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

16 person family vacation, the kids 9-15 loved the beach and the docks for swimming, the kayaks were used by all. the large dining room was great for all to sit, eat and talk. Kitchen was large enough for several people to work at the same time. The historic ambiance was enjoyed by all. Close to shopping and plenty of shade trees, gorgeous location.

The pictures of this house were beautiful online and we could tell that this would be a nice place to vacation. When we arrived and toured the house and the grounds a feeling of serenity came over us and we felt completely one with nature. The grounds were well kept and beautifully landscaped. We had a 27 foot boat that fit perfectly on the dock. The property even has a mini beach for the kids to play. The house has a large kitchen and was well equipped with any and all cooking supplies. We even used their waffle maker for breakfast a few times. The beds were comfortable and there was a constant breeze flowing threw the house with the windows open and a/C off. We used the a/c at night to sleep. The house has so much character and a nostalgic keys look and feel . We are so lucky to have come across this treasured property and can't wait until we return!

11 Directors of a large Medical Device company spent a week on this amazing property. We rented a massive 34 foot boat and docked it at the house the entire week. The property owners and the care taker were VERY easy to work with and the communication was spectacular. They are very used to hosting people and have every single thing you could think of there for you. This is classic old world Key Largo charm. We had meetings on the wonderful grounds outside and also in the living room with the cool breezes blowing through the windows. All rooms have wall AC that provide unbelievable A/C when/if needed. The towels and sheets were in A++, and the kayaks, paddle boards were excellent. The best part is how secluded you feel surrounded on 3 sides by water, but anytime we needed supplies or wanted to go out to eat, everything was within a 2 minute drive or a short walk. For those boat/water lovers, this is a perfect location. It is literally right next to the cut that goes to the Gulf side, so if it gets windy, just head of there for the day. However, the best was the access to the Ocean and all the best dive and snorkling sites that are very very close to the house. We had people who had vacationed their entire adult life on Key Largo and they all said this house was the best location they have ever stayed in for location on the water. We had female and male attendees and this property was set up perfectly with 2 homes on the property. In the cottage we had 4 females and they had their own bathroom and kitchen and living area (pull out bed could have slept more if needed). The males stayed in the house and there was plenty of rooms and bathrooms as well. I can't rave enough about this property!!! Absolutely book with zero concerns!

This property is one of a kind. Nearly every window in the house and the cottage has a view of the water. It is very secluded and private with plenty of room for a big group. We had two boats docked up and it was so easy just to launch the boats into the water right from the house instead of having to go to a nearby boat ramp and pay to use the ramp. We also liked how easy it was to get out to the ocean to catch lobster and fish. We ended up with 29 lobster, a grouper, a hogfish, and a mutton snapper. We absolutely feasted like royalty and the kitchen made it easy to do that. It was fully stocked with spices and every cooking utensil/pot/pan etc that you could ever need. We loved ringing the bell outside when a meal was ready, we called it the dinner bell! There is no shortage of entertainment here from the paddle boards and kayaks to the old school poker table that we used almost every night. Between the group we had three small dogs and they enjoyed it as much as the people. Shadow Point is a special place and we had a blast! I highly recommend it.

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.

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.

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!

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. I would not hesitate to return and have recommended this home to others already.

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!!

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!

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!!!

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!

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!

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!!

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.

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.