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
4.81 out of 5 average rating, 99 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.
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 stars2 weeks 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

Superhost
Cottage in Key West
4.8 out of 5 average rating, 20 reviews

Colony Sunset- Bright and airy cottage

PollyRating, 5 stars3 weeks ago
The location was great. We parked our car and walked to everything. The condo was very nice and we loved the pool!
Cottage in Key Largo
4.75 out of 5 average rating, 16 reviews

1 Bedroom Home in Key Largo

HollyRating, 5 stars1 week ago
This was such a fun stay! The little beach cottages were so cute. The bedroom is rather tight and the loft is designed for children size guests, but we didn't mind. The kitchen had everything we needed, the dock and beach area were where we spent most of our time outside of wedding festivities, the grill and firepits were a nice touch too. The guy working the whole time we were there was great, he was great with communication and super friendly. Hard worker! I will say we did not get the house from the post- but only the picture of the outside. Which was totally fine, the inside was exactly the same. Another guest in our party had the same experience but didn't get a loft- but if you are like them and didn't need a loft those cabins were actually nicer. I read other reviews stating they didn't get the cabin they requested, but it seemed like there were only a few different variations of exactly the same model with different external design. I'd do it all again!
Superhost
Cottage in Key West
4.83 out of 5 average rating, 84 reviews

Hidden Oasis @ the Colony ~ Great location

EricRating, 5 stars1 week 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.
Guest favourite
Cottage in Islamorada
4.84 out of 5 average rating, 32 reviews

Floating 2 BD, 1 BATH Private Villa Pirates Lair

SondraRating, 5 stars1 month ago
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
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
4.62 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!
Cottage in Marathon
4.78 out of 5 average rating, 32 reviews

Prime Location 1B/1B Home

AngelaRating, 5 stars1 week ago
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.

Private cottage rentals

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!
Superhost
Cottage in Key West
4.78 out of 5 average rating, 9 reviews

Ann Street Cottage

PaigeRating, 5 stars2 months ago
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.
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!
Superhost
Cottage in Key West
4.83 out of 5 average rating, 23 reviews

Pete's East Cottage: Cypress east cottage steps

AmberRating, 5 stars1 month ago
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.
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

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

MatthewRating, 5 stars2 months 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 West
4.73 out of 5 average rating, 15 reviews

Colony Calypso - A quaint 1 Bedroom Cottage

DianeRating, 5 stars1 month ago
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
Cottage in Marathon
4.67 out of 5 average rating, 6 reviews

Waterfront 1B/1B Tiny Home

MatthewRating, 5 stars2 months ago
We had a great stay in their tiny house. The neighbor’s were all nice and friendly. The locals that live inside the campground are absolutely wonderful very nice and full of local information where to go and what to do.
Cottage in Marathon
4.66 out of 5 average rating, 38 reviews

Cute 1B/1B Lofted Cottage

JenniferRating, 5 stars1 week 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!

Quick stats about cottage rentals in Key West

  • Total rentals

    40 properties

  • Nightly prices starting at

    $123 AUD 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

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