Cottage vacation rentals in Key West

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Popular amenities for Key West cottage rentals

Cottage rentals with a pool

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

Ann Street Cottage

PaigeRating, 5 stars1 month 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.
Guest favorite
Cottage in Islamorada
4.96 out of 5 average rating, 79 reviews

Islamorada bungalow 2 bed & pool

KatieRating, 5 stars4 days ago
Beautifully decorated bungalow with everything you need for a relaxing holiday. We stayed with our two boys who loved the pool next door and the fire pit in the back garden. Great base for exploring Islamorada. Recommend watching the sunset and enjoying some great food at Papa Joes. Lovely responsive host
Superhost
The outdoor deck provides a spacious area for dining and relaxation, framed by lush greenery. Two flags flutter gently in the breeze, while a mix of natural wood and beige gravel enhance the serene atmosphere of this tropical retreat.
Cottage in Key West
4.83 out of 5 average rating, 6 reviews

The Southern Cross

AllisonRating, 5 stars5 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!
A two-story yellow house with white trim features a welcoming front porch and wooden steps. Lush palm trees and a manicured garden surround the entrance, contributing to the inviting atmosphere. A gravel driveway leads to the house, with a serene view of the water visible in the background.
Cottage in Key Largo
3.5 out of 5 average rating, 4 reviews

Coral Reef Cottage

PrimeRating, 5 stars44 months ago
Great place! Nice and quite complex. Highly recommended
Superhost
A charming entrance features double French doors framed by lush greenery. The brick pathway leads to the entrance, with soft lighting from wall sconces accentuating the space. Latticework indicates nearby outdoor areas, while bike racks complete the inviting entry.
Cottage in Key West
4.71 out of 5 average rating, 14 reviews

Colony Poolside: A charming bungalow near Duval

EricaRating, 5 stars16 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!
Guest favorite
A kidney-shaped pool is surrounded by a white deck, featuring steps that lead into the water. Two lounge chairs are positioned beside the pool, and lush greenery creates a private atmosphere.
Cottage in Key West
5 out of 5 average rating, 30 reviews

Pete's West Cottage steps from Duval

AndrewRating, 5 stars3 weeks ago
What an excellent little spot! Could not have asked for a better location to Duval and some excellent food, drinks and excursions. The home was clean, cool and met our needs nicely. We did share the pool with another adjoining bungalow, and the people visiting were very friendly and gracious. We shared some pool time, drinks and laughs. La Grignote (which is directly in from of us on Duval) is NOT to be missed. Thanks for the memories!
Top guest favorite
A sandy beach area is shown, framed by dense greenery and clear water. Colorful kayaks and paddleboards are arranged on a rack nearby, with a spacious pool visible under a bright sky, surrounded by lounge chairs. A charming cottage showcases large windows, allowing natural light to fill the interior.
Cottage in Key Largo
5 out of 5 average rating, 5 reviews

Kampground Paradise w/Kayaks, Heated Pool & Marina

TylerRating, 5 stars1 day ago
What an amazing stay!! The campground was so peaceful and tucked away from everyday reality. This trip was a much needed escape from our everyday life! The cottage was very new and clean and came with all the amenity’s needed to enjoy all the local beaches. The host was great and responded immediately with any questions we had. We will for sure be back again :)
Superhost
Cottage in Key West
4.82 out of 5 average rating, 22 reviews

Pete's East Cottage: Cypress east cottage steps

SaraRating, 5 stars1 month ago
Great location! Pool was great! We enjoyed our stay!

Cottage rentals with a hot tub

Superhost
An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.
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.
A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.
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!!
Superhost
A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.
Cottage in Cudjoe Key
4.7 out of 5 average rating, 145 reviews

Calypso Cottage

CourtneyRating, 5 stars1 week ago
Place was exactly like described, super quaint and had a great homey cottage feel. Neighbors were all super friendly as well. We really enjoyed being able to sit outside on the canal and enjoy our breakfast/dinner as well as playing any games. Would highly recommend this place, not far from key west a matter of 35-45 min depending on traffic
An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.
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.
Superhost
The two-story cottage is framed by lush tropical vegetation, with prominent palm leaves. Illuminated doorways reveal a welcoming interior, while a balcony overlooks the entrance, suggesting a space for relaxation. The exterior features light-colored walls that harmonize with the natural surroundings.
Cottage in Key West
4.74 out of 5 average rating, 31 reviews

Darling of Duval at Old Town

JoeRating, 5 stars1 month ago
What a great place to stay for a Key West trip! Perfect location, lots to do, super short walk to Duval St. Very easy check in, and Last Key were easily available for questions.
An aerial view presents a light blue cottage alongside a canal, with white lounge chairs positioned on the deck. A kayak rests in the water, surrounded by lush palm trees and calm, clear waters reflecting a bright blue sky.
Cottage in Cudjoe Key
4.88 out of 5 average rating, 59 reviews

NAUTILUS...ocean front cottage retreat ~

JessicaRating, 5 stars2 weeks 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.
A bright living area features a comfortable gray sofa and an upholstered ottoman. Large sliding doors open to a water view, letting in natural light. A small dining table with patterned chairs is positioned near the window, complemented by a ceiling fan and modern decor.
Cottage in Key Colony Beach
4.56 out of 5 average rating, 9 reviews

2BR dog-friendly water view stay, resort amenities

StephanieRating, 5 stars4 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

Superhost
The living area features a gray sofa complemented by a colorful area rug. A flat-screen television is mounted on the wall. A small bar with seating connects to the kitchen area, adorned with bamboo window treatments, enhancing the bright and airy ambiance.
Cottage in Key West
4.79 out of 5 average rating, 19 reviews

Colony Sunset- Bright and airy cottage

MaureenRating, 5 stars12 months ago
What a great find! Everything we needed was there! Quick walk to everywhere: beach, Duval street fun, restaurants and grocery store. So glad we went with this air bnb and not the hotel we normally go to. Saved so much money. Loved the privacy!
Guest favorite
The tranquil canal is illuminated by soft lights reflecting off the crystal-clear waters. Lush palm trees line the banks, and tiki huts with ambient lighting add to the serene atmosphere. The scene captures a peaceful nighttime setting with boats moored along the dock.
Cottage in Key Largo
4.96 out of 5 average rating, 77 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

SethRating, 5 stars1 month ago
My family had a great stay! The location is awesome. We really enjoyed the outdoor space and all the amenities at the campground. Betty was a fantastic host.
Superhost
An outdoor seating area features a round table with four yellow chairs beneath a large umbrella. A gas grill is positioned nearby on a wooden deck surrounded by lush greenery and tropical plants. Large French doors lead into the cottage.
Cottage in Key West
4.71 out of 5 average rating, 89 reviews

Stay at Hidden Treasure for a relaxing vacation!

LisaRating, 5 stars1 month ago
Comfortable accommodations, located in a quiet neighborhood. Pool was nice and we enjoyed the private courtyard. Beds were very comfortable as well!
Superhost
A charming outdoor space is shown with a small circular table and two chairs set on a stone patio. Lush greenery surrounds the area, and wooden steps lead to the entrance of the cottage. A tree provides shade, enhancing the serene ambiance.
Cottage in Key West
4.84 out of 5 average rating, 80 reviews

Hidden Oasis @ the Colony ~ Great location

GeorgeRating, 5 stars4 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
The open layout features a spacious sleeping area with a king-size bed decorated in blue and white patterns. A cozy sitting area includes a large sofa, while a dining table is visible in the background, complemented by cheerful green walls and tropical-themed decor.
Cottage in Key Largo
4.77 out of 5 average rating, 13 reviews

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

KlaraRating, 5 stars1 month 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!
A charming cottage exterior features light blue siding and is accented by vibrant pink Adirondack chairs. Lush greenery surrounds the entrance, and flowering plants add color to the setting. A clear blue sky and tropical palm trees complete the welcoming atmosphere.
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.
A bright living area features a large flat-screen TV mounted beneath a stylish white cabinet. Natural light pours in through multiple windows, illuminating the modern gray sofa and round seating options. Air conditioning units are visible in the ceiling, providing comfort to the space.
Cottage in Marathon
4.72 out of 5 average rating, 25 reviews

Prime Location 1B/1B Home

AbbyRating, 5 stars2 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.
A sleeper sofa is displayed in a well-lit corner room, featuring large windows that allow natural light to fill the space. The sofa is laid out with a freshly made white bedspread, complemented by two soft pillows and a rolled gray blanket.
Cottage in Key Largo
4.67 out of 5 average rating, 12 reviews

Water View House in Key Largo

HannahRating, 5 stars6 days ago
This property was one of the best stays I’ve ever had with air bnb! Beautiful views from the windows of the air bnb, and the property is just steps away from the water. The beach area is small but was quiet, peaceful, and so relaxing. This property faces the sunset side of the keys, we watched the most beautiful sunsets over the water here. There was also some marine life in the water, we saw a manatee pass us just about 10 feet away! We really enjoyed using the kayaks, and it was helpful this air bnb had a full kitchen to stay in and eat for some meals. The tiny house itself was very clean. Good location with very short drives to restaurants and activities. We would definitely stay here again in the future!

Quick stats about cottage rentals in Key West

  • Total rentals

    40 properties

  • Nightly prices starting at

    $80 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