
Holiday houses in Cow Key
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Top-rated holiday rentals in Cow Key
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Other great holiday rentals in Cow Key
Top Guest favourite

Houseboat in Key West
4.95 out of 5 average rating, 20 reviewsShanty Pineapple Key West
BlakeRating, 5 stars3 days ago
Tony was an excellent host! We are locals and did this as a staycation. Beautiful views, and really comfortable space. Highly recommend this spot! The kayak was an awesome addition, there’s a little sandbar and island close by. Would definitely do this again.

Condo in Key West
4.56 out of 5 average rating, 130 reviewsCozy 2BR 3rd-Floor | Pool | Dog Friendly
JrRating, 5 stars2 weeks ago
The place was very nice and cozy. Great location and atmosphere. I would definitely stay here again.
Guest favourite

Boat in Key West
4.98 out of 5 average rating, 42 reviewsWaterfront & Heated Pool - Awai's Floating Villa
ChelseaRating, 5 stars1 week ago
We stayed from Sunday to Friday and had an incredible time! The location was perfect—just a short drive to all the excitement of Key West, yet tucked away enough to feel peaceful and relaxing. The houseboat was spotless, cozy, and a perfect fit for our family of four. It had everything we needed for a comfortable stay. The resort itself was stunning, and the pool was the perfect way to unwind after a full day of exploring. The neighbors were so friendly, and the entire community had such a welcoming vibe. We would absolutely recommend this spot to anyone looking for a unique and relaxing getaway—and we’re already planning our next visit!

Apartment in Key West
4.86 out of 5 average rating, 29 reviewsApartment at Safe Harbor Marina
DrewRating, 5 stars1 day ago
This is our second time staying at this location and it honestly couldn’t be any better. The people around the marina are very friendly and inviting and the host is very responsive. We look to return soon.

Houseboat in Key West
4.74 out of 5 average rating, 190 reviewsDeluxe Bungalow
BradleyRating, 5 stars3 days ago
Aqua lodges were exactly as described and just what we needed. The value was great and we had a blast staying there. Marina restaurant was really good too.

Boat in Key West
5 out of 5 average rating, 4 reviewsLuxurious 40' Sailing Yacht!
ChristianRating, 5 stars1 day ago
We spent four amazing days aboard the Shelly Kay with Blue Ocean Yacht Charters, and it was truly an unforgettable experience. From the moment we arrived, Cassey made sure we felt welcome and taken care of. She was incredibly attentive, quick to help with any questions or small issues, and always available when we needed her. The boat itself was in top shape—immaculate, well-maintained, and surprisingly spacious. Our quarters were very comfortable and had everything we needed to relax and enjoy the trip. It felt like our own private floating resort! Our excursion was the highlight of the stay—stunning views, smooth sailing, and such a peaceful way to explore the beauty of Key West. We couldn’t have asked for a better experience. If you’re looking for a unique and luxurious way to enjoy the Keys, this is it. We’ll definitely be back!
Superhost

Houseboat in Stock Island
5 out of 5 average rating, 4 reviewsGreat Ocean Views! No regrets
Victor And TinaRating, 5 stars1 month ago
First time staying on a houseboat and it surely was a great experience! Beautiful views and comfy cozy space! Hosts were very friendly and welcoming and available with any questions we had. Thanks for a lovely experience!
Guest favourite

Boat in Key West
5 out of 5 average rating, 10 reviewsYacht Just Chillin': Anchored Out on the Ocean!
JacobRating, 5 stars1 month ago
My Wife and I truly enjoyed our stay. Capt. Kevin was a super nice guy and was willing to go the extra mile to make sure we enjoyed our stay. We enjoyed the privacy of our trip, and be able to “Just Chilling” after 3 days in the heart of Key West. Great Stay!!
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