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Bayfront 2/2 Villa , Boat ramp, Marina & trailer storage. Great central location

Safe and well lit boat dockage in our sheltered harbor
Safe and well lit boat dockage in our sheltered harbor
1/57
1/57

About this property


Islamorada Villa

  • Sleeps 4

  • 2 bedrooms

  • 2 bathrooms

  • 671 sq. ft.
14 reviews


Amenities


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Rates

Rental basis: Per property
Rental rates quoted in 
Rate PeriodNightlyWeekend NightWeeklyMonthlyMin 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

View all periods


Fees:

  • Pet fee (non refundable): $150
  • Cleaning Fee: $150
  • Guest fee per night: $100
  • Tax Rate: 12.5%


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.


Availability

Last updated on May 03, 2025

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20Available     20Unavailable    

Location

Nearest Airport

: Miami International Airport - 80 miles

Nearest Bar

: Islamorada Brewery & Distillery - 100 yards

Nearest Beach

: Anne's Beach - 5 miles

Nearest Golf

: Cheeca Lodge - 0.5 miles

Nearest Theme Park

: Theater of the Sea - Dolphin Encouter - 1 mile

Nearest Restaurant

: Bayside Gourmet - 500 yards

Frequently Asked Questions

Reviews

from 14 reviews
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review

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: Submitted: October 07, 2024

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review

Beautiful place!!

Couldn't have been any better. Perfect location, comfortable beds, great views! The deck right out the door was our favorite place to be. Highly recommend the Nest

Stayed: Submitted: January 01, 2024

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review

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: Submitted: October 08, 2023

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review

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: 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"

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review

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: 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!"

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review

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: 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"

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review

Mark and Dolly

Absolutely fantastic place to stay, we will definitely be back

Stayed: Submitted: July 15, 2018

Host response

"New guest with great feed back. Don"

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review

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: 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."

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review

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: 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!"

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review

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: 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."

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review

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: Submitted: May 13, 2018

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review

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: 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."

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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: 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."

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review

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: 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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