
Cottage holiday rentals in Key West
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Top-rated cottage rentals in Key West
Guests agree: These cottages are highly rated for location, cleanliness and more.
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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.

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Jason’s place was a great place to stay in the keys!! Jason is great at responding great location, clean house only the couch could use a cleaning. It would have been nice if there were trash bags, extra hand soap and extra toilet paper. Other then that it was perfect!!

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

2 bedroom & 25' Boat Dock Waterfront Atlantic Side
Betty is a wonderful host! She makes sure her guests feel at home. We've stay at her place multiple years and we always have a fantastic experience! It's a great place to do some relaxing, boating and fishing!

Spacious cottage - the Calusa campground-keylargo
Very nice indoor/outdoor living. Convenient outdoor kitchen and fridge allowed us to cook, store, and eat all meals on the patio.

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.

Cottage w/ Private Yard, Free Kayaks, Boats, Etc
We really enjoyed our stay with Key Lime sailing club! We especially appreciated the easy access to water activities and created life long memories kayaking in the beautiful surroundings. The hosts are kind, helpful and made our stay more memorable!

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!

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.

Cute 1B/1B Lofted Cottage
Great distance to everything in the Keys. We stayed for several days and was able to hit all the spots- snorkeling, Key West, national parks. Close to restaurants, fishing and much more. Manager and maintenance were very responsive to questions, within minutes. Would stay here again!

Tropical Cottages - Cottage # 10
Perfect getaway for a couple, very quaint cottages. Bonus is the taco food truck on property as well as the covered bar area. Would definitely stay again!
Private cottage rentals

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

Cottage w/ Full Kitchen FREE sailboats and kayaks
First time family trip to key largo, great having everything we needed in one place. Klsc staff was friendly and accommodating. Will be back again!

Coral Reef Cottage
Great place! Nice and quite complex. Highly recommended

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

Waterfront cottage w/ MotherInLaw suite&boat slip
We absolutely loved this charming cottage and Conch Key. Barry made sure we had everything we needed, and offered advice and insight into the surrounding area. The views from the dock and the character of the cottage made our trip everything we wanted it to be. We will definitely be back!

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!

Kampground Escape /w Kayaks, Heated Pool And More
This place is in a great location, near many restaurants, shopping (Publix and Burlington Coat Factory are 1/2 mile away), is very comfortable and easy to figure out. We enjoyed sitting outside and watching the world go by while relaxing on the couch and having a few drinks. Loved our little weekend away in paradise. Very much enjoyed snorkeling with Sundiver Snorkeling Tours, which is very close by.

Serene Cozy Cottage in Islamorada with Heated Pool
Great choice! Very close to everything, central. Pool was so nice & our own mostly. Cottage is modern clean & comfortable. Perfect for a girls trip!
Quick stats about cottage rentals in Key West
Total rentals
40 properties
Nightly prices starting at
$133 NZD 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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