Cottage holiday rentals in Key West

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Popular amenities for Key West cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Cudjoe Key
4.87 out of 5 average rating, 67 reviews

Turtle Cove Views at Venture Out

CooganRating, 5 stars1 month ago
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.
Cottage in Cudjoe Key
4.81 out of 5 average rating, 95 reviews

OCEANIA... water front cottage retreat ~

RachelRating, 5 stars7 months ago
If we could rate this 6+ stars out of 5, we would! Manuel was super easy to reach, he provided simple and clear instructions, the guards at the gate were easy to work with and available for 24/7 entry and check in.. the location is unbeatable for a boat owner! You dock right at your back door, clean your fish at the back door OR at the marina, immediate access to the Atlantic.. perfection. The home itself is extremely clean & beautiful. The kitchen and bathrooms were all stocked with anything you’d need as well as even the laundry room! We truly felt at home but twice as relaxed! Thanks Manuel!!
Cottage in Cudjoe Key
4.9 out of 5 average rating, 152 reviews

ATLANTIS...Ocean Front Cottage Retreat!

JeanRating, 5 stars1 month ago
Manuel's home was clean, bright, quiet, and peaceful with a million dollar view. It sits directly on big open water which we enjoyed from the nice open porch. We ate meals on the porch while relaxing and savoring the amazing view of the blue water and the two islands beyond. We never tired of the view. The whole neighborhood is quiet and clean, and there is a small beach and a pool. The check in/check out process was simple and Manuel was responsive with all communications. We enjoyed exploring Key West (about a 30-35 minute drive) and walking the old train/then road Old Seven Mile Bridge from Marathon Key to Pigeon Key. The Bridge is a beautiful 4 mile round trip walk to small Pigeon Key where we swam and participated in a guided walking tour and shark feeding. If you're looking for a peaceful, relaxing, home with an amazing view to get away from it all, Manuel's home is the answer! It was perfect for my husband and me.
Cottage in Cudjoe Key
4.88 out of 5 average rating, 59 reviews

NAUTILUS...ocean front cottage retreat ~

JessicaRating, 5 stars1 month ago
Super responsive host! Place was great if you’re looking for a relaxed vibe. Close enough to key west but much less crowded relaxing vacation. My kids loved the pool and ocean being so close.
Cottage in Key Colony Beach
4.55 out of 5 average rating, 11 reviews

2BR dog-friendly water view stay, resort amenities

StephanieRating, 5 stars5 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!

Pet-friendly cottage rentals

Guest favourite
Cottage in Islamorada
4.97 out of 5 average rating, 29 reviews

Floating 2 BD, 1 BATH Private Villa Pirates Lair

PaulRating, 5 stars2 weeks ago
The place was awesome! So perfect! They helped with getting our jetskis in the water and let us tie them up to the doc. We'll definitely be back. Thank you Toni and Jay!
Cottage in Islamorada
4.75 out of 5 average rating, 175 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

JaceyRating, 5 stars3 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 Marathon
4.67 out of 5 average rating, 6 reviews

Waterfront 1B/1B Tiny Home

MatthewRating, 5 stars1 month 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
4.67 out of 5 average rating, 33 reviews

Cute 1B/1B Lofted Cottage

AmyRating, 5 stars3 weeks ago
What a beautiful, peaceful spot to stay! Family friendly and exceeded expectations. Great location to explore all of the Keys but always a nice, private and quiet place to come back to. Would absolutely stay here again!
Cottage in Marathon
4.75 out of 5 average rating, 12 reviews

Waterview 1B/1B Tiny Home

RuthRating, 5 stars4 weeks ago
We absolutely loved it here and would've happily stayed for weeks! The tiny house was cute, clean and comfy with everything we needed. The location was perfect, would give it 110%. Beautiful sea view, amazing sunsets and the children enjoyed the games in the clubhouse and the pool. There are also lots of things to do nearby. Probably the best place we've ever stayed.
Cottage in Islamorada
4.82 out of 5 average rating, 155 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

T LRating, 5 stars2 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, 116 reviews

Tropical Cottages - Cottage # 10

LoriRating, 5 stars1 month ago
The Airbnb had a great location. My husband enjoyed the local fishing, which was a block away. The Airbnb was clean and very comfortable. We also enjoyed the taco truck and Tiki bar located on the premises. The most important thing was that we could bring our dog Chloe and felt comfortable and safe. We will come back again to the cottage.
Cottage in Marathon
4.73 out of 5 average rating, 26 reviews

Prime Location 1B/1B Home

AbbyRating, 5 stars3 weeks ago
We thoroughly enjoyed our stay! The cottage was very clean and comfortable with plenty of space for three adults. We especially loved the pool and proximity to the ocean - the views were stunning! Just a quick note about parking: the house rules state that parking for one vehicle is included with each reservation, but we were able to park both of our cars with no issue.

Private cottage rentals

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

Ann Street Tranquility

LisaRating, 5 stars5 months ago
This charming unit exceeded our expectations and was wonderfully walkable yet totally private.
Superhost
Cottage in Key West
4.77 out of 5 average rating, 13 reviews

Colony Calypso - A quaint 1 Bedroom Cottage

SalarRating, 5 stars9 months ago
Our stay was fantastic, the host was amazing and incredibly responsive. No issues at all, however, the Vacasa utility workers have a habit of entering the back patio areas unannounced. I think just a simple initial knock at the door, and a subsequent announcement of their entry would be satisfactory. This takes nothing away from the property or the hosts themselves, I believe Vacasa is a vendor. The stay itself was absolutely amazing, think rainforest escape to a beautiful place. The vibe was immaculate and I loved the pool. Stay here if you can, it is so worth it.
Cottage in Islamorada
4.78 out of 5 average rating, 80 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

JustinRating, 5 stars4 weeks ago
The place and location were perfect. We were looking for a no frills type of place so my kids would have to spend time without devices and just be outside. This little place is exactly what we needed, it’s just big enough to sleep, eat a quick breakfast and head out for the day on the keys. The pool area is really nice and everything was great. It does not come with any extras..like beach bike, beach chairs or extra beach towels so you may want to bring your own. We left a few behind for the next family to enjoy. Over all this was a very clean and nice place to stay in a good neighborhood located to almost everything.
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

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

MatthewRating, 5 stars2 weeks 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!

Quick stats about cottage rentals in Key West

  • Total rentals

    40 properties

  • Nightly prices starting at

    $124 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