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Miscellaneous
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
9.8 out of 10, Exceptional, (8)
"Our stay was amazing. The property was immaculate. The amenities were great. We will be back next year. The location was perfect. Close to Key West and alot to do in the area. Thank you for making our stay wonderful. See you next year!"
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
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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Other property types in Cow Key

Aqua Lodges at Hurricane Hole Marina
Exterior
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is AED 493
AED 1,060 total
includes taxes & fees
3 Dec - 4 Dec
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Pool
Steps from Duval, Pool on Site & Bikes Included!
9.6 out of 10, Exceptional, (356)
"We walked most everywhere and loved the Southernmost Beach Bar! Eating at Moon Dog Cafe was so spectacular that we ate there 3 times in 2 days! This place is all it says it is. Simply perfect. "
The price is AED 364
AED 876 total
includes taxes & fees
2 Dec - 3 Dec
Steps from Duval, Pool on Site & Bikes Included!
Poolside Cottage #411
Pool
Poolside Cottage #411
10.0 out of 10, Exceptional, (30)
"Nice STAY"
The price is AED 826
AED 1,398 total
includes taxes & fees
2 Dec - 3 Dec
Poolside Cottage #411
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.

Frequently asked questions

How much do cottages in Cow Key cost?
Cottages in Cow Key range between AED 591 and AED 1,837 per night. These retreats offer a chance to soak in nature’s beauty — 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 9.3. Simonton Court Cottages is a fantastic option if you love nature and a relaxing pace. Visitors staying at this 3.5-star stay can enjoy conveniences such as WiFi and pet-friendly facilities. Casa Manana Key West Monthly: 2 Br is another popular pick. This 3-star cottage features a king bed and a swimming pool.
How many cottages are there in Cow Key?
Pick from 123 cottages in Cow Key. Whether you’re vacationing with the kids or planning a weekend retreat with your best buds, Expedia can help you find the ideal place to enjoy nature’s beauty.
Why book your cottage in Cow Key with Expedia?
Reserving a cottage in Cow Key is as simple as deciding on your travel dates and choosing your ideal place for a vacation in nature. From ritzy retreats to inexpensive properties and cottages that include conveniences like a kitchen, Expedia has something for all styles and tastes. As for terrific deals? We’ve got them as well!
How can I find cheap cottages in Cow Key?
Expedia can help you easily track down cheap cottages in Cow Key. To find your perfect stay in a couple of quick clicks, try out the filter tool to tailor your search results by budget, amenities and star rating.