Cottage holiday rentals in Key West

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Popular amenities for Key West cottage rentals

Cottage rentals with a hot tub

Cottage in Cudjoe Key
4.82 out of 5 average rating, 98 reviews

OCEANIA... water front cottage retreat ~

DeniseRating, 5 stars1 month ago
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.
Superhost
Cottage in Cudjoe Key
4.63 out of 5 average rating, 112 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

Elizabeth CarmenRating, 5 stars3 months ago
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!!
Cottage in Cudjoe Key
4.9 out of 5 average rating, 154 reviews

ATLANTIS...Ocean Front Cottage Retreat!

WendyRating, 5 stars1 month ago
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!
Superhost
Cottage in Cudjoe Key
4.86 out of 5 average rating, 37 reviews

Tidewater Views at Venture Out

KatieRating, 5 stars1 month ago
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!
Cottage in Cudjoe Key

Cozy, Perfect Conch Cottage! - VO315

StephanieRating, 5 stars2 months ago
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!
Cottage in Cudjoe Key
4.85 out of 5 average rating, 61 reviews

NAUTILUS...ocean front cottage retreat ~

AngelaRating, 5 stars1 month ago
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!
Cottage in Key Colony Beach
4.55 out of 5 average rating, 11 reviews

2BR dog-friendly water view stay, resort amenities

StephanieRating, 5 stars6 months ago
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!
Guest favourite
Cottage in Cudjoe Key
4.9 out of 5 average rating, 29 reviews

Conch Cabana in Paradise 23 miles outside Key West

MelodyRating, 5 stars1 week ago
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

Guest favourite
Cottage in Key Largo
4.93 out of 5 average rating, 82 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

SaraRating, 5 stars1 week ago
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!
Guest favourite
Cottage in Key Largo
4.92 out of 5 average rating, 79 reviews

Spacious cottage - the Calusa campground-keylargo

CraigRating, 5 stars1 month ago
Very nice indoor/outdoor living. Convenient outdoor kitchen and fridge allowed us to cook, store, and eat all meals on the patio.
Superhost
Cottage in Key West
4.83 out of 5 average rating, 84 reviews

Hidden Oasis @ the Colony ~ Great location

EricRating, 5 stars5 days ago
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.
Superhost
Cottage in Key Largo
4.77 out of 5 average rating, 13 reviews

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

KlaraRating, 5 stars2 months ago
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!
Cottage in Islamorada
4.75 out of 5 average rating, 175 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

JaceyRating, 5 stars4 months ago
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!
Cottage in Islamorada
4.79 out of 5 average rating, 156 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

T LRating, 5 stars4 months ago
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.
Cottage in Marathon
4.66 out of 5 average rating, 38 reviews

Cute 1B/1B Lofted Cottage

JenniferRating, 5 stars6 days ago
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!
Cottage in Marathon
4.62 out of 5 average rating, 117 reviews

Tropical Cottages - Cottage # 10

ChrisRating, 5 stars2 months ago
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

Superhost
Cottage in Key West
4.64 out of 5 average rating, 11 reviews

Ann Street Tranquility

LisaRating, 5 stars6 months ago
This charming unit exceeded our expectations and was wonderfully walkable yet totally private.
Superhost
Cottage in Key Largo
4.89 out of 5 average rating, 19 reviews

Cottage w/ Full Kitchen FREE sailboats and kayaks

MartinRating, 5 stars28 months ago
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!
Cottage in Key Largo
3.5 out of 5 average rating, 4 reviews

Coral Reef Cottage

PrimeRating, 5 stars45 months ago
Great place! Nice and quite complex. Highly recommended
Guest favourite
Cottage in Key West
4.75 out of 5 average rating, 16 reviews

Colony Poolside: A charming bungalow near Duval

BrianRating, 5 stars4 weeks ago
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
Superhost
Cottage in Marathon
4.96 out of 5 average rating, 26 reviews

Waterfront cottage w/ MotherInLaw suite&boat slip

RachelRating, 5 stars10 months ago
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!
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

MatthewRating, 5 stars1 month ago
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!
Guest favourite
Cottage in Key Largo
4.92 out of 5 average rating, 73 reviews

Kampground Escape /w Kayaks, Heated Pool And More

MichaelRating, 5 stars1 week ago
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.
Cottage in Islamorada
4.78 out of 5 average rating, 82 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

DonnaRating, 5 stars2 weeks ago
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

Destinations to explore

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  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Cottage rentals