Cottage in Upper Matecumbe Key, FL
2 guests · 1 bedroom · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this cottage rental
1940s Old Keys Fishing Cottage with dockage available. Large Waterfront property and walking distance to world famous Lorelei Cabana Bar & Restaurant as well as local breweries too ! This 1940s original Keys Fishing Cottage is not fancy, as the ad's photos show, but in great location and has everything you need for a great Islamorada getaway. We can arrange custom days of stay if you are booking a sunset/sandbar/fishing charter with our family. Enjoy the peace and privacy of the large, natural waters edge property with the convenience of being minutes away from some of the best dining and outdoor activities in the Florida Keys. Dockage is available on site for additional charge with free trailer storage. Relax in our 1940's "Old Florida Keys" style cottage which is updated while still maintaining its original look and feel ~ Original open beam ceilings and hard wood floors. Wi-Fi . Central air. King size bed in bedroom. There is one bath with original 1940s tile on walls, laundry area with full size washer and dryer. There is a second room that offers a desk for remote work and sitting area as well. We want you to enjoy your experience in the beautiful Florida Keys !! We are lifetime residents and our children born and raised here as well. This property is located conveniently within walking distance or at most ,less than half a mile to most Islamorada restaurants and local breweries. Kayak rentals and paddleboard rental is available for delivery to property. Great area for kayaking and paddle boarding. Launch right from water's edge of property. Please contact me prior to booking with any questions as I always want to make sure that the cottage is a good fit for prospective renters. Dockage is available at property for up to 35' boat for a fee of $50 per day with free trailer parking on premise payable upon arrival. No children please as the property is not fenced along the extensive water frontage and is not suitable. Thanks for checking out our listing :) If you book you will have a great time! *** Dockage Fee of $50 per day payable upon arrival and is NOT included in VRBO reservation fees and can be discounted dependent on length of your stay. You will have a fun time!! One Pet under 20 lbs welcome.. PLEASE ADD TO YOUR RESERVATION WHEN BOOKING. Thanks so much for liking our place ! :)
Amenities at WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei
Non-smoking
Pets allowed
Map of Upper Matecumbe Key, FL
Ratings and reviews
10 / 10Outstanding·Jun 2026
Everything exceeded our expectations. It was a perfect location from which to experience and explore the Florida Keys. The host, Jackie, was very accommodating, and one could not ask for more in terms of communication. The best compliment I can provide is that I dont want to say too much because I want the location to remain a "secret gem." Thanks again to Jackie for making our stay in Islamorada relaxing and memorable. Let's see, a perfect place to watch the sunset from your own dock: dolphins, manatees, sharks, parrot fish, mangrove snappers, iguanas, and peace and quiet.
10 / 10Outstanding·Jun 2026
Just finished up a wonderful week at the Cottage. Very clean and supplied with everything we needed. Large lot overlooking the bay and far enough from the road to not hear traffic. Enjoyed sitting on the deck in the evening watching the boats and listening to the band at Lorelei’s. Jackie was a great host and checked in to make sure all was well. Would love to return.
10 / 10Outstanding·May 2026
Jackie is an excellent host and gave us great insight on things to do in the area. Her home was perfect and conveniently located. We have no complaints everything was great.
10 / 10Outstanding·Apr 2026
This beautiful hideaway was an absolute dream! The welcoming aqua pineapples and fish at the end of the driveway, gorgeous tropical artist murals, and well kept yard and docks with beautiful water views made us feel like locals throughout our 2 week stay on Islamorada. Plus, it’s a short 3 minute walk to the Lorelei so we had live music and island cocktails almost every night. We had visits from a manatee, long-legged shore birds, iguanas and parrot fish! This cozy keys cottage has everything we needed for a care free stay. The host thought of absolutely everything from kitchen and bath necessities, to beach chairs, towels and coolers. But it is also so close to Publix for food, and a short drive to all the best waterfront restaurants. Also, there’s plenty of closet space for a longer stay. We loved every minute!
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Top rated by guests
9.9Outstanding
(141 Ratings)
"Everything exceeded our expectations. It was a perfect location from which to experience and explore the Florida Keys. The host, Jackie, was very accommodating, and one could not ask for more in term..."
Mark S.Don't miss out! Price and availability may change
