Cow Key Vacation Rentals

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Our top choices for Cow Key vacation rentals

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
Cudjoe Key
8.6 out of 10, Excellent, (79 reviews)
"It was a nice location. 30” from Key West. "
United States
Linda N.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is ¥88,806
¥137,524 total
includes taxes & fees
Mar 24 - Mar 25
Grand Marina Suite by Brightwild Waterfront

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (167 reviews)
"Location was perfect. Oceanfront dock had beautiful sunsets. Oceanfront pool lovely and warm with incredible view. Very friendly vibe and relaxed atmosphere. "
Canada
Jennifer
The price is ¥28,661
¥51,571 total
includes taxes & fees
Mar 26 - Mar 27
Cottage with swimming pool and dockage, just minutes to Key West!

SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (86 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is ¥61,940
¥116,556 total
includes taxes & fees
Apr 3 - Apr 4
SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is ¥174,277
¥299,314 total
includes taxes & fees
Mar 24 - Mar 25
Private and Exclusive Florida Keys Getaway

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (178 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is ¥35,827
¥72,768 total
includes taxes & fees
Mar 29 - Mar 30
Waterfront Home

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (20 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is ¥55,731
¥108,038 total
includes taxes & fees
Apr 13 - Apr 14
Spanish Queen @Venture Out, Cudjoe Key

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveler
The price is ¥127,225
¥272,225 total
includes taxes & fees
Apr 14 - Apr 15
Capmar House at Lunara Bay

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (154 reviews)
"Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. "
United States
Peggy H.
The price is ¥55,731
¥111,103 total
includes taxes & fees
Apr 5 - Apr 6
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (163 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is ¥50,157
¥104,037 total
includes taxes & fees
Mar 25 - Mar 26
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (33 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is ¥63,533
¥117,353 total
includes taxes & fees
Apr 13 - Apr 14
Paradise found

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is ¥77,129
¥99,936 total
includes taxes & fees
Apr 13 - Apr 14
Resort View 1BR Suite With Direct Pool Access

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (145 reviews)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is ¥83,596
¥160,784 total
includes taxes & fees
Apr 11 - Apr 12
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

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

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (28 reviews)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
The price is ¥57,179
¥111,758 total
includes taxes & fees
Apr 19 - Apr 20
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (32 reviews)
"Good condo and staff help me out on phone with me till we found the condo. "
United States
Raamkumaran
The price is ¥78,660
¥111,920 total
includes taxes & fees
Mar 29 - Mar 30
Grand Marina Suite - Poolside & Waterfront Condo

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (54 reviews)
"New furniture, and outfitting. Great view. Possibly the best location in the community. Steps from the boat ramp. "
United States
Matthew K.
The price is ¥62,697
¥144,159 total
includes taxes & fees
Apr 20 - Apr 21
Post Card Point #319 - Ocean Views!

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful "
United States
Lisa P.
The price is ¥71,056
¥144,765 total
includes taxes & fees
Apr 20 - Apr 21
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Meadows
9.8 out of 10, Exceptional, (24 reviews)
"Really enjoyed the accommodations. "
United States
Timothy
The price is ¥69,106
¥133,018 total
includes taxes & fees
Apr 12 - Apr 13
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (41 reviews)
"Our family had a wonderful time at this location. Fishing off the dock and swimming was fun for the kids. A quiet location with a short drive to all attractions."
United States
Nola S.
The price is ¥127,225
¥272,225 total
includes taxes & fees
Apr 22 - Apr 23
Aquaria House at Lunara Bay

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.6 out of 10, Good, (31 reviews)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is ¥42,992
¥84,790 total
includes taxes & fees
Apr 22 - Apr 23
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
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

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Frequently asked questions

Are there vacation rentals in Cow Key?

Yes, we have vacation rentals near well known local attractions in Cow Key, or you can select a more secluded option if you're looking for relaxation. Cow Key is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

What are some of the best vacation rentals that Cow Key has to offer?

Private Secluded Ocean View & Pool Near Key West: You might want to consider this vacation home rental near Cow Key, which is located near the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a hot tub, and foosball so you can immerse yourself in your vacation.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Mel Fisher Maritime Museum, or get out into nature at a spot like Key West Tropical Forest and Botanical Garden. In the larger area, you’ll find Duval Street and Stock Island Yacht Club & Marina.

What are vacation rentals like in Cow Key?

Vacation rentals are private accommodations you can stay in for several days or more in Cow Key. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.