WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei
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
Free cancellationFull refund if you change your mind
Great for petsBring all your friends and family, even the furry ones
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 $25 per day 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 payable upon arrival and not included in VRBO reservation fees and can be discounted dependent on length of your stay. You will have a fun time!!
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Map of Upper Matecumbe Key, FL
Ratings and reviews
10.0 / 10.0
This property is as described. It is secluded and in close vicinity to shopping, restaurants and bars. The dock is well maintained & situated in such a way to be protective from boat wakes in Morada Bay. The house is adorable and very comfortable. The house is stocked with enough supplies that we didn't have to go buy the necessities. There were coffee pods, shampoo & body wash and laundry soap, etc.
The host invited questions and conversation. We highly recommend and will rent again!!
10.0 / 10.0
Great communication with host. The location far exceeded
our expectations and was in the heart of it all. The canal was crystal clear and made a
perfect spot to spend winding down the day. I highly recommend this cozy house to anyone who wants to spend time in the fishing capitol of the keys.
10.0 / 10.0
Such a beautiful property. Enjoyed all the wildlife! Wish we could have stayed longer. The home was perfect for the two of us. Very clean and open! Hope to go back soon. Owners were easy to communicate with.
10.0 / 10.0
Enjoy your property very much. Loved the location!!!
10.0 / 10.0
My husband has wanted to fish Islamorada for years. We decided to celebrate our 30th and make his dream come true. This house was an absolute treat! We loved every minute of our time in Islamorada! This property is so convenient, quaint and comfortable. We just loved it! Jackie was wonderful to work with! We will be back!
10.0 / 10.0
Location, location, location…….this place has it all. The amazing sunsets, great location for walking to restaurants and breweries, convenient for groceries and the house was perfect for just the two of us. The owner is the best with great communication too. We will definitely be back in the future.
10.0 / 10.0
The moment we pulled into this property we were in love. Brightly painted murals cover one side of the house and the fence behind. A picnic table sits between the back door and fence, a covered sitting area on the water side of the house, a small water side sitting deck and a large fish cleaning station and boat docking platform.
10.0 / 10.0
Only one word … FANTASTIC 😊
10.0 / 10.0
What a beautiful property! The house is very clean and open. Location is perfect- within walking distance to Lorelei for great food and music and sunsets. We loved how we were tucked in by the mangroves and directly on the water. We got to see a lot of marine life - the neighbors had the hose out for a local manatee one morning. Amenities are fantastic (yes an actual quality kitchen knife and great cookware) and everything in the listing is accurate. Jackie was a fantastic host and helpful with any recommendations in the keys. Very responsive and very friendly. Highly recommend!
10.0 / 10.0
This is the 3rd year in a row that I have rented this property during the first 2 weeks in Dec. It has everything one could want in a vacation rental. Lovely, well appointed, immaculate cottage & surrounding property. Furnished deck on the water ( the perfect place for morning coffee and evening cocktails).. The location is private and far enough off the Overseas Hwy to afford a quiet & peaceful stay yet convenient to everything needed for a great VRBO vacay; close enough so that you can walk to numerous great restaurants, shops, evening entertainment & all kinds of water recreation as well as more of the same within a short Uber, Lyft or Freebee drive so you can virtually park your car for the duration of the stay. I can't say enough great things about this property and it's wonderful hosts and can't wait to return for my 4th visit.
10.0 / 10.0
To summarize…..my husband just asked when can we go back!
10.0 / 10.0
The location is wonderful - quiet, private and made for relaxation. The cottage was very clean and had everything we needed. Owners are very easy to communicate with and recommended many great local spots.
Highly recommend for a great get away!!
10.0 / 10.0
Relaxed and refreshed, we left this cottage after a second stay and both agreed that it was even better than the first visit. Everything we needed with plenty of space for the two of us. Very clean, well thought out, this cottage is a charming nod to old Florida with all of the modern amenities to make our week exactly what we needed. Jackie is a great communicator! We’ll be back again!
10.0 / 10.0
Great location, cute cottage and very accessible to activities and restaurants. Would definitely book again!
10.0 / 10.0
A very nice property tucked away from the main road . Great waterfront access for relaxing or boat activities . Many wonderfull restaurants within a short walking distance . A house with all the amenities you would expect . This rental is not one to be overlooked . We had a wonderfull time and hope to visit again !!!!
8.0 / 10.0
My wife and I were looking for a perfect getaway down in the keys and she stumbled upon this location. We looked at the pictures and said it’s the one! We couldn’t have asked for more. It was our own little private oasis where we could just relax and be in peace but were also short distance to various activities. Best part was the shaded private drive as we walked to a local restaurant.
We will be back!
10.0 / 10.0
Property was well maintained both inside and out. Very cozy but yet spacious. Looking forward to returning sometime in the near future.
10.0 / 10.0
This was the perfect place for me and my husband, there were neighors but there is so much beautiful trees and tropical folage everywhere it made it so private
Great dock for our boat on a deep canal
Pet friendly and perfect location for restaurants and shopping
Will definitely be staying again
10.0 / 10.0
Our stay at Jackie’s home was incredible. The house was extremely clean and cozy. The view from the dock is unbeatable to watch the sun set or see manatees swimming by at all hours of the day. The location feels very private, yet it’s just walking distance from multiple restaurants for breakfast or dinner. We already want to make plans to come back. Jackie was a fantastic host!
10.0 / 10.0
We LOVED our stay here. As advertised, this is a clean, charming cottage. The location is secluded & peaceful with great waterfront views. We enjoyed watching the iguanas and fish. Great host with great communication! Would definitely stay here again!
10.0 / 10.0
Charming cottage !
All you need for a great relaxing vacation.
Close to many activities.
10.0 / 10.0
The cottage was excellent and as advertised. The privacy was appreciated and the adjacent canal provided much enjoyment viewing the manatees and the fish. The kitchen was well stocked, the grill works great and the sunny dining area made for fun meals. The king sized bed was comfortable and the on site full sized laundry made life easy. We used the reclining loungers found in the den and enjoyed sitting on the docks in the evenings. The small dock made for a perfect coffee spot. We would definitely stay here again if staying on Islamorada. Highly recommend!
10.0 / 10.0
For my husband's big birthday, I wanted to surprise him with a trip to the Keys. He's never been! While looking at properties last summer, I asked Jackie a few questions and she answered me quickly. The place is perfect for a couple! The sunsets where gorgeous, the house was comfortable and had everything we needed! We are already talking about when we can go back!
10.0 / 10.0
Great location central to everything, great views private, owners had everything needed plus!! Easy docking for my boat and place to park trailer. Pet friendly, everything needed and wanted for couples, already rented for (3) weeks next year
10.0 / 10.0
My husband and I stayed for 3 weeks over the holidays. It was the PERFECT place to have our boat (close access to ocean/bay & ease of use at their boat dock) and bring our dog (large fenced-in property off a quiet street). The hosts were so responsive to our questions about a good place for a massage, hotel recommendations for friends who came to visit and tons of questions about using a boat in Islamorada. We loved the view from the dock and had Manatees visit often. We would definitely book this house again!
10.0 / 10.0
We spent a week over Thanksgiving and had a fantastic experience. This is an "above and beyond" kind of property. Here are the highlights: 1) Very, very clean 2) Wonderful location, highly walkable to many restaurants and bars 3) Well-stocked with everything you need 4) Super comfortable bed and fluffy towels 5) Outstanding water pressure. We will definitely be back to this property.
10.0 / 10.0
We can’t say enough good things about this sweet cottage in Islamorada. We have been lucky enough to stay there several times now, and each time …. as soon as we pull in the driveway , you are reminded of what a magical place it is. Places this special don’t exist anymore here in Florida … much less in the Keys. The property is absolutely beautiful, with huge trees that rustle in the ocean breeze. The cottage is spotlessly clean, with many small touches that remind you that you are on vacation. It is well equipped, with everything you need to have a fantastic vacation in Islamorada. We can’t wait to visit again in a few months. Bruce & Sherry
5.0 / 10.0
This cottage was everything we'd hoped it would be, It's old time Florida charm with just the right amount of modernizing. We loved the location - enjoyed coffee on the dock every morning, watched the iguanas, manatees and birds. Jackie was a wonderful balance of contact - checking in without being intrusive. We'll be back!
10.0 / 10.0
The host was wonderful, the house was old but fixed up very nice, very good experience
10.0 / 10.0
House was perfect and plenty of room for boat/trailer parking. Will definitely be back in the future.
10.0 / 10.0
This is easily the best rental property ive ever stayed in. They thought of everything you may leave at home and had it waiting for you. Clean and smells nice, felt like being at a home away from home. Jackie was so helpful and made sure we were good to go with everything
10.0 / 10.0
Awesome stay
Place was super clean and perfect for what we were looking for. The dock had tons of fish to enjoy and we even had a family a 5 manatees come hangout for a while!
10.0 / 10.0
Great location
This is a great location if you want to be close to all things Islamorada and/or have a boat. The house is immaculate, the bed super comfortable, and again, the location. It was nice to sit on the dock and listen to the music from Lorelei and be a very short drive to other restaurants. The Square Grouper is a must-visit for lunch or dinner and we enjoyed many of Jackie's other recommendations, including the Lorelei which has the best drink prices.
I always look at a property from the lens of "if this was mine." On the inside, a bench is badly needed in the shower as something to balance on when shaving . (The water pressure though is fantastic.) On the outside, the mangroves and other shrubs need to be cut back along the canal which would help aesthetically and with launching a kayak. We've owned kayaks for 20 years and have been all over. It's obvious where people have launched; I have no idea how they're getting out. That said, we loved our stay and will keep this on our shortlist for a future visit.
10.0 / 10.0
Perfect De-stress Spot for a Couple
We've stayed at this lovely cottage 5-6 times in the past 9 years. Every time it's like coming home. The location on a canal with a dock just yards from the bay is perfect for a kayak or boat. Recent updates to the bath and kitchen (there's now a Keurig) were a welcome surprise. You'll find it's equipped with all your needs and the king bed is comfortable.
Jackie is an awesome host. She's always easy to contact if needed, helpful and friendly.
The Loreli waterfront bar and restaurant is a short walk. Expect a 1-1/2 hour wait for a table during dinner hours. Michael Trix's magic show M/W/F after sunset is awesome!
There are many shops and eateries in the Village area worth checking out
We'll be back next year!.
10.0 / 10.0
Islamorada Gem
Nice quiet waterfront retreat, close to everything you need, restaurants, bars, groceries and shopping. Jackie was a great host, she gave us several great places to check out during our stay. The house was clean and well equipped with everything you need. If you're looking for a relaxing convenient place in the Keys, you won't be disappointed.
10.0 / 10.0
Shh. Secret
Both the house and the host were wonderful. The location is second to none for Islamorada and the house has plenty of historic charm. Despite being just down the street from a popular island restaurant, the setting is extremely private. I plan to return as many times as possible.
10.0 / 10.0
Quiet Islamorada lodging, gulf view
House was just as presented. A classic
charming Florida Keys retreat. Saw manatee and a variety of fish. Grateful we could bring our dog. This was our first booking with VRBO. Received prompt and pleasant response from owner.
10.0 / 10.0
First getaway since covid
Just what we needed
10.0 / 10.0
Excellent stay
Will go back!
10.0 / 10.0
In the Heart of Islamorada—Perfect Spot
We enjoyed our stay so much! The outside space was stellar with plenty of docking space and a little deck next to the water that was perfect for viewing the sunsets. Manatees were frequent visitors and the sheltered canal area was great for practicing paddle boarding.
So many restaurants and shops were within walking distance, with the Lorelei being two minutes away. Absolutely amazing location. The house is very spacious and comfortable. I enjoyed the “spare” bedroom that we used as a spot to store fishing rods etc and my yoga mat. We thank the owners for their great communication and would love to book again. Highly recommend.
FAQs
How much does this cottage cost compared to others in Upper Matecumbe Key?
The average price for a rental in Upper Matecumbe Key is R 9,485 per night. This rental is R 3,966 less expensive than the average.
Is parking included with this cottage?
Yes, parking is listed as an amenity at WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei. For more information, we encourage you to contact the property about where to park.
Is there a pool at this cottage?
We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.
Is WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei pet friendly?
Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei?
We found 10 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and parking.
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