Private Historic Waterfront Home on 2.5 acres with Dock, Garden & Beach:6BR 4BA

Florida Vacation Rentals By Owners
  • House 2 Sq. Ft.
  • Sleeps 16
  • Bedrooms 6
  • Bathrooms 4
  • Minimum Stay 4 - 7 nights
Special Offer
Discounted Price
Last Minute Special July special

Property Description

Private and stunning, the Shadow Point peninsula is surrounded by water on three sides and is nestled within a tropical native hammock with garden planters to wander between. The two homes are the oldest residentially developed properties on Key Largo. We believe you will find it to be the most charming, spectacular and intimate private property in Key Largo available as a vacation rental. With a PRIVATE BEACH, private dock, an ample yard for kids to run and play, gorgeous sunrises and sunset skies, fabulous moon rises over the water and green islands beyond, tropical gardens and delightful breezes, the character of both the property and the buildings is true old-Keys style. You couldn’t have found a better place for your enjoyable stay!

Our historic, one-of-a-kind estate offers a rare glimpse of Key Largo as it was over 100 years ago. The two guest houses offer the vacationer a chance to step back in time and experience the charm of days gone by with its historic “Conch Style” architecture and original Dade County hardwood floors and walls throughout. Because of its size and location, Shadow Point is perfect for boaters, divers, snorklers, kayakers, and birdwatchers and can comfortably accommodate family retreats, workshops, small weddings, film and modeling shoots, anniversary parties, and commitment ceremonies. It is a wonderful place for celebrations of any kind! During major Holidays and special events we only rent for 7 nights or more. There is an extra charge for those dates.

The gated 2.5-acre estate is filled with lush tropical trees and has a 180-degree view of pristine Largo Sound, located within the world-famous John Pennekamp Coral Reef State Park. Launch the kayaks and paddleboards that come with your rental or just relax and build your own sand castle. We are entirely surrounded by Largo Sound, not canals, and there are no houses across the sound from us to obstruct our view. Two deep-water mangroves cuts - one at the north and one at the south end of Largo Sound - lead to the open ocean. The Marvin D. Adams Cut is only a 1/4 mile south of the property and provides boat access to the bay side of Key Largo, its many boat-friendly restaurants and Blackwater Sound. Bring your own boat or rent one for your stay and tie up at our dock that offers 220v electric and fresh water for boats up to 40 feet. Some of the best coral reefs, dive wrecks, and fishing spots in the country are just a short ride away!

Shadow Point is a registered, gated HOA and offers an exclusive retreat for vacationers desiring an intimate and private setting. We offer intimate wedding and commitment ceremony packages, where you can use the property for all your events - not just your wedding ceremony: the property is also great for hosting out-of town guests and holding your reception as well. Sunday brunch and day-after beach parties can also be accommodated. All in one beautiful place, without moving your guests from venue to venue.

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 look for our name on the internet.

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  • Yellow Room : twin/ single (2)
  • Blue Room : twin/ single (2)
  • Sunrise Room, Private bathroom : King
  • Turquoise Room, Private Bathroom : King
  • Cottage Bedroom North : twin/ single (2)
  • Cottage Bedroom South : twin/ single (2)
  • Cottage Living Room : sleep sofa /futon
  • Baby Cribs and Cradle : baby crib (2)
  • Sleeping Porch: 2 Day beds or one hammock : twin/ single (2)
  • Turquoise Room Bathroom : toilet, shower, Shower seat and handles for guests needing a little security
  • Outdoor Shower : outdoor shower, Rinse off from the beach or boating outdoors!
  • Cottage Bath : toilet, shower, Large room shared with new laundry facilities.
  • Blue-Yellow Bath : toilet, combination tub/shower
  • Sunrise Bathroom : toilet, shower
Safety features:
  • Exterior lighting
  • Smoke detector
  • Fire extinguisher
  • First-aid kit
Location Type:
  • Beach (Your own private beach right on the property where you can swim and launch our kayaks and paddle boards.)
  • Beach View (Secluded and perfect for children, couples looking for a romantic getaway, family get-togethers, weddings or other meaningful events!)
  • Water View (The site is located within the Pennekamp Coral Reef State Park: views east, northeast and southeast are of the water and undeveloped, pristine green barrier islands, spectacular sunrises, and rainbow)
  • Near The Ocean
  • Beachfront
  • Waterfront
  • Resort
  • Ocean View
  • Guests provide their own meals
  • Telephone
  • Parking
  • Laundry Soap
  • Air Conditioning
  • Local Activities Guide
  • Local Maps
  • Internet
  • Heating
  • Linens Provided
  • Washing Machine
  • Clothes Dryer
  • Towels Provided
  • Wireless Internet
  • Iron & Board
  • Paper Towels
  • Local Restaurant Guide
  • Shampoo
  • Basic Soaps
  • Toilet Paper
  • Thermos Bottle
  • Activities Guide
  • Ceiling Fans
  • Filtered Water
  • Hair Dryer
  • Living Room
  • Parking for RV/Boat/Trailer
  • Dishwasher
  • 4 Ring Stove
  • Pantry Items
  • Refrigerator
  • Cooking Utensils
  • Freezer
  • Coffee Maker
  • Stove
  • Dishes & Utensils
  • Toaster
  • Catering Available
  • Oven
  • Microwave
  • Grill
  • Blender
  • Ice Maker
  • Lobster Pot
  • Kitchen
  • Dining Area
  • Dining
  • Comfy seating for 14 people
  • Child's Highchair
  • Television
  • Books
  • Games for Kids
  • Satellite / Cable
  • Radio
  • Stereo
  • CD Player
  • Audio Tape Player
  • DVD Player
  • Books for Adults
  • Books for Kids
  • Games
  • Music Library
  • Toys
  • Video Library
  • Lawn / Garden
  • Beach Chairs
  • Walkway to Water
  • Beach Towels
  • Deck / Patio
  • Large Cooler
  • Fish Cleaning Table
  • Barbecue
  • Child's Swing
  • Sand Box
  • Kayak / Canoe
  • Outdoor Grill
  • Boat Dock
  • Gated Community
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda
  • Screen Porch / Veranda
  • Water Sports Gear
  • Tennis
  • Low Allergen Environment
  • Long-term Renters Welcome
House Rules:
  • Check-in: 4:00 PM Check-out: 11:00 AM



Rate Period Nightly Weekend Night Weekly Monthly

Standard Rates

4 nights min stay
$1,300.00 $1,500.00 Fri,Sat $8,400.00 $25,000.00
Additional information about rental rates:
  • Cleaning Fee $ 500
  • Tax Rate 12.5%
Notes :

Note: All legal and local holidays are priced higher
$500 More If You Rent Over Holiday (Chritsmas, Labor Day, New Year, Memorial Day, Thanksgiving)

Extra $500 For Mini Lobster Season

Pet Fee : $150

Extra Person Beyond 12 Is $35/Night




Add a Review

Wytske K.

boston MA
1st February, 2019
Waterfront oasis for the whole family
This has been the third time we stayed at Shadow point - The two houses have enough space for a family gathering, with the 4 bedrooms/3 baths in the main house and the two bedrooms in the cottage. The grounds are wonderful, with many shade providing trees and with several sitting areas for people to enjoy. The house has a beautiful screened porch sitting area that allows you to enjoy the breeze off the water while still being in the comfort of a home. The kayaks are a wonderful way to explore the waters and mangroves. We have in the past rented a boat and the dock allows you to keep it there overnight. Being so close to the "cut" allows you to easily take the boat to the bay side and to the ocean. Key Largo has stores for groceries, and several wonderful restaurants, including the fish house. However, with a well stocked kitchen, we often cooked our meals at the house so that we could enjoy the grounds and view and company. Our family had a little toddler come along the last time, and he had the time of his life. We did not need to bring many items, since the house has an available crib, high chair and even a baby swing outside. The only worry was not to let him escape on his own due to the property being surrounded by water on three sides. Shadow point will always be a favorite place for us to stay.

Pamela F.

18th November, 2018
Gorgeous, private, historic, old Florida estate.
Our 4-night stay at Historic Shadow Point was the perfect destination for our annual college sorority sister trip! The private waterfront setting is serene, from sunrise to sunset. There was a continuous breeze the whole time we were there! The historic Main House, Cottage and screened porches are graced with historic and artistic decor that take you to another time and place. We spent every morning sipping coffee under the Gumbo Limbos on beautiful Largo Sound. The owner has done a stunning job providing many amenities for the pleasure of her guests: Gourmet kitchen accessories, colorful decor throughout, lovely tropical landscaping, kayaks—-I could go on and on! She was always accessible if we had a question. We appreciated her vendor list, which included Caribbean Catering for our delicious arrival dinner. We also enjoyed dining at Mile Marker 88 (sunsets, live music) Fish House (no reservations, but worth the wait!) and Sundowner’s (feed the tarpon & enjoy sunsets). If you want a delicious breakfast you must go to Mrs. Mac’s Kitchen-Bayside! (Super friendly and it’s all about what YOU want. ) Historic Shadow Point is within easy driving distance to Tamiami Trail where we enjoyed an exciting private airboat trip at Everglades Safari Park and later, hiking trails in Everglades National Park (Main Entrance). Stop by “Robert Was Here” for their famous shakes and all things Florida. Whether you have a reunion, wedding, family gathering of any kind, Historic Shadow Point will make it even more memorable for all! You will never forget it and will dream of returning! Most of all: Don’t over plan, enjoy this special place.

Lee Ann W.

17th June, 2017
A Special Gathering Place
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!!

Roxanne F.

Pompano Beach, Florida
12th May, 2017
Never wanted to leave!
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!

20th November, 2016
Best of the Keys!
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!

15th September, 2016
Heaven on Earth!
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!!!

Elsie S.

18th September, 2016
Florida at its best!
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!

Deb R.

28th April, 2016
Favorite place on the planet!!
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!!

Alan R.

New York
27th May, 2016
Three generations of our family enjoyed this wonderful property the week of March 19-26th. It was perfect. The property offers spectacular views in each direction. The vegetation and unique trees offer many photo ops. With the gentle slope of the beach, we never had to worry about the little ones playing in the water. With the many kayaks and stand up paddles, there was always something to do. Wake up early, and you will be treated to a beautiful sunrise. Go across the road to the Marriott and you will see magnificent sunsets with happy hour offerings. On a cloudy day, we took the kids to Theater by the Sea, which was well worth it. The house was well stocked and if you choose to cook, you will find all the utensils, pots, pans and serving dishes you can imagine. Every nook presents part of the collectibles gathered over the years of ownership. There were board games for both young and old. All your needs are met, with ample supply of towels for both personal and beach.


Homestead, FL
3rd January, 2016
Best property in Key Largo!
My family and I have rented this property over the holidays twice now and will definitely continue to do so as long as it's available to rent!! It's the best property in Key Largo with great historic value and natural vegetation providing a private waterfront experience. We always love playing on the beach with the little ones and have really enjoyed the kayaks and paddleboards available on the property as well. We bring our boat down and dock it right on the property, and its location on Largo Sound next to Adams Cut allows for easy access anywhere in Key Largo by water. It's gorgeous inside and out, and we always look forward to our visit here!

Carolyn S

Fort Pierce, FL
20th December, 2015
Piece of Paradise
Shared a unique experience meeting group of old friends for taste of old Florida Keys. Great ambiance with large, well-stocked kitchen and charming dining room, several living rooms and spacious porches. I stayed in the smaller cottage and loved the authentic decor, comfy bed with crisp linens and fluffy towels. The view from every room made me feel as if I had truly stepped back in time and was far away. In truth it was just minutes from US 1 and all the local markets and restaurants. Weather did not permit me to experience the kayaks and paddleboards this time. Definitely will return for another visit.

Tracey W.

Fort Lauderdale, F
20th November, 2015
Enchanting wedding venue
My wife and I chose to hold our wedding at Historic Shadow Point and it was the best decision ever. After months of planning and much anticipation, the guests arrived and just as impressed as we were when we first visited and decided on the venue. The scenic views and beautiful trees served as the perfect setting. The houses were beautifully decorated and inviting and the kayaks were fun to use for winding down and enjoying the wildlife. The owners are warm and welcoming. We will definitely return.
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