
Cottage vacation rentals in Key West
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Top-rated cottage rentals in Key West
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Popular amenities for Key West cottage rentals
Cottage rentals with a hot tub

OCEANIA... water front cottage retreat ~
Place was great. We loved the kayaks and Bikes that were there. Very clean and spacious. Beautiful view being on the canal. my negative I would say, which has nothing to do with the host, We were aware of the $125 resort fee, And our fee was increased to $145 cause my son’s large pickup. Curious as to what that fee actually pays for. We would definitely stay again.

ATLANTIS...Ocean Front Cottage Retreat!
We had an amazing 6-night stay at this waterfront Airbnb! The location is perfect—right on the water with gorgeous sunrise views. We used the provided kayaks every day, and my husband loved fishing off the deck while I relaxed in the sun. The house is super cute, clean, and beachy. The bed was very comfortable, and the kitchen was well-stocked with basics like spices and oil, making it easy to cook most of our meals. We also appreciated the strong, hot shower and provided toiletries. Extras like beach towels, umbrellas, fishing gear, and a washer/dryer made our stay even better. The area is peaceful, clean, and friendly—plus, Key West is just a short drive away. We’d definitely stay here again!

Tidewater Views at Venture Out
Great location, and a very practical and cute little house. The neighbor who resides on the ocean side was wonderful and inviting, which made the stay so much better. Well stocked kitchen. Lots of clean towels and name brand starter essentials. The down side, there was a bag of (assumed??) dirty bedding left by the door, which I contacted our concierge about when we arrived, and it went ignored until I brought it up at check out again. It worked out fine though, my kids brought their own blankets and used them instead. Everything else was great though!

Cozy, Perfect Conch Cottage! - VO315
Loved our stay! Clean place, great location and the community at VO is so nice. Great place to stay. Clean and cozy spot. Had everything we needed. Would definitely stay here again!

NAUTILUS...ocean front cottage retreat ~
Manuel was so kind and responsive! This place was sooo cute and perfect to stay in! The community felt super safe with the constant security, and he had so many amenities for us such as kayaks, fishing poles, bikes, kitchen supplies, hair dryer, etc. We had a slight issue with the wifi and he accommodated us to an extra day! It was soo sweet of him to do that and it made our stay extra fun:) Overall, I recommend 100% for anyone to stay here! It’s awesome. The pool and hot tub are so nice as well!

2BR dog-friendly water view stay, resort amenities
Perfect location for boaters and fishermen. Clean and mostly quiet canal with minimal low wake zone. House had all basics and very comfortable for my husband and I. Loved having the park nearby to take our dog, would recommend!

Conch Cabana in Paradise 23 miles outside Key West
Eliane was very easy to communicate with before and during our stay. She suggested some great things to do too! The place was clean and had everything we needed and more during our stay. I will absolutely stay here again!
Pet-friendly cottage rentals

Colony Sunset- Bright and airy cottage
The location was great. We parked our car and walked to everything. The condo was very nice and we loved the pool!

The Southern Cross
Place was just as advertised and pictured. Close to everything on Duval St. The pool is beautiful with lots of vegetation and wild life near it. Only thing to be aware of is that second bedroom upstairs would be a challenge for a tall person. Overall a great stay and I would definitely recommend and stay there again.

Hidden Oasis @ the Colony ~ Great location
Great place for 2 people for a week. Very peaceful and quiet. Parking was easy and there was a park within walking distance for pets which was great. The cottage was very clean and the grounds were well maintained. Would stay again.

Floating 2 BD, 1 BATH Private Villa Pirates Lair
We are definitely planning on coming back to stay. We only spent 2 nights here and I’m disappointed we booked another spot in the lower keys for the rest of our trip. The guys at the front desk were very friendly and helpful! We grabbed some local shrimp and bbq’d on the grill. Totally a comfortable, peaceful, and relaxing place to stay, but very close to everything

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
We loved staying here for the two nights we were on the Keys. The patio outside was great for looking at the stars or sipping coffee and watching manatees. We would definitely return!

Osprey @ Colony
Perfect place for two. Awesome location, within walking distance of Duval but far enough away that it’s nice and quiet at night. Beautiful little pool. Will 100% stay here again next visit to Key West

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Toni was very nice. She went out of her way to make sure we were satisfied with everything. The bed was comfortable and we got a great night's sleep there on the water. Watching the fish jump and pelicans dive as we sat on the front deck was very relaxing.

Prime Location 1B/1B Home
The resort itself is great with plenty of amenities and a perfect area to watch sunsets. The boat ramp is small and not very wide so if you’re bringing a boat be prepared to launch elsewhere and then parking your boat in a slip. It is at the top of Marathon and all the activities and restaurants are at the bottom part of the island, which is 10 miles away. Our cottage was roomy but in need of a coffee table or an ottoman and more side tables. The bed was not super hard and not super soft. There is no dishwasher so if you don’t want to do dishes bring paper plates, cups and plastic wear with you. I would consider staying here again, however, I would be sure to bring cleaning supplies with me as our cottage was dirty. There was dog hair all over the floor, the side table and trash left in the bathroom shower on top of the shampoo dispenser. Unless you are shorter than five feet you also won’t fit under the shower head so washing hair is challenging. Go to the comfort station instead.
Cottage rentals with a pool

Ann Street Tranquility
This charming unit exceeded our expectations and was wonderfully walkable yet totally private.

Ann Street Cottage
Comfortable cottage for 2 adults. Cooked dinner in a few nights, breakfast as well. Clean rooms, kitchen, bathrooms & bedding. Took a day to figure out where laundry was, but once we did more snooping, we found it across the small deck area. Only complaint/attention to maintenance: the decking off the living rm/bedroom is rotted. Extremely soft and about to break thru walking across it. Someone's likely to get hurt if the boards give way. Also the patio table on the deck should be replaced with something a little sturdier. It's shaky and legs are wobbling on the table. Our stay was very comfy and enjoyable. Easy walk to activities/bars/restaurants, yet tucked away enough that it was mostly quiet & definitely private our entire stay.

Colony Poolside: A charming bungalow near Duval
GREAT location. Our poolside location was fantastic and the staff were very helpful. My only complaint would be the bed. Rather thin mattress and the frame felt a little on the cheap side. This is the only bad thing I can say about our stay. Highly recommend

Stay at Hidden Treasure for a relaxing vacation!
We loved everything about the location and the accommodations. Beds were extremely comfortable. It was my daughter and her friend first time in KW and they loved it too. I would rent this place again as I have stayed in other areas of KW before and while they were good too, I just liked the vibe of this area. Thank you for the hospitality.

Pete's West Cottage steps from Duval
One of my favorite Airbnb’s and I’ve been to at least 20. Nicely decorated with comfortable furnishings and artwork. Kitchen well equipped and plenty of paper goods. Convenient to restaurants, beaches and shopping but not in the noisy bar area. The main bedroom was super quiet and the bed was comfortable. The pool is shared with just two units and never saw the other guests - so essentially a private landscaped pool/patio area with plenty of lounge chairs. Would love to return!

Pete's East Cottage: Cypress east cottage steps
We had a great stay. The pool was perfect in the heat of the afternoons, and so many great restaurants and sites to see within walking distance.

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
What a fantastic place to stay in Marathon! LeeAnn really makes sure you feel right at home. Forgot a toothbrush? Didn't pack or want to buy shampoo? No problem, it's there! The pool is amazing, house is spotless, and the Key Colony Beach community is the best. It is quiet and relaxing while also being in the heart of everything to do in the Florida Keys. LeeAnn is so nice and responsive, she got back to us quickly with any questions that we had. Overall, this was one of the nicest places that my family and I have ever stayed on a vacation. 10/10 would recommend to anyone!

Colony Calypso - A quaint 1 Bedroom Cottage
Nice little space for 2. Spacious rooms, great location. Privacy, quiet street Easy to walk or bike to many restaurants, museums, shops Nice little pool, there are beach towels available to use We would definitely recommend and stay again if in the area b
Quick stats about cottage rentals in Key West
Total rentals
40 properties
Nightly prices starting at
R1,442 ZAR before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
20 properties have a pool
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