Waterfront Beach 2house Historic Home on 2.5 acres

Historic Shadow Point from Water
Historic Shadow Point from WaterBeach funBeach from waterpath to waterView from middle dock of main housepaddleboarding by middle dockour fleet of boats that come with rentalnorth side of propertyswing with a viewMahogany with Pineapples PathSouth gardenWedding TrellisNorth pointfront of house from waterback property Gumbo Limbosback of housesDining area that seats 14view of kitchen from livingroomKitchen in Main houseView from kitchen windowPorch of Main Housemaster bedroom with private bathSunrise room with private bathView of Cottagecottage livingroomcottage porchOne of two bedrooms in Cottagenorth bench on middle dockKayak that goes with housesailboat that comes with rentalprivate secluded beach on propertypaddleboarding by main dock -clear waterrampOne of Many Palmssunrise on Largo SoundLight on Gumbo LimbosAll Orchids grown on the property
“ Excellent ”
3 Reviews



Bedrooms: 6
Bathrooms: 4.5
Sleeps: 16
Type: Home
Per week: $6,000 - $7,300
Per month: $17,000 - $20,000
Pets allowed: Yes
Internet: Yes
Description of the Key Largo vacation home rental
'Shadow Point' estate offers an exclusive retreat for vacationers desiring an intimate and private setting. This vacation rental is perfect for boaters, kayakers, canoers, divers and fishermen and can comfortably accommodate family retreats, workshops, weddings, and film shoots. This historic one-of-a-kind estate offers a glimpse of Key Largo as it was at the turn of the century. With its original Dade County hard wood floors, sinks in every room and unique pocket slider windows, the two guest houses offer the vacationer a chance to step back in time and experience the charm of days gone by. Located on a hammock point, the 2.5 acre estate is filled with lush tropical trees and a 260 degree view of pristine Key Largo Sound. The best dive reefs in the country are just a short boat ride away.

Four days or more is required so you can get time to relax and experience all that Shadow Point offers.
Area Information
History: Shadow Point was built in 1917 by a ship captain and later bought by Chicago Industrialist, Frank Sweeting, for his fishing friends. After his daughter and son-in-law, Lelia & Marvin Adams, inherited the property, Adams spearheaded the design and construction of the nearby canal that links the bay side with the ocean side of Key Largo. Named for the beautiful changing shadows and light that filter through the tropical hardwood hammock, Shadow Point is located on Key Largo Sound, the ocean side of Key Largo. Today, this estate offers the same relaxed atmosphere and seclusion of an earlier era. The 2.5 acre point is filled with lush tropical trees including Buttonwood, Gumbo Limbo. Lignum Vitae, and Key Lime. With a 260 degree view of pristine Key Largo Sound, Shadow Point is an exclusive retreat for those desiring an intimate and private setting.

Accommodations : The main house has four large bedrooms with twin beds in two rooms and two master bedroom with king beds and private baths in the other rooms. The large kitchen is user-friendly and perfect for viewing the lovely trees and water while sipping coffee. The dining table can seat fourteen for family gatherings. A large breezy porch with hammock and two daybeds runs the length of the house and offers a panoramic view of the water. The guest cottage has a small kitchen, two bedrooms that each contain twin beds, a living room with a queen pullout couch, and a charming screened porch. Air conditioning, cable TV and wireless Internet add comfort and convenience. This vacation rental is perfect for boaters, divers and fishermen along with being large enough for family retreats, workshops, weddings, and film shoots. We prefer to rent both houses together so you can experience total privacy and seclusion. Four days or more is required so you can get time to relax and experience all that Shadow Point offers.

This 2.5 acre ocean side estate is located at the north end of Key Largo Sound just a one hour drive from Miami International Airport at mile marker 103 on US 1 South.

About the owner

Owner Profile

Marlee or Dylan Matheson

Marlee or Dylan Matheson


Availability Calendar



Begins Ends Week
Weekly Monthly Min
Nov 01 2015 Jul 08 2016 - - $7,300 $20,000 1 Week
Sep 09 2016 Nov 06 2016 - - $6,000 $17,000 1 Week
Jun 01 2017 Aug 31 2017 - - $6,300 $18,000 1 Week
Check In: 4 p.m. Check Out: 11 a.m.
Lodging tax: taxes of 12.5% and cleaning of $400
Deposits: Half of rent to hold your spot.Final payment due 60 days before start of the rental plus $1500 security deposit. Add $500 for holidays and special weeks. We accept personal or cashiers checks only made out to Shadow Point LLC and mailed to 3800 Wood Ave., Miami, Fl. 33133 Please call before sending any money.
Payment Options: Cashier's Check, Money Order, Personal Check
Other Fees: There is a $100 charge for each guest exceeding 12. Extra charge for holidays and special weeks. No more than 16 allowed sleeping on the property. We only rent by the week unless there is a last-minute change and a spot becomes available. For weddings and large events there will be an added fee charge for amenities depending upon amount of parties and persons attending each event, such as rehearsal dinner, wedding, reception, and brunch and beach party the following day. Please contact us.



  • Beds

  • 2 King Beds
  • 10 Twin Beds
  • 1 Sofa Bed
  • 2 Cribs
  • Features

  • Air Conditioning
  • Full Kitchen
  • Linens Provided
  • Porch
  • Beach Chairs
  • Hardwood Floors
  • Outdoor Shower
  • Screened Porch
  • Beach Towels
  • Heating
  • Parking Included
  • View (Water)
  • Beachfront
  • High Speed Internet
  • Patio
  • Waterfront
  • Deck
  • Kayak
  • Pet Friendly
  • Wheelchair Accessible
  • Dock/Boat Slip
  • Appliances

  • CD Player
  • Gas Grill
  • Oven
  • Stove
  • Ceiling Fan
  • Hair Dryer
  • Radio
  • TV (Cable/Satellite)
  • Charcoal Grill
  • Ice Maker
  • Refrigerator (Full)
  • Telephone
  • Coffee Maker
  • Iron
  • Refrigerator (Mini)
  • Toaster
  • DVD Player
  • Microwave
  • Stereo
  • Washer/Dryer
  • Dishwasher
  • Activities

  • Beach
  • Restaurant
    (<1 mile)
  • Live Entertainment
    (1 mile)
  • Tennis
    (2 miles)
  • Canoeing
  • Sailing
    (<1 mile)
  • Grocery Store
    (2 miles)
  • Windsurfing
    (2 miles)
  • Kayaking
  • Scuba Diving
    (<1 mile)
  • Park
    (2 miles)
  • Children's Pool
    (3 miles)
  • Ocean
  • Snorkeling
    (<1 mile)
  • Playground
    (2 miles)
  • Water Park
    (3 miles)
  • Boating
    (<1 mile)
  • Aquarium
    (1 mile)
  • Pool
    (2 miles)
  • Movie Theater
    (13 miles)
  • Fishing
    (<1 mile)
  • Bicycling
    (1 mile)
  • Shopping Area
    (2 miles)
  • Zoo
    (25 miles)
  • Parasailing
    (<1 mile)
  • Deep Sea Fishing
    (1 mile)

Other Vacation Rental Amenities
Activities & Attractions: Swimming, sailing, paddle boarding, and kayaking are available on site. Boat rentals, parasailing, reef diving are nearby. Local attractions include Theater of the Sea, a marine mammal park, 5 miles south; Swim with the Dolphins, 3 miles south; and the Key Largo Community Park, with swimming pools, tennis courts, and a fitness trail. Shopping and restaurants are only minutes away. The famous Pennekamp State Park is right down the street for all for your diving, snorkeling and boating needs.

Reviews (3)

Reviews for this vacation home rental in Key Largo, Florida

Have you been a guest of this property? Write a review!
“ Excellent ”
3 reviews
Tracey Wasylik

Tracey Wasylik

Fort Lauderdale, FL

Beautiful and charming wedding venue

November 20, 2015

We chose to host our wedding at Historic Shadow Point and it left a lasting impression. The grounds are beautiful and meticulously kept. The houses are charming and comfortable. The owners are warm, inviting, and very good at communicating. I would definitely suggest taking advantage of the Kayaks; paddling around the mangrove islands was a great way to see the nature of the Keys.

Marlee or Dylan Matheson

Owner's reply:

I believe you chose the perfect venue to host your wedding. Historic Shadow Point is magical and that is why we want to share it with others.The moonlight over the water is something that you can't forget! Nature at its best.

Tamsen Valoir

Tamsen Valoir


Wonderful Visit!

August 12, 2014

We loved the 1920's home, period furniture and all of the art displayed on the walls. It was like stepping back in time and felt very much like a family home. With two houses, we had space for all the adults in one and all the teens were in the smaller house, giving everyone a space for hanging out. Plus, being on two acres felt very private! Having the kayaks, paddle boards and snorkels was one of the best features--we kayaked every morning, followed by sun salutations (yoga) on the beach, and then snorkeling a few times very day. The house was well equipped, linens, towels, shampoo, blender and coffee pot all ready for use, although in August one of the AC units struggled to cool the room. The water is tea colored and visibility varied with the weather. Most of the water was shallow with lots of sea grass, but in the lagoon in front of the castle there are coral banks with lobsters (lots) and many more fish. We also saw sharks in the deep water and a sea turtle there. Being so close to Pennekamp park was great too, and we took a tour out in the Atlantic for a much better selection of coral, sea fans, parrot fish, and various angels. We will definitely go back!

Marlee or Dylan Matheson

Owner's reply:

So Glad you had a good time and enjoyed Historic Shadow Point. Sounds like you saw quite a bit of wildlife just off the dock. It is a pleasure to have renters that appriciate the historic items and the art that the house offers, and the privacy of the place. Please come back soon.

Maggie Leonard-Kerrigan

Maggie Leonard-Kerrigan

West Palm Beach, FL

The family reunion I fantasized

August 24, 2013

This property allows a family to enjoy a home together . It was everything I imagined. My imagination is very Vivid . Thank you

Marlee or Dylan Matheson

Owner's reply:

Thank you!

Owner Supplied Testimonials

Wonderful Retreat
Beth Coconut Grove, Fl
Review Submitted: August 19, 2010 Date of Stay: August 2010
Shadow Point was the perfect family escape for my husband's 50th. The house is charming and wonderfully comfortable, but the real surprise is out the back door. Beautiful views and complete privacy on Key Largo Sound. Everything inside and out was extemely well maintained. Marlee made sure we had everything we needed and quickly responded to any questions we had. The dock (had new railing bumpers, no need for fenders) was perfect for our 30' boat. It's a quick cruise to either the ocean or bay. If you want to experience old Key Largo in comfort and serenity, you will love Shadow Point. We look forward to returning. Thank you, Marlee!
Recommended for: Age 55+, Pet-friendly, Adventure Seekers, Girls Getaway, Families with Teenagers, Romantic Getaway

Review Submitted: April 2, 2010 Date of Stay: March 2010
I have to say this is a magnificent old world, charming property. We stayed there 9 days and would recommend it to anyone and would not hesitate to come back again. I despise staying in a house where your look out your window and see in the neighbors windows. As congested as Key Largo can be, this is a beautiful private refuge. Thank you for sharing this gem.
Recommended for: Age 55+, Adventure Seekers, Girls Getaway, Families with Teenagers, Families with Young Children, People with Disabilities, Romantic Getaway

Family Christmas
AlbertC Raleigh, NC, US
Review Submitted: January 9, 2010 Date of Stay: December 2009
Our entire family spent as week at Shadow Point and found it a wonderful experience. The house and the cottage were definitely not modern motel rooms. They were more like museums where every day you discover new pieces of art. The setting was spectacular. The landscaping was like a tropical forest. Everything worked. It was helpful to have two kitchen units to keep up with all of food prep and supplies. Our children were able to swim off of the property as well as having easy access to the snorkel and dive boats. I agree with the owner that occupancy of both the house a cottage is best. We needed the space but it would have been difficult to have had another party in the cottage. Although there was fairly active surrounding neighborhood, it did not intrude on the location.

If the size and location fits you needs, it is a great deal.
Recommended for: Age 55+, Sightseeing, Families with Teenagers, Families with Young Children, People with Disabilities

55th Birthday Party Blast!
Robin & Mark Tularosa, NM
Review Submitted: August 29, 2009 Date of Stay: August 2009
This was the third time I've celebrated my birthday at Shadow Point and the fifth time I've met there with a large group of people! All 14 of us left happy and relaxed. It was the best the place has ever looked - Marlee has put a LOT of work into the house. It is the most gorgeous, special place ever! A blast from the past with all the conveniences at the same time. It's an art gallery, a history lesson, and a step into yesterday, all on two and a half private fenced acres! With all there is to do in the Keys, once you step foot in Shadow Point, the only time you'll want to leave is for a beer-run or some amazing fresh-caught fish at the fish market. Stores are conveniently close. Even though there are some great restaurants around, we stocked up and made all our meals there. We're getting another group together to go back in May 2010 for an Artists' Retreat. It's an absolute paradise for artists and water-lovers. Marlee has made sure her guests will be comfortable, happy, and want for nothing! Thanks for another fantastic time and we can't wait to come again next year!

Shadow Point vacation
Durham, NC Durham, NC
Review Submitted: June 24, 2009 Date of Stay: June 2009
My family of 6 had a great time during our one week vacation at Shadow Point! The two houses were ideally located to satisfy the diverse interests of our adult children. The highlights of our week included snorkeling on nearby Pennekamp State Park reefs, fishing among the mangroves, and exploring local sites. After busy days, we enjoyed coming home to the charm, comforts, seclusion, and waterfront vistas of Shadow Point.

Durham, NC
Recommended for: Girls Getaway, Families with Teenagers, Families with Young Children, Adventure Seekers, Pet-friendly, Sightseeing
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5/5Graduation Trip
Alysa Atlanta
Review Submitted: June 21, 2009 Date of Stay: May 2009
We all came down for a last week together after graduating from high school. It was fabulous! Just a few parents and my closest friends. What a way to end our time together.
The house was just how I remember from when I was a little kid, the view was spectacular, and by the end of the week no one wanted to leave.
Everything from the snorkeling to the fishing to the shopping in town was so much fun. I really recommend this getaway for anyone looking to sit back, relax, and take in all that natural beauty!
Recommended for: Girls Getaway, Families with Teenagers
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5/5Most relaxing week I could imagine!
Patti & Dusty Cambridge, Maine
Review Submitted: March 18, 2009 Date of Stay: March 2009
My husband and I rented just the cottage for 9 days in March. Marlee (the owner) was concerned it might be too rustic, on its own, with no TV. We were delighted! (And it did have wifi...) our only interruption was when a ten pound iguana fell out of a tree near the porch (He was very embarrassed). The kitchen had everything we needed, the decor reflected the house having been in the family for almost 100 years, and the property itself is everything the previous reviews say, and more. We had another couple visit for a few days, and had plenty of room - could even have had more visitors with the fold-out in the living room. A historic property that everyone in Key Largo seems to know and love!
Recommended for: Girls Getaway, Families with Teenagers, Romantic Getaway, Families with Young Children, Age 55+, Sightseeing
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5/5Wonderful Family Vacation
Malcolm,Kevin and Susan Norwalk,CT,USA
Review Submitted: March 13, 2009 Date of Stay: February 2009
I spent a week here with children and grandchildren. It was truly a step back in history to a charming and fascinating house located on a most beautiful and unique piece of property providing complete privacy. The spectacular sunrises are not to be missed.
The description is accurate, the property well maintained and Marlee was always helpfull.
The kids and adults enjoyed swimming, kayaking, sailing and snorkeling on the property as well as visits to Pennekamp State Park and Everglades National Park. We all enjoyed dinner at the Fish House and Mandalay resaurants.
Everyone of all ages enjoyed our stay and did not want to leave. Thanks Marlee for a great week.
Recommended for: Families with Teenagers, Families with Young Children, Adventure Seekers, Age 55+
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Frequently Asked Questions

Q: What are the most fun things to do at your vacation rental?
A: Snorkeling. paddle boarding, kayaking, swimming, and just relaxing are the things you can do right from the property. Of course we provide you with all the toys needed for a great day at our beach.
Q: What makes your vacation rental special?
A: We are a very secluded rental. You don't feel that you have any neighbors and we offer a 300 degree view of the water.

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Page Views This month: 200 This year: 3,589 Since listed: 23,483
Last updated: November 29, 2015

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$6,000 / week


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