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WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei

Waterfront cottage with kitchen and patio

Photo gallery for WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei

Exterior
open water views from dock
Enjoy the view !
Living room. Original open beam ceiling and floors.
Conch style living room

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 2102.2 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Barbecue grill
  • Kitchen

Explore the area

View map
  • Place, Florida Keys Brewing Co.
  • Place, Theater of the Sea
  • Place, Bud n' Mary's Dive Center
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)

Rooms & beds

1 bedroom (sleeps 2)

Master

1 King Bed

Office 1

1 Single Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei

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 ! :)

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Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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Exterior
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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

Pets allowed: dogs less than 9 kg per pet (limit one pet total)
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Smoking

Smoking is not permitted
Please NO smoking !!
NO FISHING FROM DOCK
No swimming from dock. No diving or jumping from dock
No events at the property

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Islamorada

Located on the waterfront, this cottage is in Matecumbe, a neighbourhood in Islamorada. Keys History & Discovery Center and MoradaWay Arts & Cultural District are cultural highlights, and some of the area's landmarks include Hurricane Monument and Indian Key Historic State Park. Discover the area's water adventures with kayaking, snorkelling and waterskiing nearby, or enjoy the great outdoors with cycling.
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Map
Islamorada, FL

What's nearby

  • Islamorada Brewery & Distillery - 6 min walk - 0.5 km
  • Florida Keys Brewing Co. - 14 min walk - 1.2 km
  • Windley Key Fossil Reef Geological State Park - 6 min drive - 5.0 km
  • Theater of the Sea - 6 min drive - 5.3 km
  • Bud n' Mary's Dive Center - 7 min drive - 4.7 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 39 min drive

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min walk
  • ‪Wendy's - ‬4 min walk
  • ‪Islamorada Fish Company - ‬17 min walk
  • ‪The Trading Post - ‬9 min walk
  • ‪Bayside Gourmet of Islamorada - ‬13 min walk

Frequently asked questions

Is WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 9 kg per pet.

What time is check-in at WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei?

Check-in begins at 3:00 PM.

What time is check-out at WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei?

Checkout is at 10:00 AM.

Where is WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei located?

Located in Matecumbe, this cottage is within a 10-minute walk of Keys History & Discovery Center, Islamorada Brewery & Distillery and Matecumbe United Methodist Church. Florida Keys Brewing Co. and MoradaWay Arts & Cultural District are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 126 out of 128 reviews
Rating 8 - Good. 1 out of 128 reviews
Rating 6 - Okay. 0 out of 128 reviews
Rating 4 - Poor. 0 out of 128 reviews
Rating 2 - Terrible. 1 out of 128 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Janice H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jackie is wonderful to work with and the property is as advertised. It is in a beautiful location on the gulf with a private dock. It has a nice kitchen and was very clean. We had a great time!
Stayed 7 nights in Oct 2025

10/10 Excellent

Denise A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent time in Islamorada! Home was perfect! Clean home with all the necessities included! Owner, Jackie, was very attentive and a pleasure to work with. We were able to ride our bikes to local restaurants, bars and shops. Highly recommend!
Stayed 7 nights in Oct 2025

10/10 Excellent

Cheryl H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean, comfortable cottage. We loved the access to the water and enjoyed the wildlife. The location was convenient to restaurants, shopping, and local attractions. Thank you Jackie! We so enjoyed our vacation!
Stayed 6 nights in Sep 2025

10/10 Excellent

Chase M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location, Clean, Communication

We have a lovely stay and plan to book again! This booking is a great value and we were delighted they allow small dogs! The house is immaculate- right on the water with a dock, was very clean, well maintained, and has everything you could need for a stay (grill, cooking supplies, extra blankets, etc). Jackie the host was incredibly sweet and responsive. Thanks for everything, be back soon!
Stayed 7 nights in Jun 2025

10/10 Excellent

Darlene K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday getaway

I wish I could give the property and Jackie the host a 10 star review. Everything was exactly as described. We had to cut our stay a little short because of our dog having separation anxiety at the dog sitters. Kitchen well stocked with coffee, spices,oil etc. Will definitely stay here again next time we are in the Keys. Fishing was great, Turtle Hospital worthy of a visit and a plethora of fantastic restaurants . Best VRBO experience we have ever had.
Stayed 4 nights in Jul 2025

10/10 Excellent

Jennifer J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent!

Great location, cute cottage and very accessible to activities and restaurants. Would definitely book again!
Stayed 4 nights in Oct 2023

10/10 Excellent

Bill S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Couldn't have been more pleased, great accommodations, great location.

Property was well maintained both inside and out. Very cozy but yet spacious. Looking forward to returning sometime in the near future.
Stayed 4 nights in Sep 2023

10/10 Excellent

Kyle H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place and amazing location

House was perfect and plenty of room for boat/trailer parking. Will definitely be back in the future.
Stayed 3 nights in Aug 2022

10/10 Excellent

LuAnne P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming Cottage

Charming cottage ! All you need for a great relaxing vacation. Close to many activities.
Stayed 7 nights in Apr 2023

10/10 Excellent

Charlotte A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Spot in the Keys!

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.
Stayed 6 nights in Jul 2024

10/10 Excellent

Jerri G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy little cottage

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
Stayed 12 nights in Aug 2023

10/10 Excellent

Joe M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Islamorada Escape

Lorelai is a perfect getaway spot that radiates Florida Keys charm. Surprisingly spacious and cozy at the same time with great water views, front row seats to legendary sunsets and a short stroll to waterfront dining with live music most nights. Our host, Jackie, made the stay seamless and the house is well-stocked with everything you'd need to enjoy yourself. Islamorada is a convenient location for a keys road trip adventure - Key West is just a couple hours away and our day trip there was awesome!
Stayed 5 nights in Oct 2024

10/10 Excellent

Maureen F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Great Choice

The property and quiet location provide a relaxing vacation. Located to so many restaurants and stores. The house is very clean and well taken care of. Beautiful views, friendly neighbors, and plenty of dock space to enjoy the fish, manatees, iguanas, and birds.
Stayed 22 nights in Feb 2022

10/10 Excellent

Brian G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our Florida chatue

Only one word … FANTASTIC 😊
Stayed 20 nights in Feb 2024

10/10 Excellent

Tammy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Islamorada

Great location and property. Very comfortable and well stocked. Perfect set up with convenient boat dock. Would definitely stay again. Everything you need is within a couple of miles. Easy in and out at boat ramp just down the block and access to both Atlantic and Gulf in a short boat ride.
Stayed 7 nights in Jun 2021

10/10 Excellent

John B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wow! Awesome everything…..

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.
Stayed 7 nights in Apr 2024

10/10 Excellent

Mike P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We plan on returning

Very nice home on the water. Nicely stocked. Exactly as advertised. You won’t be disappointed!
Stayed 10 nights in Jun 2019

10/10 Excellent

Patrick J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

First getaway since covid

Just what we needed
Stayed 5 nights in Mar 2022

10/10 Excellent

Jennifer D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection

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!
Stayed 5 nights in May 2023

10/10 Excellent

Donna W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Vacation Home & Location In Islamorada

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!
Stayed 20 nights in Dec 2022

10/10 Excellent

Lois S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Getaway

We had a wonderful Thanksgiving week. 2020 is a stressful year and this was the perfect place to self distance and still enjoy the wonderful outside. We kayaked sat on the dock, and watched the manatees. Did some fishing and just relaxed. Jackie was so easy to communicate with and we throughly enjoyed our stay. Cottage was just as described in photos
Stayed 7 nights in Nov 2020

10/10 Excellent

Noreen M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

OUTSTANDING STAY AT THIS PROPERTY

This is a cozy and comfortable home, in a great location, and with great outdoor space, landscaping and beautiful views! We stayed for two weeks and had a fantastic time....wished we could have stayed longer! My husband fished from the dock, while I enjoyed seeing manatee everyday!! Lots of other marine life, birds, and lizards to watch as well. Perfect location for walking each day and close to many great restaurants. Jackie is a wonderful person and very accommodating!! I can't say enough about this location and how much we enjoyed everything about it....positive vibes!!
Stayed 14 nights in Oct 2021

10/10 Excellent

Dana A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful birthday surprise!

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!
Stayed 7 nights in Mar 2023

10/10 Excellent

MARY

Liked: Cleanliness, check-in, communication, location, listing accuracy

LOVE THIS PLACE

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.
Stayed 14 nights in Dec 2023

10/10 Excellent

Paul R., Atlanta, GA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wow! Privacy and great location!

Our perfect Christmas Vacation! This is Florida Keys charm with an absolutely stunning location. The pictures do not do it justice. There is a new front door and a cool mural on the front of the house. We had manatees swimming right in front of the docks. If you have a boat, there is plenty of docking space. We had a 23' deck boat for the week and could have docked another boat there and still had another dock to sit on and enjoy the waterfront. It was very private and and quiet. We will definitely book this again! We loved it and it is the best "chill" spot we have ever visited in our 30 year marriage. Paul and Kathy
Stayed 8 nights in Dec 2021

About the host

Hosted by Jackie

Host profile image

Why they chose this property

Great location in Islamorada ! Close to everything yet private as well.

What makes this property unique

Experience old Keys...... think Hemingway days and Key West style conch bungalow. .......that is what many of our guests say!

Languages:

English
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