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Shadow Point-7 Day Min

Bedrooms: 6

Bathrooms: 4 full, 1 ½-bath

Sleeps: 14

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Overview ↑↓

Escape to Historic Shadow Point, a one of a kind waterfront estate and gardens located on 2.5 acres along Largo Sound in Key Largo. This secluded Florida Keys retreat is nestled within a tropical native hammock with a private beach, private dock, direct water access, an ample yard for kids to run and play, watersports, gorgeous sunrises, and unmatched privacy. Enjoy the space and comfort of two homes, the main house and cottage, which are the oldest residentially developed properties in Key Largo. These accommodations offer all the charm of Old Key Largo but with modern conveniences. You couldn’t have found a better place to experience the Florida Keys!

The Main House features four spacious bedrooms, including one king bedroom with private bath, and three bedrooms with twin beds. The cottage offers two additional twin bedrooms, a stocked kitchen, laundry facilities and a living room with a twin trundle for additional sleeping space. Both homes feature gorgeous screened-in porches, local artwork, air conditioning, WI-Fi and comfortable living areas.

Outdoors is where Shadow Point truly shines. Enjoy the property's sandy beach, docks and expansive views of Largo Sound. Kayaks, paddleboards, snorkeling equipment, life jackets and floating tubes are provided for your use. Swim, snorkel, paddle or simply relax among the tropical gardens and waterfront gathering areas. Boaters can enjoy dockage with fresh water and electric service. The property also features gas grills, outdoor dining areas and plenty of room to unwind by the water.

Our historic, one-of-a-kind estate offers a rare glimpse of Key Largo as it was over 100 years ago. This property allows you 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. 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 bayside 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.

Amenities ↑↓

Additional Bedding 3

Twin

Additional Bedding 4

Twin

Area

Key Largo

Bay View

Yes

BBQ

Gas

Bed Type 1

King

Bed Type 2

King

Bed Type 3

Twin

Bed Type 4

Twin

Bed Type 5

Sleeper Chair (Twin)

Bedroom 1 Level

First

Bedroom 2 Level

First

Bedroom 3 Level

First

Bedrooms

6.00

Boat Access

Seawall

Boat Dockage

Yes

Cable TV

Yes

Coffee Machine

Yes

Coffee Machine Type

Drip and keurig

Dishwasher

Yes

Floors

1 story

High Speed Internet

Yes

Max Boat Length

35'

Microwave

Yes

Number of Bathrooms

4.5

Oven

Yes

Property type

Single Family Home

Refrigerator

Yes

Sleep Cap

Smart TV

Yes

Stove

Yes

Toaster

Yes

VRBO Listing ID

5500111

Washer and Dryer

Yes

Waterfront

Yes

Weekly Rentals

Yes

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Reviews ↑↓

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Review

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Fantastic

Review Date: October 8, 2026

Vacation Date: April 25, 2026

"This property was fantastic. The grounds were beautiful and to house supplied with absolutely everything we would need. We housed and fed 14-16 people comfortably during a Family Celebration of Life. Management was responsive with a plumbing issue.

Reviewed By: Denise MONTISANO

We LOVE Shadow Point

Review Date: October 8, 2026

Vacation Date: January 14, 2024

"My family and I had another amazing stay at Shadow Point! This property is so unique - it feels like you are on a private island. A very peaceful and relaxing place --- and, with so much history and nature! There is something for everyone, and all that you need is onsite. We spent the days on the water, or on the beach...and nights around the huge kitchen table at the main house - there was plenty of room for all 14 of us. Marlee, the property manager/owner is always hospitable and responsive. Shadow Point has a special place in our hearts - we have so many great memories and we look forward to making more. We can't wait until next time!

Reviewed By: Kristen Potente

Holiday in the Keys

Review Date: October 8, 2026

Vacation Date: December 19, 2023

"Historic with interesting art, antiques, and photos throughout. Very comfortable and fit our 12 adults easily. All in working order with lots of recreation available inside and out. Thank you for making Christmas 2023 so memorable.

Reviewed By: Donna Cooper

Paradise!

Review Date: October 8, 2026

Vacation Date: June 24, 2023

"For someone who loves a property with history, charm, and character around every corner, this house has it all. We brought our three sons and several of their friends, and the setup with the guest cottage for the boys was ideal. Morning coffee overlooking the water was my favorite time of day. The kayaks and paddle boards in the shed were awesome, and there was always something for the kids to do. Host was easy to reach and the house had everything. Kitchen was stocked with everything you could need. Completely recommend!

Reviewed By: Kathleen Murphy

Perfection

Review Date: October 8, 2026

Vacation Date: April 1, 2023

"Ideal property and exactly what would be expected for “Keys” island feel. Very private.

Reviewed By: Jack Cowan

Beautiful setting, under the statuesque trees, with glorious views

Review Date: October 8, 2026

Vacation Date: February 18, 2023

"This special part of Key Largo history is full of the memories of generations. The two charming houses are full of art and interesting collections from the past. The tranquil property, with peaceful breezes, is a haven from the modern Key Largo.

Reviewed By: Virginia McIntyre

Beautiful

Review Date: October 8, 2026

Vacation Date: February 13, 2023

"An amazing property. Great little beach for grandkids and plenty of room for 12 of us.

Reviewed By: Jeff Marqusee

Another Wonderful Stay at Shadow Point

Review Date: October 8, 2026

Vacation Date: December 26, 2022

"We had another amazing stay at Historic Shadow Point! Everything you need for a relaxing vacation is onsite at this private and peaceful retreat....though we did venture out for some deep sea fishing and a walk on the 7-Mile Bridge, we mostly spent the days relaxing on the beach, looking for sea life, fishing, paddling, grilling, sipping cocktails, and enjoying the salt life. There is something for everyone - we had a group of family ranging from 4-76 and a couple of pups, and we all LOVE making memories at Shadow Point. Marlee, the property manager/owner is so hospitable and responsive. Counting down the days until our next stay...!

Reviewed By: Kristen Potente

Fun for all!

Review Date: October 8, 2026

Vacation Date: December 24, 2022

"We loved the house and cottage! They fit our family perfectly, but our favorite part of this property was the beaches, hammocks, spectacular views and quiet alcoves! Even had visits from a manatee!

Reviewed By: Nancy S

Family and friend’s vacation

Review Date: October 8, 2026

Vacation Date: July 9, 2022

"This is probably the nicest vacation rental property we have ever stayed at. The privacy and amenities were amazing and 180 degree access to the water and water views. Great location, very easy drive to the Miami airport and exploring the keys. Simply magical

Reviewed By: Mary Nicklin

Awesome Awesome Awesome

Review Date: October 8, 2026

Vacation Date: June 13, 2022

"It's Amazing. It's where old Florida meets modern convenience. The Sunrises and Sunsets are fantastic, Everything you need is there. Appliances, Cookware,Everything. There were Sixteen of us in our Family. Plenty of room and very comfortable. Our Nine year olds fished all day every day and most of the nights. We watched Dolphin swim by in the early evenings. We Kayaked every day. And mostly we just hung out. It was awesome.

Reviewed By: Donald Plourde

Shadow Point

Review Date: October 8, 2026

Vacation Date: April 21, 2022

"Nice, relaxing place to stay.

Reviewed By: Todd McDowell

Relaxing and beautiful

Review Date: October 8, 2026

Vacation Date: March 3, 2022

"We had a great time at the property. It is in a terrific location, lots of history featured for us to learn and enjoy, and the gardens are amazing. Lots of hammock time! The property managers were so helpful and easy to communicate with, but we really didn’t need much - the house was well equipped and comfortable.

Reviewed By: Jennifer Sikora

Great Reunion

Review Date: October 8, 2026

Vacation Date: July 24, 2021

"Ideal property for family reunions. We were a party of 14; 2 grandparents, 5 adults and 7 grandchildren. Kids loved fishing off the dock and kayaking. Adults enjoyed evening “sundowners”. Dolphin Experience was a treat as was discover scuba and shallow dive. Everyone enjoyed a day on the water in a 24 ft deck boat. Not a dull moment but plenty of time to relax and enjoys the beautiful gardens surrounding the house and cottage.

Reviewed By: William Butler

Historic Shadow Point

Review Date: October 8, 2026

Vacation Date: March 29, 2021

"Amazing property with beautiful gardens

Reviewed By: Virginia Hall

Great Unique Stay!

Review Date: October 8, 2026

Vacation Date: February 26, 2020

"Our family of 12 very much enjoyed our stay at historic shadow point! When booking a property with so much history, it is understood that you are going to encounter some aspects of the property that could use some touching up. This home is all about the outside! The landscaping, hammocks, kayaks, beach and swings make for a fun day outside. The two homes are dated and have their pros and cons. We had an issue with the shower heads and the owner responded instantly with a phone call and sent a plumber the next day! Overall, this property is truly a home with lots of character and it shows how much love and care has been put into it over the years. If you are ok with that type of home this is a perfect home for you! If your looking for perfectly sparkling floors, a central air system and squeak free floor boards this may not be your cup of tea. Thank you for a great stay shadow point!

Reviewed By: Tyler Butler

Wonderful Family Gathering

Review Date: October 8, 2026

Vacation Date: February 16, 2020

"The rooms in main house and cottage were perfect for our group. The grounds are spacious with various settings. Hard to do them justice with just words. Property manager was quick to respond to any questions After month of searching for gathering spot, we all agree we made the best choice.

Reviewed By: Robert Pincus

Absolutely charming, beautiful and quiet

Review Date: October 8, 2026

Vacation Date: July 19, 2019

"We couldn’t have asked for more. The accommodations were superb. The landscape was pristine and the amenities were more than enough. We celebrated my sister’s 80 th birthday and this was just the perfect place.

Reviewed By: Leni Kunick

Wonderful property!

Review Date: October 8, 2026

Vacation Date: July 16, 2019

"We had a lovely one week stay at Shadow Point and enjoyed the House, the wonderful rooms and the beautiful garden. We were a party of ten-two families of five-and it was a great place for all. A very welcoming atmosphere all around:)

Reviewed By: Kristin Sorenson

Family Gathering

Review Date: October 8, 2026

Vacation Date: May 16, 2019

"Historic Shadow Point is the perfect place for a family gathering that appreciates nature. As a native Floridian, this was truly a gem. It's a step back in time. Peaceful. Private. Florida as it used to be. The breezes were beautiful and filled the house with fresh air. This is a place to unwind, play cards, chat on the porches, kitesurf, fish, read, and be reminded of a simpler time.

Reviewed By: Caroline Bass