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

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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

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Walkable and wonderful
    Guests love the walkable location for its easy access on foot.
  • Discover nearby landmarks
    Walk to Florida Keys Brewing Co.
1 bedroom1 bathroomSleeps 2

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Islamorada, FL
  • Place, Islamorada Brewery & Distillery
    ‪6 min walk‬
  • Place, Keys History & Discovery Center
    ‪6 min walk‬
  • Place, Florida Keys Brewing Co.
    ‪14 min walk‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪46 min drive‬

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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House Rules

Check in after 3:00 PM
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

Property # 429859vb
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. Hurricane Monument and Indian Key Historic State Park are local landmarks, and the area's natural beauty can be seen at Windley Key Fossil Reef Geological State Park and San Pedro Underwater Archaeological Preserve State Park. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven. Discover the area's water adventures with kayaking, snorkelling and waterskiing nearby, or enjoy the great outdoors with cycling.
View more Cottages in IslamoradaOpens in a new window
Map
Islamorada, FL

What's nearby

  • Islamorada Brewery & Distillery - 6 min walk - 0.5 km
  • Keys History & Discovery Center - 6 min walk - 0.5 km
  • beach near Islamorada - 7 min walk - 0.7 km
  • Matecumbe United Methodist Church - 9 min walk - 0.8 km
  • Florida Keys Brewing Co. - 14 min walk - 1.2 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
  • ‪Bayside Gourmet of Islamorada - ‬13 min walk
  • ‪The Whistle Stop Pub & Grill - ‬11 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.

How much is parking at WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei?

On-site parking is available at the property.

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 Lorelei Restaurant & Cabana Bar, Keys History & Discovery Center and Islamorada Brewery & Distillery. Matecumbe United Methodist Church and Florida Keys Brewing Co. are also within 15 minutes.

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. 138 out of 140 reviews
Rating 8 - Good. 1 out of 140 reviews
Rating 6 - Okay. 0 out of 140 reviews
Rating 4 - Poor. 0 out of 140 reviews
Rating 2 - Terrible. 1 out of 140 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Katherine p.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Apr 2026
Response from VrboOwner on 12 May 2026
Thank you for choosing our place! Glad you enjoyed your visit to Islamorada! Thanks and take care :)
Verified

10/10 Excellent

Char & Bill S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It’s our third time here and we absolutely love it.
Stayed 5 nights in Feb 2026
Response from VrboOwner on 22 Feb 2026
So thankful to have amazing repeat guests like the two of you! Thanks for loving our little place! Look forward to your next visit :)
Verified

10/10 Excellent

Jerry M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 6 nights in May 2026
Response from VrboOwner on 6 June 2026
Yay!! So glad you had a fun visit. Thanks so much for choosing our place and being great guests!
Verified

10/10 Excellent

Olivia S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exceptionally clean and the most peaceful location. We loved reading on the dock every morning and walking to the nearby tiki bar. We would love to come back.
Stayed 5 nights in Mar 2026
Response from VrboOwner on 10 Mar 2026
Thanks so much for choosing our place. I am so happy you had a fun time! We hope you visit again soon. Take care and thanks for being great guests!
Verified

10/10 Excellent

Nancy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay at the cottage! Host was very responsive, house was clean, spacious, comfortable. So fun to have breakfast out on the deck, saw 2 manatees! Nice location for walking around. We went to Lorelei's several times to eat and also listen to music.
Stayed 5 nights in Mar 2026
Response from VrboOwner on 3 Apr 2026
Thanks for being great guests! And so happy you had a fun visit :) Take care and hope you visit again soon.
Verified

10/10 Excellent

Brad H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house and location
Stayed 6 nights in Dec 2025
Response from VrboOwner on 27 Dec 2025
Thanks so much! Glad you guys had a fun visit and chose our place to celebrate Christmas 💕🌲
Verified

10/10 Excellent

Renea K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and super host! Loved this place!
Stayed 4 nights in Aug 2025
Response from VrboOwner on 3 Sept 2025
Thanks so much for choosing our place! Glad you guys had a fun visit. Take care!
Verified

10/10 Excellent

Hannah M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was very welcoming and sent recommendations prior to our trip. Loved the home, it was a great location and could tell it was really clean!
Stayed 5 nights in Oct 2025
Response from VrboOwner on 15 Nov 2025
Thanks for being great guests! Take care:)
Verified

10/10 Excellent

Frede A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the house, the property, and the host. Great location. Can’t wait to return!
Stayed 4 nights in Oct 2025
Response from VrboOwner on 22 Oct 2025
Thanks for being AMAZING guests!! and will stop by and meet you next time you visit. Thanks so much for choosing our place to stay in Islamorada. Take care :)
Verified

10/10 Excellent

Hans-Christian L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A truly wonderful place. Wouldn't change a thing. Jackie was great and took great care of managing everything to do with our stay at this rental!
Stayed 6 nights in Dec 2025
Response from VrboOwner on 15 Dec 2025
Thanks for being awesome guests and choosing our place. Hope you have a beautiful Christmas and New Year!
Verified

10/10 Excellent

Hillari J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was extremely welcoming checked to make sure we would arrive before dark if not she offered to go and cut on the lights. House was adorable, super clean and so many cute touches like string lights on covered patio and timed solar lights that popped on at night great added touches! Location was convenient to restaurants and shops.
Stayed 7 nights in Dec 2025
Response from VrboOwner on 6 Jan 2026
Thanks so much for taking time to write review! So glad you guys had fun and that you rebooked for later this year! Thanks for being great guests, Happy 2026!!
Verified

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
Response from VrboOwner on 13 Oct 2025
Thanks for being great guests!! I’m so happy that you had a fun time! Take care:)
Verified

10/10 Excellent

Robert H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 14 nights in Apr 2026
Response from VrboOwner on 22 Apr 2026
Robert, thank you so much for taking the time to write such a beautiful review of our property! You guys were such awesome guests and I am so glad you had a fun time. Thanks again for choosing our place for your visit to Islamorada! Take care :)
Verified

10/10 Excellent

Debbie C.

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

Islamorada Stay

We had such a wonderful time during our short stay in Islamorada. Over the years we have been to Islamorada many times and have stayed at many different places, and this was by far our favorite! Very relaxing and spectacular sunsets!
Stayed 4 nights in Jul 2025
Response from VrboOwner on 26 July 2025
Debbie thanks so much! We look forward to your next visit! And it was so nice meeting you guys. Take care :)
Verified

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
Response from VrboOwner on 10 Sept 2025
Thank you so much for choosing our place and being wonderful guests. Take care and thanks again.
Verified

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
Response from VrboOwner on 26 Oct 2025
Thanks so much for being awesome guests! Hope you guys visit again. So glad you had a fun time :)
Verified

10/10 Excellent

Bobby P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
If you want to experience the Old Florida style Keys, here’s the place! This home is from the 1940’s and has that same charm. So clean and the a/c and heat function top notch. ( I know because I’ve stayed here both when it was hot and cold ) The house is fully equipped with anything you could possibly need to enjoy your stay and plenty of room to dock your boat. The large yard is beautifully landscaped and full of wildlife. Including daily visits from manatees and wading birds. This is perfectly located in Islamorada and within walking distance of Lorelei, Keys History & Discovery Center and more!
Stayed 4 nights in Feb 2026
Response from VrboOwner on 16 Feb 2026
Thank you both so much for always being the best guests! Thanks for the beautiful review! So happy you once again had a fun visit. Take care and we hope you visit again soon :)
Verified

10/10 Excellent

Charles B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We thoroughly enjoyed our stay at Jackie's place. This is a great place and location for a laid back vacation. It deserves 10 stars for all of the aspects of this property. Jackie has taken a lot of care and forethought in preparing this house for visitors. The property offers seclusion, a great tropical vibe, wildlife, and view. The house is comfortable and clean with extensive attention to essentials for a short stay. Jackie stayed in touch to make sure everything was to our satisfaction. It was a chilly week and she could not affect the weather, but otherwise we enjoyed our stay and her attention to our needs.
Stayed 7 nights in Jan 2026
Response from VrboOwner on 4 Feb 2026
Thanks for being great guests and for being such good sports with our very rare super cold south Florida weather this January!! Brrrrr! Glad you had a nice stay in spite of the cold :) Take care and hope you visit again soon. Take care.
Verified

10/10 Excellent

Cardiff S.

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

Great Location and dockage

Excellent location, plenty of parking and dockage for trailers and boats. Very nice quaint setup in the middle of Islamorada.
Stayed 8 nights in Dec 2020
Response from VrboOwner on 29 June 2023
Thanks for being great guests! Come visit us again soon:)
Verified

10/10 Excellent

Cheryl R.

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

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!
Stayed 5 nights in Jul 2022
Response from VrboOwner on 29 June 2023
Thanks so much Cheryl, glad you guys had a great time! Thanks for leaving house so neat and clean. Take care.
Verified

10/10 Excellent

Mike T.

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

Great location

Perfect vacation spot. Quaint and charming house with all the basic amenities needed for my wife and I to relax and bike to all the local spots. Very quiet and private.
Stayed 5 nights in Dec 2024
Response from VrboOwner on 17 Dec 2024
Thanks so much for being great guests! Hope you guys stay again in future. Merry Christmas and Happy Holidays :)
Verified

10/10 Excellent

Gerard L.

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

Vacation getaway!!

Enjoy your property very much. Loved the location!!!
Stayed 4 nights in Apr 2024
Response from VrboOwner on 28 Apr 2024
Thanks for being great guests! Hope you visit us again soon. Take care :)
Verified

10/10 Excellent

Stephanie S.

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

Perfect stay

Solo traveler, great location (walking distance to Lorelei’s). Quiet, nice dock for watching the sunset. Everything I needed for a weekend to reset. Will definitely stay here again!!
Stayed 5 nights in Aug 2024
Response from VrboOwner on 7 Sept 2024
Thanks, Stephanie, for being a great guest and for taking the time to write review. I hope you visit again and get to meet you next time. Take care.
Verified

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
Response from VrboOwner on 29 Oct 2023
Thanks for being great guests! Hope you guys visit again soon. Take care.
Verified

10/10 Excellent

Bobby P.

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

Clean and comfy

The house and property is very beautiful with privacy and plenty of nature. The location is great with lots to do close by. The house has everything you need to enjoy a peaceful vacation
Stayed 4 nights in Oct 2024
Response from VrboOwner on 4 Nov 2024
Thanks for being AMAZING guests!! Thanks for choosing our place to stay in Islamorada. We hope you visit again soon. Take care.

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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