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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Secluded-Perfect for Families, Gatherings, Weddings 2 Historic Homes with Beach

Bedrooms 6
Half Baths1
Space 4,000 sq. ft.
Property type estate
Minimum Stay 7 nights


About the property

2 Houses- total of 6 Bedrooms +Sleeping Porch, 4.5 Baths (Sleeps 16) 2 kitchens

This private stunning place, Historic Shadow Point, is surrounded on 3 sides by water and is the most charming, spectacular and intimate and private property in Key Largo for your vacation rental. With our OWN PRIVATE BEACH, fabulous moon rises over the water, gorgeous sunrises and sunset skies, tropical gardens and, delightful breezes, you couldn’t have a better place for an enjoyable stay. Remember - We are surrounded by water -not on a canal and not near any other homes. A perfect place for kids to swim and snorkel.

Historic Shadow Point estate, an HOA - gated community, 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, film shoots, anniversary parties, and commitment ceremonies. Have your wedding and reception on the property as well as a rehearsal dinner the night before and a beach party brunch the day after the vows. All this without the restrictions of hotels and added expenses for a different venue.

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 hardwood 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 gated Hammock point, the 2.5-acre estate is filled with lush tropical trees and has a 180-degree view of pristine Key Largo Sound. It has its own private beach ready to launch our kayaks and paddleboards that come with the rental or just relax and build your own sand castle. Bring your own boat and tie up at our dock that offers electric and water for boats 40 feet or less. The best dive reefs in the country are just a short boat ride away.

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, Leila & Marvin Adams inherited the property, Adams spearheaded the design and construction of the nearby canal that links the bay side on the ocean side of Key Largo. It is now known by the locals as ' Adams Cut'.

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 2 king beds in the other two. There are private baths in both bedrooms with king beds. 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 stocked kitchen, two bedrooms that each contains 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. The property has 3 docks one of which has electric and water and can take a boat that draws up to 4 feet. This vacation rental is perfect for boaters, divers, and fishermen along with being large enough for family retreats, workshops, and film shoots. We prefer to rent both houses together so you can experience total privacy and seclusion.

ACTIVITIES & ATTRACTIONS: Swimming, sailing, canoeing, and kayaking are available on the 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. We have had numerous celebrations at Shadow Point. Please call for information.

Other Activities: kayaking, canoeing, tubing, boating, paddle boarding

Keywords large property, estate, secluded, private, homeowner association

Beach front, swimming, snorkeling, paddle boarding

Family groups, Historic house, commitment ceremonies Workshops,

Sun, fishing, 3 docks, diving, retreats brunches, rehearsal dinners, receptions, tropical gardens, tropical breezes,


More Details

Marlee Matheson (Owner) Dylan Matheson (manager)
Member since: 2007
Speaks: english, spanish
Response time:
Within 12 hours
Response rate:
Calendar last updated:
January 19, 2018

About Marlee Matheson (Owner) Dylan Matheson (manager)

This property has been in the family for almost 100 years.

Marlee Matheson (Owner) Dylan Matheson (manager) purchased this estate in 1922

Why Marlee Matheson (Owner) Dylan Matheson (manager) chose Anglers Park

This property has been in my family for 100 years. It was one of the first houses built on Key Largo and located in an incredible secluded hammock that instantly takes travelers away from the hustle and bustle of life. I am the 5th generation of owners and I have decided to share this wonderful place.

What makes this estate unique

Like stepping back in time to the lazy days of the 1920's

Guestbook comments from the owner

What can you say about a vacation for 13 people (five grandchildren age 3-8)my wife and me and our three children's families when everything went really well. Shadow Point was wonderful--the large screened porch was the gathering point for adults as they emerged in the morning with their coffees and gradually got prepared for the day. Weather cooperated so much time was spent by children enjoying the small beach and the adults not being fearful of any problems. Kayaks were used by dads and their children and sunning, sitting and reading were much enjoyed activities by adults. The grounds are spectacular with beautiful landscaping right up to the water. The house is equipped with everything that anyone could possibly need; the beds were comfortable and we never ran out of hot water. A day in Key West for some; a day in the Everglades for everyone, and individual excusions to Anne's Beach and other places were perfect. The bottom line is that the house with its charm and comfortableness was the center point that made everyone happy. We hope to be able to return again. A really grand place for a large famility to enjoy! And thank you Marlee for making sure that we didn't worry about a thing!

Recommended for: age 55+, families with young children, families with teenagers, girls getaway, pet-friendly
Mar 2011
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Anglers Park Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
Floor Area:
  • 4000 sq. ft.
House Rules:
  • Max. occupancy: 16
  • Minimum Age Limit for Renters ...
  • pets considered
  • Events Allowed
  • children welcome ...
  • non smoking only ...
Location Type:
  • Beach ...
  • Beach View ...
  • Beachfront ...
  • Ocean View
  • Oceanfront ...
  • Resort ...
  • Water View ...
  • Waterfront ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Activities Guide
  • Air Conditioning
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer
  • Filtered Water
  • Hair Dryer
  • Heating ...
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Living Room ...
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking ...
  • Parking Off Street ...
  • Parking for RV/Boat/Trailer ...
  • Shampoo
  • Sofa Bed
  • Telephone
  • Thermos Bottle
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Catering Available ...
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Freezer ...
  • Grill
  • Ice Maker
  • Kitchen ...
  • Lobster Pot
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster ...
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 14 people
  • 4 Bathrooms
  • 1 Half Bath
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
  • 4.5
  • 6 Bedrooms, Sleeps 16
  • Bedroom 1 - 1 king
    Bedroom 2 - 1 king
    Bedroom 3 - 2 twin/ single
    Bedroom 4 - 2 twin/ single
    Bedroom 5 - 2 twin/ single
    Bedroom 6 - 2 twin/ single
    Cottage living room - 2 sleep sofa /futon
    Sleeping Porch (2 Day beds) one hammock - 2 twin/ single , 2 baby crib , we offer two porta cribs and one cradle
  • King size beds (2) 2 rooms have KING SIZE BEDS and PRIVATE BATHS., Twin or Single Beds (8) 4 bedrooms have 2 twin beds in each room porch has two twin beds, Baby Cribs (2) two pack and play s (1) one pull out queen sofa in cottage.(1) cradle.
  • Audio Tape Player
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Games
  • Games for Kids
  • Music Library
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television
  • Toys ...
  • Video Library
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Boat Dock
  • Boat with Paddles
  • Canoe
  • Child's Swing
  • Deck / Patio
  • Fish Cleaning Table
  • Gated Community
  • Kayak / Canoe ...
  • Large Cooler
  • Lawn / Garden ...
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda
  • Raft
  • Sand Box
  • Screen Porch / Veranda
  • Tennis ...
  • Terrace
  • Unscreened Porch / Veranda
  • Walkway to Water
  • Water Sports Gear ...
  • Long-term Renters Welcome
  • Low Allergen Environment
  • suitable for elderly or infirm
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • health/beauty spa
  • library
  • marina
  • museums
  • playground
  • reefs
  • restaurants
  • water parks
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • outlet shopping
  • paddle boating
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • jet skiing
  • kayaking
  • paragliding
  • parasailing
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
We have 4 single man kayaks and one double kayak, one childs kayak, 2 paddle boards for guests use.


Exceptional! 5/5 -
(14 traveler reviews)

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Secluded-Perfect for Families, Gatherings, Weddings 2 Historic Homes with Beach
average rating of 5.0 based on 21 reviews

A Special Gathering Place

  • 5 of 5

Our family rented Shadow Point for a week in June. We invited our four children, their spouses / boyfriends, and our two young grandchildren. The houses and property make you feel as though you leave behind the stresses of life! The houses are very historic and have colorful and unique furnishings. The property is beautifully landscaped with numerous gathering spots throughout including breezy porches, a fire pit area for evening campfires, a dock area and "beach" area at the waterfront. The owners generously allow use of their beach towels, snorkel equipment, floats, lounge chairs, kayaks and paddle boards. There are several outdoor dining areas. The homes are situated at the end of a residential street behind a gate so there is complete privacy to make you feel like you are in your own little world. We always enjoy preparing large family dinners instead of dining out. The kitchen was very well supplied to meet any cook's needs. There are even bowls and serving platters large enough to be used by a caterer! We commented throughout the week that it was like being at family camp in our own private resort. The property is located on Largo Sound and is VERY convenient by boat to the Atlantic, Floriday Bay or John Pennecamp state park. Marlee was very helpful in giving recommendations for boat rentals. Very highly recommend!!

  • Submitted: Jun 17, 2017
  • Stayed: June 2017
  • Source: VRBO, from HomeAway
Owner's Response: So happy you enjoyed Historic Shadow Point. We love sharing this gem with others and we are always thrilled to hear about your experiences. Do come back and create more memories in Key Largo.
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Pompano Beach, Florida

Never wanted to leave!

  • 5 of 5

Shadow Point is what the Keys are all about; quirky, very laid back, colorful, and casual way of life. Everything inside the home and outside is interesting to look at and leaves you wanting to know its story. So many nooks and crannies outside on the grounds to get lost in.

This was one of two properties I never wanted to have to leave; the other one being in Hawaii. The houses and surrounding land are amazing! So much to see and do, from finding a place to escape and just gaze out at the water, to having fun kayaking, paddle boarding, or snorkeling right in the backyard. There was plenty of room for our party of 15, we never seemed to get in each other's way unless we wanted to.

There was plenty of seating at the spacious dinner table, lots of room to just see and do. Beds were comfortable, kitchen was well-stocked, bathrooms had great towels. The hammock was a huge hit. The porches on both houses were a really comfortable place to read, talk, or just be.

Shadow Point is completely secure and private, but close to everything you could possibly need; grocery, drug stores, restaurants, dive shops and just a short boat ride away is world class diving at Molasses Reef, and numerous wrecks. Marlee and her staff were extremely prompt with communications and attended to our every need. I can’t say enough about this place; so much history! If only the walls could talk. It was an absolute pleasure to stay here and I can’t wait to come back!

  • Submitted: May 12, 2017
  • Stayed: April 2017
  • Source: VRBO, from HomeAway
Owner's Response: So happy that you enjoyed Historic Shadow Point. You are so right. If those walls could talk it would make for an intriguing book. Please come back and discover more fun things to see and do! Marlee
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-Coral Gables, Florida

Best of the Keys!

  • 5 of 5

I've lived in Miami all my life, so I know the Keys pretty well, having visited the Upper Keys to Key West many times. I didn't believe I could be "blown away" by a Keys vacation at this point--but I most certainly was! Shadow Point is the best Keys venue of all the many I've been to. We were surrounded by all the charm, solitude, and wondrous beauty of nature, combined with the comforts of today. The owner/managers sop at nothing to make your vacation in Paradise as special as the photos show. Thanks again!

  • Submitted: Nov 20, 2016
  • Stayed: November 2016
  • Source: VRBO, from HomeAway
Owner's Response: We at Historic Shadow Point try to give you a calm relaxing experience. We try to provide you with all the comforts that you might need for a fun vacation in Key Largo. We are so happy that you enjoyed your stay and do hope you return for another chance to experience our gardens and serene water views.
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Florida at its best!

  • 5 of 5

Shadow Point is Old Florida charm with modern comforts. The houses are brimming with history, art and personality. And yet there is everything you might want – a great kitchen that is well stocked, good air conditioning, comfortable beds and plenty of nice linens. The screened porch is perfect for watching the sun rise across the water. The grounds are absolutely beautiful. There are plenty of paddle boards and kayaks for enjoying the water right from the beach. The beach is the perfect place to enjoy cocktails in the evening breeze. When you discover Shadow Point you will not want to leave!

  • Submitted: Sep 18, 2016
  • Stayed: August 2016
  • Source: VRBO, from HomeAway
Owner's Response: So happy that you enjoyed yourself at Historic Shadow Point. Please come back soon for more experiences.
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-Stuart, FL

Heaven on Earth!

  • 5 of 5

Shadowpoint is as special as the most special places on Earth, and I feel blessed to have spent time swimming, snorkeling, cooking and dreaming making memories that will last a lifetime nestled there with people I love. Don't miss it!!!

  • Submitted: Sep 14, 2016
  • Stayed: September 2016
  • Source: VRBO, from HomeAway
Owner's Response: So happy that you enjoyed yourself and do hope you will come back soon to make more memories.
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Palm City, FL

Favorite place on the planet!!

  • 5 of 5

This fabulous 2.5 acres property is old Florida at its best! There is nothing like it in the Florida Keys or anywhere for that matter. Here you can go back in time, surrounded by water on three sides and let all your cares fall away. Whether you are a small or large group with children and/or pets, this is a safe and wonderful world for them. Memories are made here!!

Typically I love to go out to eat, but when I stay here I never want to leave the property! There is a huge family style dining table and huge porches with water views. Forget restaurants! We always cook in and savor the beauty. Of course if you do choose to go out, there are plenty of fabulous restaurants nearby.

The houses, gardens, beach and beach items are perfectly maintained. We were married here 3 years ago and just came back for our anniversary. It is a truly magical place in every way and we can't wait to go back!!

  • Submitted: Apr 28, 2016
  • Stayed: April 2016
  • Source: VRBO, from HomeAway
Owner's Response: Your Wedding was a start to a perfect relationship with Historic Shadow Point. Don't stop enjoying and relaxing with friends down here!
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John Pennekamp Coral Reef State Park
"Fun place to take guests! Nice aquariums and can rent boats."
Mrs. Mac's Kitchen
"Perfect local cuisine!"
The Fish House Encore
"Always satisfying!"
"Right across the street . Great sunsets!"
Big Chill Restaurant
Dolphins Plus
"Great for kids to ride a dolphin!"
Tower of Pizza
"Order take out Pizza and enjoy a view of your beach while eating!"
John Pennekamp Coral Reef State Park
"Fun place to take guests! Nice aquariums and can rent boats."
Dolphin Cove
Car: necessary

This 2.5 acre ocean side estate is located at the north end of Key Largo Sound at mile marker 103 just a one hour drive from Miami International Airport. It is across the highway from the Marriott Resort yet so secluded you would think you were in another world.

Other Activities: Kayaking, Canoeing, Tubing, Boating, Paddle boarding, Fishing, Swimming, Sun bathing - All of these things can be done right from the property. Right across the highway is the Marriott Resort that offers boat rentals and parasailing. Nearby you can take a snorkel and dive boat to the most beautiful reefs in the world. Stay on land and go across the Street to 'Sun Downers' Restaurant to get a view of the bay and feed the Tarpon.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Property Damage Protection $59
Pet Fee $100
Refundable damage deposit $1,500
cleaning $500 + Tax
Tax Rate 12.5%

Rent for both houses ranges from $7500 to $8500 a week plus $500 cleaning and 12.5% taxes. During holidays, high season, special dates and events the property rents for more. We only rent the cottage with the main house so you can experience total privacy. Half of the total rental is due at time of booking. Security deposit and the other half of rent are due 60 days before the first day of rental. There is an extra charge for weddings and receptions. This is a great price for what you are getting. Privacy and seclusion and a fabulous view and your own beach with use of a double kayak, 4 single kayaks, and 2 paddleboards.
Monthly rentals are negotiable depending on the season. There is a $100 charge for each person exceeding 12 but not to go over 16. Security deposit of $1500 is required. The place will not be held until a deposit of half the rental is received. E-mail for more information and more photos. Please do not inquire about anything less than four days. Fee is $100 per dog.
Homeaway and VRBO's recent decision to impose large service fees (est $300 - $400) for booking through VRBO,s and Homeaway's platform we are permitting guests to pay directly and avoid the service fees. If you'd like to book directly please send us a request along with your e-mail.Payments by check or wire will have no fee and payments by credit card will have a 2% fee. added.

I will consider renting for 4 night or more.
Rentals comply with Sec 134-1 subsection b(1) of the Monroe county code.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

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