Islamorada water front with free boat tie-up. Available weekly, Saturday to Saturday

Florida Vacation Rentals By Owners
  • Condo
  • Sleeps 4
  • Bedrooms 1
  • Bathrooms 2
  • Minimum Stay 7

Property Description

The Osprey Nest (MM 82.3) is a private condo residence which is wonderfully maintained. It is operated under FL DBPR license # MOT 5403060 and is inspected annually. This Non-Smoking home is professionally cleaned prior to your arrival. The sleeping accommodations are in queen beds. The second sleeping area is a Murphy bed in an alcove off the living area. All appliances are relatively new and in excellent condition. The air conditioning system is a 'split' system and is very quiet (like central air/condx). The floors are all porcelain tiled. The home is light, bright, and airy. Free secured private WIFI for guests use.

In addition to the actual residence, there is a large deck terrace ( approx. 1200 square feet) adjacent to the master suite with patio furnishings and a gas grill for your private use. There are super views from this deck. In addition to the home you have the use of the boat basin and jetty. You are allowed to dock one boat up to 26 feet in length. There is water and electricity to the tie-ups.

It is private and secluded with private homes on either side of the property. The actual location is close to both the ocean as well as back-country fishing.

Don't miss checking the Osprey Nest website and the Virtual tour, linked below.

Unique Benefits

Excellent snorkeling and swimming from the jetty. Sunsets are spectacular. Good fishing from the jetty.

Why Kids Love It

They love viewing all the wild life in the water at night. Bring a flash light.

Area Information

Islamorada is well known as the heart of the sport fishing in the Keys. The Village of Islamorada is composed of 5 separate Islands all with their own atmosphere. Founder's Park (MM87) on PLantation Key is special . The Osprey Nest is located on Upper Matecumbe Key which is the Crown Jewel of them all.

Attractions Within Walking Distance

The Lorelei bar and grill (MM81.2) is quite a place. They also call it "City Hall" as all the locals hang out here. They often have live music and are located outside right on/in the water.

Favorite Places To Eat

Lazy Days (MM 79.8). Try the Hog Fish!
Marker 88 (MM88)
Shrimp Shack(81.9)
Mangrove Mike's(MM82) (Breakfast & Lunch)
The Hungry Tarpon (MM77.5) (Breakfast & Lunch)
Island Grill(MM88.5)
Pierre's (MM81.5) (high end)
Morada Bay(MM81.5)
The Green Turtle(81.2)
Lorelei Bar & Grill(MM81.2) (Favorite watering hole)
Bayside Gourmet(82.5)

Inside Scoop

City Hall Restaurant (MM88.5) near the Monroe County offices on Plantation Key is a small boutique dining establishment . They have very well prepared, moderately priced entrees all served by the owners.

Sunrise Market (MM91.8) in Tavernier (Ocean Side) is a small Cuban specialty market. They have very good rotisserie chicken, fresh baked Cuban bread, and many side dishes. I had them do a Turkey for me once....a real treat!

Moose Lodge of Islamorada (MM81.5) is available to members. They have low priced drinks, food and conversation with locals

Show More

  • Air Conditioning
  • Full Kitchen
  • No Pets Allowed
  • Parking
  • Balcony
  • Heating
  • Non-Smoking
  • Towels Provided
  • Deck / Patio
  • Internet
  • Ocean View
  • Water View
  • Dock / Boat Slip
  • Linens Provided
  • Oceanfront
  • Waterfront
  • Free WiFi
  • Managed by Owner
  • Outdoor Shower
  • Wireless Internet
  • Blender
  • Dishwasher
  • Microwave
  • Stove
  • Cable / Satellite TV
  • DVD Player
  • Outdoor Grill
  • Television
  • Ceiling Fans
  • Freezer
  • Oven
  • Toaster
  • Coffee Maker
  • Hair Dryer
  • Refrigerator
  • Washer / Dryer
  • Dishes & Utensils
  • Iron & Board
  • Kayaks Onsite
  • Bicycle Rental



Rate Period Nightly Weekend Night Weekly Monthly

14th April, 2021 to 18th August, 2022

7 nights min stay
$240.00 - $1,295.00 -

18th August, 2022 to 22nd December, 2022

7 nights min stay
$240.00 - $1,195.00 -

22nd December, 2022 to 20th April, 2023

7 nights min stay
$240.00 - $1,395.00 -
Additional information about rental rates:


Add a Review
Vacation Rentals by Owner

Susan Weidknecht

Old Hickory, TN
30th April, 2018
Aweseome Condo
This condo has such a great location and beautiful views. We walked to a few restaurants & drove short distances to others we love. It was also great being able to just cross the street to spend time at the Islamorada Beer Company! The condo itself has a great layout & is well stocked. The beds are so comfortable & the 2 baths are very nice. It's a pleasure dealing with Don, too! Everything was so wonderful that we've already booked for a week this December.
Vacation Rentals by Owner

Ed And Wendy De Vries

Stuart, Florida
30th April, 2018
The perfect nesting place in paradise!
The Osprey Nest is a very quiet, tropical nesting place that we have rented multiple times over the past 10 years. It is a 2nd floor condo that is very well equipped, comfortable and has most everything you need for a week’s stay. The inside is clean and modernized. The Bay, lagoon and sunset views from the main living area are truly amazing! It is located within walking distance of many local favorite eateries and yes, even a local brewery. The entire apartment complex consists of multiple small dwellings and is fashioned after an old keys style fish camp. The grounds are beautiful! The whole property is very tropical looking with several palm trees and flowering foliage. The Osprey Nest also has a huge deck that overlooks the back yard, boat lagoon and Florida Bay. There are chairs there as well as a barbecue and table for dining outdoors. The lagoon is deep and wide enough for my 21ft boat and there are fish cleaning tables and fresh water hoses available. Don is a pleasure to do business with and makes the whole rental experience a breeze! Looking forward to returning again soon! We LOVE this place!Stuart Ed and Wendy
Vacation Rentals by Owner

Kathy And Gary Melvin

Reidsville, NC
2nd May, 2018
An Islamorada hideaway
We have visited the Osprey Nest for over 10 years now! It is a beautiful place, both the living space and the property overall. Don works to keep the apartment/condo updated with nice furnishings and appliances. The view is wonderful, both the living area and the master bedroom have water views of the lovely Florida Bay. We like to cook while there and the kitchen has everything you need. Together with the gas grill on the deck we have enjoyed great meals. As others have mentioned, there are wonderful restaurants within walking distance or a short drive, we love the walk to the Loralei for outside dining, views, and music! The jetty at the boat basin is built up on a coral base, has a couple of palm trees for shade, and a fantastic place to sit and read, watch the boats go by, and see the most amazing sunsets. We have loved having our boat with us the past couple of years, just to hop in and explore the area along with great fishing. Key West is about an hour and a half away on a cool sightseeing drive if you are so inclined to become "Key Wasted", but at the Osprey we usually become afflicted with Keys Disease, which is not wanting to drive more than 5 miles in any direction, it is all right there for you!!
Vacation Rentals by Owner

Eve Hudgins

Phoenix, AZ
13th May, 2018
Osprey Nest, the perfect Florida Keys vacation rental
Perfect Florida Keys rental… every time I’ve had the pleasure of enjoying this property it’s been everything I could possibly expect. Clean, lovely and comfortable furnishings, fully, and I mean fully equipped, steps from the water and those spectacular Florida sunsets with the very best view available from the expansive deck or the convenient jetty… you pick! I don’t think there’s a better view available. Great restaurants and bars in easy proximity if you don’t feel like whipping up a meal in the condo or grilling a fish, or 10, on the deck. Don, the owner, is exceptionally responsive and will bend over backward to ensure you have the best vacation ever… and keep coming back… just like I have!
Vacation Rentals by Owner

Chuck Steele

Greenwood, South Carolina
16th May, 2018
Fun Times in the Keys
The Nest is in a great location on the bay side , spectacular sun set view. Condo is well cared for and has all the features of home. My wife and I enjoyed our stay to stay immensely. Great place to moor a boat and only steps from your door (included in the condo rental). I rented a boat and fished in the bay. Tarpon fishing was outstanding!!!!! Clilled on the pier in the early evening with the other guest sharing fishing stories and a cold beverage or two. Don is the best, communication is fast and easy. Don looks out for is guest. We are returning in two weeks for you second stay at the Nest!!!!
Vacation Rentals by Owner

Tony Bracci

St. Petersburg, Florida
19th May, 2018
Best weekly rental in Islamorada!
I've stayed at the Osprey Nest numerous times and will be there for my I believe my 5th time this summer 2018. The "Nest" is located on a beautiful, tropical property and is meticulously maintained. My favorite feature of the lot itself is the protected basin to safely tie-up your boat, clean fish and mingle with the other visitors...which are mostly repeat customers that you get to know over time. Inside the Nest you want for nothing, it has everything that you're used to at your own home, all of the electronics and appliances work as they should, linens are clean, bathrooms and the rest of the place are immaculate. The Nest has a private deck for laying out in the sun then grilling your fish for dinner, the sunset views are absolutely unforgettable. Stop clicking and book the Osprey Nest, you'll be glad that you did!
Vacation Rentals by Owner

Mike Boland

Washington DC
29th May, 2018
Great Place!
My wife and I stayed in February 2017 and we are going back. Need I say more? Great place, beautiful setting, excellent location, wonderful fishing, … the perfect vacation.
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