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Spectacular Panoramic Sunsets in Islamorada Bayfront Villa!!! Licensed-#VR-171

Bedrooms 5
Property type house
Minimum Stay 7 nights


About the property

House, 5 Bedrooms, 3 Baths, (Sleeps 10-12)

OSPREY BAY VILLA! Wonderful Bay front Home in the heart of Islamorada in the fabulous Florida Keys for rent by the week, or month; offering incredible panoramic bay and sunset views. Heated pool & hot tub, sunning decks galore. Deep water dock & boat basin. Elegant, yet casual, spacious living room with coral rock fireplace, wet bar, open dining room, atrium garden,& gourmet kitchen. Sleeps 10-12 people comfortably. Private south wing offers 3 bedrooms; 1 with1 king bed, 1 with 1 queen bed, another 1 with 2 queen beds, and 1 full bathroom with bathtub & shower, double vanity sinks etc. Separate bedroom with two twin beds, tv, a/c, etc. adjacent to kitchen. Huge second level master bedroom suite with king bed & it's own master bath & vanity room, fireplace & bay side veranda. Third full bathroom with vanity and shower downstairs has an entrance from the wet bar/living room area & also exits to and from the heated pool. Lush tropical landscape & expansive waterfront lawn & dock area with its own small beach for wading into bay, for snorkeling or for an easy launch for kayaks and paddleboards. This vacation home is secluded, yet situated in a perfect location for walking to classic restaurants & local shops.

Come, Relax & Enjoy!

Keywords: House

More Details


Islamorada House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 12
  • Max. adults: 10
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • No Jet Skis, Wave Runners, or Ultra Light Gliders are Allowed. No RV's and/or Motor Homes are Allowed.
Location Type:
  • Waterfront ...
  • Air Conditioning
  • Clothes Dryer ...
  • Hair Dryer
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Parking Off Street
  • Parking for RV/Boat/Trailer
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Wood Fireplace ...
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Pantry Items
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 3 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
  • 5 Bedrooms, Sleeps 12
  • Bedroom 5 - 2 twin/ single
    Bedroom 4 - 1 queen
    Bedroom 2 - 1 king
    Bedroom 1 - 1 king
    Bedroom 3 - 2 queen
  • King size beds (2), Queen size Beds (3), Twin or Single Beds (2)
  • CD Player
  • DVD Player
  • Music Library ...
  • Satellite / Cable
  • Stereo
  • Television ...
  • VCR
  • Video Library
  • Balcony
  • Deck / Patio
  • Lanai / Gazebo
  • Lawn / Garden
  • Outdoor Grill
  • wheelchair accessible
Pool / Spa:
  • Heated Pool
  • Hot Tub
  • Private Pool ...
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • ruins
  • synagogues
  • water parks
  • zoo
Leisure Activities:
  • bird watching
  • boating
  • eco tourism
  • paddle boating
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • jet skiing
  • kayaking
  • paragliding
  • parasailing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Bay front, Boat Basin & Deep Water Dockage, Heated Pool,& Spa, Lush, Tropical, Landscape Abundant Sun Decks.


Wonderful! 4.9/5 -
(12 traveler reviews)

91% Complete
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Spectacular Panoramic Sunsets in Islamorada Bayfront Villa!!! Licensed-#VR-171
average rating of 4.9166665 based on 12 reviews

Absolute perfection for 3 generations of our family

  • 5 of 5

We have taken house rentals in Islamorada since our own children were high school age. In those years, it was about having enough room for our daughters and any friends that came along. The very nature of the island provides everything any age could possibly want in a very close radius. Now, we come in a group of husband, myself, two daughters, their husbands and four grandchildren, ages 5 and 2. Now our rentals have to have something for everyone. Osprey Bay WAS the perfect match, in every way. First, and foremost, the owner is exceptional to work with, no matter what the request. The house, pool, beach area, spa, dock, grounds...entire property is extremely well maintained, immaculate, and they desire to keep it this way. Very important on a rental. They leave pool toys, fishing gear, plenty of towels, extra toilet paper in every bathroom and kitchen supplies. It is as if you were taking a friend's house for a week. None of which is typical in vacation rentals. The kitchen is stocked beyond the basics and everything worked as you would hope they would, including a wonderful ice maker in the indoor bar. All linens were top quality, so much so that one daughter checked to see what kind of sheets they were, because she wanted to get some. And the SUNSETS!!!! Spectacular, and you don't have to leave the property. Thank you for allowing strangers to rental your wonderful property. As a special note, the bedroom upstairs is a suite, and offers total privacy AND views. We stayed up there, while all the kids and grandchildren slept on the first floor. To anyone traveling with a large family, THIS is the best. We got to sleep in, shower, dress in complete privacy.

  • Submitted: Apr 2, 2017
  • Stayed: February 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Kathleen for the stellar review! We, at Osprey Bay Villa, do try to provide a comfortable, welcoming home to all of our "Families". Over the years, many of these families have become close friends of ours. Of course, the very fact that Osprey Bay Villa is located in the heart of Islamorada, my "Island in the Sun", lends graciously to the ambiance of the property. With the Florida Bay right at your footsteps and the truly spectacular sunsets, it's a very desirable home in which to vacation. Thank you again Kathleen and family for your vacation visit. We hope to see you again in the future. Judy & Ken & crew
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The best place to stay in Islamorada!

  • 5 of 5

Six of us recently stayed at Osprey Bay - myself and my husband, our two children (ages 7 and 10), and my parents. This home was perfect for us! We had more space than we needed (could have easily added another 4-6 people) but we loved not being on top of each other and having the space to relax and spread out. The house is immaculately clean and has everything you could possibly need. We have been renting in Islamorada for ten years, and we have never had a house that had all possible kitchen needs until this one. We were able to cook just like at home. The pool and hot tub are great, and we used them for hours every day. The views are spectacular, and we loved hanging out on the dock. We saw a manatee and an octopus, and tons of fish. The homeowner was so easy to work with before and during the rental, and we accidently left a few things at the house which she mailed to us without any problem - what a joy to work with her! The location is the best - so close to so many good restaurants. I cannot say enough good things about Osprey Bay - and we will definitely be back!

  • Submitted: Jan 8, 2017
  • Stayed: December 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Jennifer for choosing Osprey Bay Villa for your Christmas holiday vacation for you and your fun family. My crew and I always strive to accommodate the guests to our utmost ability. Also, it always helps when the local abundant wildlife cooperate so well and make their friendly appearances:-) Ken and I are so happy to hear the octopus crept out for you. That is always a special delight along with the manatees too. Often times the guests also get to have the dolphins -"Flipper" types - surprise them with a splashy display in the bay. Maybe next time you and your family or friends come to Osprey Bay, the dolphin will play for you. Thank you again for your visit. Osprey Bay Villa and crew would love to welcome you back again! Have a wonderful and Happy New Year! Judy and Ken and Crew
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0 0

Magical week

  • 5 of 5

Osprey Bay--the house, the pool area, the dock, and the property overall-- are so thoughtfully designed and so beautifully, completely furnished. Truly a special, very comfortable place to spend a week. An extra bonus is the wildlife—the abundant and varied fish, the manatees, the dolphins we encountered while kayaking and paddle boarding, and of course the ospreys.

  • Submitted: Jun 2, 2016
  • Stayed: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much Karl and Elizabeth! Osprey Bay Villa was thrilled to host your family gathering. We were so delighted you were rewarded with the sweet visits from our local dolphins and manatees. What a wonderful experience to transpire while exploring their tranquil estuary during your kayaking and paddle boarding ventures. The osprey family enjoyed your visit also. We do hope you can come back and visit our "Island in the Sun", Islamorada, in the future. Thank you again for your gracious review, Judy M.
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Nice Place

  • 5 of 5

First time at this rental and we were very pleased with the accomodations. Home was very clean and well organized. We will be back! Weather could have been warmer, but, the location gave us access to many things to do.

  • Submitted: Feb 22, 2016
  • Stayed: February 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Marc! It's great to hear from you again. It's always wonderful to hear from Guests as gracious as you and your group of friends. Sorry you had to experience our first and only "cold front" of the year. I think it was in the low 50's here in the Sunny Florida Keys that week. We just wanted to make you feel at home- so we brought in some chilly Northern weather-LOL:-) Osprey Bay Villa was happy to keep you warm and toasty in our heated pool and hot tub. No "Polar Bear Club" down here:-) It will be fantastic for you to come back next year or even before. We are having 78 degree weather this week. Lots of Fun in the Sun for you and your friends now. Thank you again for writing- hope to hear from you soon. Warmest Regards, Judy M.
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Best in Islamorada

  • 5 of 5

I've been a frequent renter of multiple homes as well as temporary resident in Islamorada for over 20 years. My family just finished a great stay at Osprey Villa. Best location, best equipped vacation rental on the island. House is super functional, very cozy, great for our four couples with another bedroom to spare. Outside pool and dock area are awesome. New large deck, floating umbrella bars, rafts, snorkel gear (off the dock). Great dockage but you don't have to leave to catch eating size snapper and grouper from the dock. Osprey nest overhead, manatee at the dock, crystal clear water for viewing lots of sea creatures. The location is in the middle of the best restaurants and waterfront entertainment spots yet is very private. Highly recommend.

  • Submitted: Nov 2, 2015
  • Stayed: October 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thanks Jim! It was great to have you and your fun family visit our Beautiful Islamorada again. I'm so thrilled you came to visit Osprey Bay Villa and you were reminded of the beauty that surrounds us. I, myself, never tire of the tranquility of the flora and fauna that the Florida Bay and our "Island in the Sun" has to offer. The fact that the pair of Ospreys made it back here just in time for your visit is awesome. They will be having their chicks in a few months. It's always fun to watch them grow. Your many adventures on your "paddle board boat" on the Bay while you were visiting here was such a great pleasure. Also, so glad you caught your own dinner -fresh- right off of the dock. Those mangrove snappers are my favorite:-) Thanks for sharing your stories. Please come back again very soon & Keep having FUN!! Thanks, Judy M.
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Everything a family could want for a great vacation

  • 5 of 5

My family of 6 and my sister-in-laws of 4 spent August 15-23 at Osprey. It was by far one of the most relaxing vacation we have ever had. We have traveled all over the world and I must say I have never been to such a well equipped house. Judy has thought of everything you could possibly need from cooking, entertaining, pool play, comfort, and fish play. Judy was the most professional and caring person to deal with. She even let me ship surprise presents down for everyone. I would highly recommend YOU take your family down. The master suite upstairs was great for putting down my 6 month old grandchild for naps during the day. Everything you could possibly need is within walking distance or a short drive. We spent hours just watching the fish, manatees and other sea life from the dock. And then, there were the most incredible sunsets every night. Thanks Judy The Richardsons and Gibbons (SC,Texas,LA,Philly)

  • Submitted: Sep 10, 2015
  • Stayed: August 2015
  • Source: VRBO, from HomeAway
Owner's Response: I enjoyed your visit Marsha so very much. Meeting your family was a special pleasure . It is my joy to have my guests appreciate what the Keys have to offer and to have Osprey Bay Villa a part of the experience. My "Live-in" home is very close by, so I am very familiar with all of Islamorada, my "Island in the Sun". It is always my privilege to be able to make suggestions to my guests on shopping, sight seeing, fishing, diving, kayaking or any of the other Keys attractions. I do try and take special care to provide them with a wonderful "Home" base for their vacation visit. Osprey Bay Villa is a gracious home and loves to lend itself to Friends and Families. Providing any and all the necessities and amenities to make your stay as comfortable and relaxing as possible is my highest goal. Thank you Marsha and family for your lovely review. It is always a thrill to have Osprey Bay Villa receive these accolades. I hope to see you and your family again real soon. Thanks again for your visit, Judy
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Judy Moeller
Member since: 2008
Speaks: english
Response time:
Within 2 days
Response rate:
Calendar last updated:
February 11, 2018


Nearest Airport
80 Miles
Miami Internationl Airport
Nearest Barpub
70 Metres
The Whistle Stop
Nearest Ferry
82 Miles
Key West
Nearest Golf
1.5 Miles
Cheeca Lodge
Nearest Train
80 Miles
Nearest Motorway
25 Metres
US Highway # 1-Overseas Highway
Nearest Restaurant
0.1 Miles
Bayside Gourmet; Kaiyos, Lorelei,Chef Michaels
Nearest Ski
10 Metres
water-ski in Florida Bay- Front yard bay
Nearest Beach
7 Miles
Founder Park or Anne's Beach
Car: necessary

Osprey Bay Villa is a licensed Vacation Rental property- Vacation Rental License No. VR-171 located in downtown Islamorada, Florida Keys, just minutes away from many recreational areas such as Founders Park and

Theater of the Sea; a great marine attraction! Swim with the Dolphins, etc.

Feed the giant Tarpon at Robbie's Marina.

Snorkel or scuba dive many reefs nearby or Pennekamp Park or right here along the shoreline of the bay.

Endless fishing -Ocean or Bay or right off of Osprey Bay's dock.

There are fabulous restaurants all with in a mile of Osprey Bay.

For this & other info, you might want to contact The Islamorada Chamber of Commerce- 305-664-4503;


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee - Standard* $300 + Tax
Refundable damage deposit $1,000
Tax Rate 12.5%

Rates are subject to change until confirmation of reservation.
* Please Note: Monthly rentals are $18,500.00 and require 2 cleaning fees at $300.00 each: 2 weeks after check-in and at check-out.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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