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
4.86 out of 5 average rating, 66 reviews

Turtle Cove Views at Venture Out

CooganRating, 5 stars2 weeks 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 stars5 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
4.7 out of 5 average rating, 138 reviews

Calypso Cottage

CoriRating, 5 stars2 months ago
Exactly as described and good location. About 30-45 minutes from Key West activities and a lot of stuff to do at the house - we loved the kayaks, bikes, and pool.
Cottage in Cudjoe Key
4.9 out of 5 average rating, 151 reviews

ATLANTIS...Ocean Front Cottage Retreat!

MichelleRating, 5 stars1 month ago
This was the first family vacation we have had in several years, and we were celebrating our son's graduation from college and new career. We had such a relaxing time and had so much fun. We would recommend the Atlantis Cottage to any traveler's going to the keys.
Cottage in Cudjoe Key
4.88 out of 5 average rating, 58 reviews

NAUTILUS...ocean front cottage retreat ~

KristinaRating, 5 stars3 months ago
Our stay was absolutely great, exceeded all expectations. The house was clean, cozy, with gorgeous views, and exactly as described in the listing. The host was incredibly welcoming and responsive, making sure we had everything needed. Will definitely stay again if in the area!
Cottage in Key Colony Beach
4.63 out of 5 average rating, 8 reviews

2BR dog-friendly water view stay, resort amenities

StephanieRating, 5 stars3 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!
Superhost
Cottage in Cudjoe Key
New place to stay

Ocean Breeze at Venture Out 537

Pet-friendly cottage rentals

Guest favourite
Cottage in Key Largo
4.96 out of 5 average rating, 75 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

AprilRating, 5 stars5 days ago
Very relaxing and beautiful by the water's edge! Nice people, lots to do, swim in heated pool, ride bicycles, take walks, fish, kayak, sit and relax! Nice facilities for visitors, laundromat, front desk very helpful and open on the weekends! Next door is shopping center with Publix groceries, liquor store, and lots more. Betty was exceptional with info on all Key Largo eats and fun! This cottage by the water was perfect size and had everything we needed to relax and enjoy some much needed time away!
Superhost
Cottage in Key West
4.83 out of 5 average rating, 6 reviews

The Southern Cross

AllisonRating, 5 stars4 months ago
We enjoyed our stay. Very close to Duval and southernmost point. Plenty of space for 2 couples. Enjoyed having a kitchen. Host was responsive. Had issue with front gate but it was promptly taken care of. Wish upstairs room had small set of drawers and full length mirror somewhere in house. Would rent again!
Cottage in Key Largo
4.7 out of 5 average rating, 10 reviews

1 Bedroom Home in Key Largo

NerysRating, 5 stars2 months ago
Beautiful cottage, everything you need for a home from home. Great base to explore the keys. Thanks for a wnderful stay
Superhost
Cottage in Key West
4.84 out of 5 average rating, 80 reviews

Hidden Oasis @ the Colony ~ Great location

GeorgeRating, 5 stars3 months ago
Great stay and perfect location to all I wanted to do and see. Very let friendly as well. I will be back
Superhost
Cottage in Key Largo
4.75 out of 5 average rating, 12 reviews

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

JesslynRating, 5 stars30 months ago
Overall we enjoyed our time here. It can be hard to find from the road but has a rustic charm to it. Enjoyed kayaking and time in the tiki hut by the water.
Guest favourite
Cottage in Islamorada
4.96 out of 5 average rating, 25 reviews

Floating 2 BD, 1 BATH Private Villa Pirates Lair

HamiltonRating, 5 stars1 month ago
First time staying in a house boat. Can't wait to do it again! The place is great for couples or small families. The experience was great--morning coffee wathing the fish jump and local manatees swim by--then off to the beach or fishing. Return to an evning out on the water again. The harbor is just far enough from the highway to minimize the car noise, which was an added bonus. Even rented a boat for the day to explore the Keys.
Superhost
Cottage in Islamorada
4.75 out of 5 average rating, 174 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

PaigeRating, 5 stars2 months ago
My husband and I had a great time here! We were amazed at all the fish and manatees we saw! My husband was in heaven getting to fish off the balcony and a manatee swam right up to us and went under the house! Such a cool experience! All the staff we interacted with were super friendly and great! Highly recommend!
Superhost
Cottage in Key West
4.66 out of 5 average rating, 29 reviews

Osprey @ Colony

JenniferRating, 5 stars3 months ago
Our stay at The Osprey was incredible. The cottage looked just like the pics, light and airy in classic Key West style. The heated pool in the middle of courtyard area was such a nice amenity, and the foliage overhead was just breathtaking. Our car never left the parking spot and we were able to either walk or take the trolley everywhere we wanted to go on the island. We hope to stay here again and again!

Private cottage rentals

Superhost
Cottage in Key West
4.75 out of 5 average rating, 8 reviews

Ann Street Cottage

EricRating, 5 stars1 month ago
My wife and I had a fantastic stay. it's so close to Duvall and all the restaurants and bars in the area. plus the pool was very private, crystal clear, and shared amongst only a couple of cottages. The gardens in the area were awesome as well . We loved the combination of proximity to downtown and the privacy stay!
Guest favourite
Cottage in Islamorada
4.96 out of 5 average rating, 73 reviews

Islamorada bungalow 2 bed & pool

ChristieRating, 5 stars1 week ago
Yasmin and Joe were very responsive and friendly in all of their communications. The bungalow was perfect for my daughter, cousin and I. The decorations and amenities were very well done and made you feel very welcome. Having the pool right next door was wonderful. The location is convenient to restaurants, boating activities and shopping. It is a bit close to A1A so there is road noise, but the hosts provide noise makers in the bedrooms which make it all go away. Overall a great place to have a vacation!
Superhost
Cottage in Key West
4.71 out of 5 average rating, 14 reviews

Colony Poolside: A charming bungalow near Duval

EricaRating, 5 stars15 months ago
We loved our time at Colony Poolside! We spent a long weekend at Colony Poolside (it was our second stay in this location). The rental was exactly like the pictures, clean and comfortable. The kitchen was well stocked, and there were even beach towels, sunblock and a workout mat. The pool was clean and quiet. Short walk to Duval and lots of great restaurants. We would highly recommend!
Cottage in Islamorada
5 out of 5 average rating, 13 reviews

Anglers Reef Islamorada

SigridRating, 5 stars5 months ago
We loved our stay at this community. It’s very cozy and clean. The surroundings are well kept! Felt safe with the gate closed at all times. The swimming pool area is pretty much close to any unit so it’s easy to walk over there. The unit itself was very comfortable. The kitchen is well equipped with plenty of pots and pans for cooking. We truly enjoyed our stay!
Cottage in Key Colony Beach
5 out of 5 average rating, 10 reviews

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

DawnRating, 5 stars11 months ago
Leeann’s place exceeded our expectations! She was incredibly responsive to any concerns or inquiries we had throughout our stay. The added perk of access to Glunz Beach Resort with its beach, pool, and gym made our experience even more delightful. The house was equipped with everything we needed for a comfortable stay. Thank you, Leeann!
Superhost
Cottage in Key West
4.77 out of 5 average rating, 13 reviews

Colony Calypso - A quaint 1 Bedroom Cottage

SalarRating, 5 stars7 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, 77 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

JoieRating, 5 stars2 weeks ago
We had a great time at Shady Palms. Quiet neighborhood, pretty shared pool that was well maintained with plenty of seating and a couple of umbrellas. Bike path right access close by. We have two teenage sons and it was a tight squeeze in the cottage but we made it work as we were out and about fishing and exploring every day. Highlight was Bahia Honda State Park which is an hour south. This rental has no dishwasher, something I missed looking for in the listing so worth a mention. Overall highly recommend!
Guest favourite
Cottage in Key Largo
4.9 out of 5 average rating, 61 reviews

Kampground Retreat w/ Kayaks,Heated Pool & More

FrancinaRating, 5 stars3 weeks ago
We were there 4 nights and wished we could have stayed longer. The house is a park model, very spacious. Lots of closet and cabinet space. Awesome, big refrigerator. The deck is really nice with lots of places to sit. The campground is right on the water, has 2 small beaches. The house comes with beach chairs, umbrella and a kayak. All in all a very pleasant stay in Key Largo.

Quick stats about cottage rentals in Key West

  • Total rentals

    40 properties

  • Nightly prices starting at

    $143 AUD before taxes and fees

  • Total number of reviews

    1.5K 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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  4. Monroe County
  5. Key West
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