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671 sq. ft. The "Nest" villa (one of 7 privately owned condo residences) sits on a 1 acre lot located on Islamorda's beautiful Florida Bay. Stunning water views and unforgettable sunsets are guarenteed. The property is filled with mature tropical landscaping along a tree lined private gravel driveway and the entire property is truely a hidden gem.
We are sufficiently off the beaten path yet very well located and within easy walking distance to a number of great shops (including a bait & tackle center), bars, cafes and restaurants. A great local brewery the "Islamorada Brewery & Distillery" with beer garden and food truck is conveniently located directly across the street.
Don't miss checking our official "Nest" website: TheKeysNestVilla. com
THE VILLA
The fully air conditioned villa is very light, bright and airy with wonderful water views from most rooms. Wood Plantation shutters provide privacy when needed.
The Master bedroom consists of a King size bed and on-suite bathroom with large vanity and walk in shower (complimentary soaps & lotions provided). The room has its own entry door leading directly to the private roof top terrace. Lots of closet storage. Flat screen smart TV. Ceiling fan. Bath robes and beach towels provided.
The living room is bright and spacious with a comfortable leather couch, Dining table and chairs, Flat screen TV and stereo receiver. The second sleeping area is a queen Murphy bed annexed in an alcove off the main living area. Adjacent to the living room is a second private bathroom with walk in shower and vanity plus full size laundry. A portable screen is available to provide extra privacy for guests sleeping in the Murphy Bed.
A functional and recently updated kitchen with breakfast bar is equipped with modern appliances and open concept shelving making it easy to find just what you want when you need it! The fridge/ freezer has an ice maker*. There is a stove, toaster oven and two coffee makers (Keurig and drip filter) plus a hot pot & blender. Dinnerware and utensils are available for up to 6 persons.
Free WI-FI & high speed internet is available for guests use.
This is a Non-Smoking home and is professionally cleaned prior to your arrival.
ROOF TERRACE
In addition to the actual residence, there is a large private roof top sun terrace, (approx. 1200 square feet) with comfortable loungers, patio table and chairs and also a gas grill for your use. A shade sail and patio umbrella provide adequate shade from the sun as needed. A refreshing outdoor shower is also available. There are beautiful marina and water views from this deck.
BOAT DOCK
If you bring your boat, you have free use of the boat ramp (we suggest boats up to 18 ft. use the ramp), marina dockage and free on-site trailer parking. You are allowed to dock one boat up to 26 feet in length. If your boat is too big to launch at our ramp there are several public access ramps nearby (Angler House Marina highly recommended). There is water and electricity adjacent to the tie-ups.
Please note rentals are typically 7 nights minimum (Saturday to Saturday) during the high season. Longer term rentals are welcome.
The property is operated under FL DBPR license # MOT 5403060 and is inspected annually by the state of Florida.
Registration Number: 5403060
Unique Benefits
This is the perfect spot for your next Keys fishing, paddling or diving adventure or simply an ideal place to just kick back, relax and unwind while enjoying the peace, tranquility and stunning water views.
The entire property is very private and secluded with waterfront homes on either side of the property.
Safe and secure boat dockage with well lit harbor. Free on site boat trailer parking. Dockside water and electric.
Easy access by boat to the ocean directly from Florida Bay via Whale Harbor channel or Tea Table Key channel. The actual location is close to both the ocean as well as back-country fishing.
Bicycle, kayak and paddle board rentals are available at "Back-Country Outfitters" located directly at the end of the driveway!
Walking distance to some great bars and restaurants. If if you prefer use the "freebee" eco friendly free shuttle to get around town.
"Founder's Park" (MM87) behind the Visitors Center on Plantation Key is special and well worth a visit. It has a beach, dog park, Olympic Pool, Marina & boat ramp (free entry with your rental contract).
Spectacular water views and sunsets guaranteed.......the best in the Keys!
Why Kids Love It
Excellent fishing from the jetty
Swimming and Snorkeling directly from the boat ramp area or use the swim ladder on the jetty
Kayak and Paddle Boarding directly from the shore
Enjoy watching all the abundant sea-life in the water at night. Bring a flash light!
Close to Founders Park & Beach
The Village of Islamorada is composed of 5 separate Islands all with their own unique qualities. The "Nest" villa is centrally located on "Upper Matecumbe Key" which is the Crown Jewel of them all.
Islamorada is well known as the heart of the sport fishing in the Keys and is also known as the Fishing Capital of the World.
In addition to the great and varied fishing, the Island is also a great location for many other water sports including snorkling, diving, kayaking, Stand-Up Paddle Boarding, Kite Surfing and Wind Surfing.
The world famous party and gathering spot, the "Islamorada Sandbar" is just a short distance off-shore by boat. Numerous charters offer private sandbar and snorkle tours.
The Alligator Reef Lighthouse is a must see destination just 5 miles off shore.
Feed the Tarpon at Robbies Marina is a must do!
The Islamorada Beer Company Brewery
Bitton's French Cafe
Bayside Gourmet Bistro
The Lorelei Bar and Grill (MM81.2)
Ocean Gardens nautical emporium
The Whistle Stop Pub & Pizza
Bayside Gourmet (MM82.5 a five minute walk)
Lorelei Bar & Grill(MM81.2 a ten minute walk)
Lazy Days (MM 79.8). Try the Hog Fish sandwich!
The Twisted Shrimp(MM87.7)
Marker 88 (MM88)
Ziggie Mad Dogs (high end steak house) (MM83)
Shrimp Shack(MM81.9)
Mangrove Mike's(MM82) (Breakfast & Lunch)
The Hungry Tarpon (MM77.5) (Breakfast & Lunch)
Chow Hound - Pizzeria (MM84 in front of the Post Card Inn)
Pierre's (MM81.5) (high end)
Morada Bay(MM81.5)
The Green Turtle(81.2)
Islamorada Beer Company Brewery (just across the street)
Bitton's French Cafe (just across the street)
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.
Moose Lodge of Islamorada (MM81.5) is available to members. They have low priced drinks, food and conversation with locals
For a great locals bar experience check out the beach bar at the "Ocean View Inn and Sports Pub"
Boat launching ramp
Boat Trailer Storage
Protected marina with electric and water
Kayak, Paddle Board and Bike rental available at the end of the private driveway
Fish cleaning station
Fish & Bait stations on jetty
Swim and snorkle from the shore or jetty
Kayak launching ramp
Paddle Board launching ramp
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Jan 01 - Aug 30 2025 | $325 | 7 nights | |||
Jul 26 - Aug 02 2025 | $400 | $2,800 | 7 nights | ||
Aug 30 - Dec 31 2025 | $325 | 7 nights | |||
Aug 31 - Dec 31 2025 | $325 | $2,275 | 7 nights | ||
Jan 01 2026 - Jan 01 2027 | $325 | $2,275 | 3 nights |
Fees:
Notes:
Change over Day : Saturday. Rented Saturday to Saturday.
No additional booking or "Resort" fees. Free parking, boat tie-ups and boat trailer parking. Free Wi-Fi
The owner will prepare a rental agreement and forward it via an e-mail attachment to the prospective guest for approval. A rent deposit of $500.00 per week is required to reserve the booking. The balance of the rent is due 60 days prior to occupancy.
Cancellation Policy: A full refund of guest funds held by owner if written cancellation is received by owner 60 or more days prior to occupancy date or if property is re-booked.
Consider vacation insurance. Go on-line to companies such as CSA Travel Protection or AIG Travel Guard. There are many options.
Last updated on May 03, 2025
Member since 2017
Speaks: English
"Holiday House" Resort Condominiums are licensed by the State of Florida Department of Business and Professional Regulation #MOT 5403060. They are inspected annually by the department. The project has a fire safety inspection annually.
The "Nest" villa, HHRCA , Inc. #3 is operating under Monroe County Tourist Development Tax Certificate and Business license #5088409 as well as with Florida Department of Revenue .
The Holiday house property suffered only minor tree limb and leaf damage. No damage to any building. Most restaurants were back open within a couple of weeks. Surge damage was primarily to the Ocean Side of the Island and we are on the bay side where no surge was experienced.
We supply most paper products, many spices, soaps and all linens. There are several sources for food items. They include The Trading Post, CVS Drugs (limited food items) and a Publix Supermarket (MM 83.2) opened May 24, 2018. We provide both a Keurig & MR. Coffee appliances.
There are several boat rental companies available nearby and lots of great private charter boats Captains ......contact us for some great recommendations
There is an "outfitters" store at the entrance to our driveway. They will deliver directly to the villa.
Audra B.Amazing location, view, and super clean!
My 18 yr old son and I stayed here at the end of September and it was a fantastic trip!We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen! It is modern and very nicely decorated. The owners thought of everything. Everything we needed was there already.There is a huge outside seating area. The view was stellar. We fished everyday and caught various fish including a barracuda. The owner was responsive to every email. She was also very kind and mailed me back a special picture we left.The only thing to note that could be missed (but IS stated in the listing) is that the murphy bed is in the living room. There is not a separate second bedroom. However, there is a separate second bathroom for the people sleeping in the murphy bed. The washer and dryer is located in that restroom.Overall, I would highly recommend staying here. The unit and view were beautiful. We will definitely be back!
Stayed: October 2024 Submitted: October 07, 2024
Brian H.paradise package, bring your boat!
clean, up to date , and stocked up for guests. your own personal marina, and sunsets to die for! trimming trees would be my only advice .view of water ( Bay) blocked by tree line... loved staying there ,great week of rest and relaxation.
Stayed: September 2023 Submitted: October 08, 2023
Mike H.A hidden jewel indeed
If i could have it for a month, i would be there,,, ,dont need any other place. This place is paradise by the bay,,,beautiful sunsets an accomodations. Ill be back.
Stayed: January 2022 Submitted: January 17, 2022
Host response
"Thank you so much Mike... there really is something special about the nest villa. We are glad you enjoyed yourself and we look forward to your next visit. Kristine"
Charlene H.More than a gem
The home was exactly as described but better. Every detail was attended to including instructions on how to use everything right down to the remote controls. Exceptional use of space with comfortable seating and bedding. Immaculate baths and kitchen which was fully equipped with everything you need. Paper items and dish soap. Spices and seasonings. Laundry soap for the full size washer dryer. Every detail attended to. Moving outdoors provided exceptional views and much used space on the rooftop terrace. Cannot recommend it highly enough. It was perfect.
Stayed: December 2019 Submitted: January 02, 2020
Host response
"So glad you enjoyed your stay at the "Nest" and found everything to your liking. Come back and visit again!"
Kathy M.Fabulous Stay!!!
What an amazing +week at this small property on Islamorada gulf side. The Nest is a 1 bedroom (+ a Murphy bed) upstairs unit in a building with 2 other units below. Large outdoor space with covered lounge space plus table and umbrella. Great view of the boat basin and the gulf. The outdoor spaces on this property (yes each of the units had a patio area with tables and chairs) create an atmosphere where all of the guests and owners socialize at the end of the day .... watching the amazing gulf sunsets. (telling fish tales.). (small surprise; we watched a manatee calf have her baby in the boat basin....she and baby visited us each day!)The unit itself was well appointed. Queen size bed in the master bedroom...2 full baths....full washer/dryer...dishwasher...microwave...stainless refrigerator...full stove...Kuerig...Literally everything we needed. Appreciated the decor .... its not just a rental; this is someone's home and it showed in all of the details.Thanks so much to Kristine and Gary for providing the perfect spot for out 1st anniversary. We will return!
Stayed: October 2019 Submitted: October 06, 2019
Host response
"Thank you for such a lovely review. We were happy to be a part of your first anniversary and look forward to be a part of more great memories. Its fantastic that you had that rare opportunity see a manatee have her baby. I hope you took a few pictures and if you did it would be great if you could post them on our "Nest" facebook page"
Mike B.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.
Stayed: February 2017 Submitted: May 29, 2018
Host response
"It is great when a guest returns! This couple is extending their stay in 2019! Glad I had the time available to accommodate them."
Tony B.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!
Stayed: August 2016 Submitted: May 19, 2018
Host response
"Tony is a long time guest as he mentions. He'll be surprised this year with the new shower in the guest bath, new washer/dryer and private Wifi system. From his review you can tell he really enjoys my retreat. That's great!"
Chuck S.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!!!!
Stayed: June 2017 Submitted: May 16, 2018
Host response
"Chuck and his Bride are one of my guests that come back each year. They enjoy and know how to make their holidays the best possible. I am blessed to have so many folks that care about my property."
Eve H.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!
Stayed: September 2017 Submitted: May 13, 2018
Kathy and Gary M.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!!
Stayed: March 2018 Submitted: May 02, 2018
Host response
"Gary and Kathy are one of my "stock holders". They come each year and really take an interest in my home. This year (2018) They assisted in my replacing the sofa . Kathy even picked out new throw pillows for the sofa and cushions for the side chairs. Frankly all of us at HOLIDAY HOUSE have great guests that return each year. It makes having a vacation rental worth while."
Ed and Wendy De V.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
Stayed: June 2017 Submitted: April 30, 2018
Host response
"Ed and Wendy are too "stock Holders" as they come each year it seems and enjoy the place. I am really blessed to have such folks that take such a great interest in The Osprey Nest.The other owners at Holiday House take a real interest in the property and making sure it is in perfect condition for the guests to enjoy. We work well together."
Susan W.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.
Stayed: December 2016 Submitted: April 30, 2018
Host response
"Susan was fun to book again this year. In our conversation she asked "Don, have you considered replacing the sofa" ? Heck I thought I was the only one who didn't like it....it was relatively new! Susan and I got busy on the internet looking at what might be a suitable replacement....I like lady's input. I ended up with a beautiful new leather sofa and other guests in February assisted getting it installed. It was fun working that out."
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