
Cottage vacation rentals in Key West
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Top-rated cottage rentals in Key West
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Popular amenities for Key West cottage rentals
Cottage rentals with a pool

Ann Street Cottage
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.

Islamorada bungalow 2 bed & pool
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

The Southern Cross
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!

Coral Reef Cottage
Great place! Nice and quite complex. Highly recommended

Colony Poolside: A charming bungalow near Duval
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!

Pete's West Cottage steps from Duval
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!

Kampground Paradise w/Kayaks, Heated Pool & Marina
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 :)

Pete's East Cottage: Cypress east cottage steps
Great location! Pool was great! We enjoyed our stay!
Cottage rentals with a hot tub

Turtle Cove Views at Venture Out
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.

OCEANIA... water front cottage retreat ~
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!!

Calypso Cottage
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

ATLANTIS...Ocean Front Cottage Retreat!
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.

Darling of Duval at Old Town
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.

NAUTILUS...ocean front cottage retreat ~
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.

2BR dog-friendly water view stay, resort amenities
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

Colony Sunset- Bright and airy cottage
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!

2 bedroom & 25' Boat Dock Waterfront Atlantic Side
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.

Stay at Hidden Treasure for a relaxing vacation!
Comfortable accommodations, located in a quiet neighborhood. Pool was nice and we enjoyed the private courtyard. Beds were very comfortable as well!

Hidden Oasis @ the Colony ~ Great location
Great stay and perfect location to all I wanted to do and see. Very let friendly as well. I will be back

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

Tropical Cottages - Cottage # 10
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.

Prime Location 1B/1B Home
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.

Water View House in Key Largo
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
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