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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

Judy Moeller
Member since: 2008
Speaks English
Response time:
Within a day
Response rate:
Calendar last updated:
20 July, 2018


Accommodation and facilities for this holiday house in Islamorada in Monroe County

Property Type:
  • house
  • Self-catering
House Rules:
  • Check-in: 16:00
  • /
  • Check-out: 10:00
  • 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 ...
  • Hob ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 3 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
  • 5 Bedrooms, Sleeps 12
  • Bedroom 5 - 2 Single Bed
    Bedroom 4 - 1 Large Double Bed
    Bedroom 2 - 1 Extra Lg. Double Bed
    Bedroom 1 - 1 Extra Lg. Double Bed
    Bedroom 3 - 2 Large Double Bed
  • King size beds (2), Queen size Beds (3), Twin or Single Beds (2)
  • CD Player
  • DVD Player
  • Music Library ...
  • Satellite / Cable
  • Stereo
  • Television ...
  • Video Player
  • Video Library
  • Balcony
  • Terrace
  • Lanai / Gazebo
  • Garden
  • Barbecue
  • wheelchair accessible
Pool / Spa:
  • Heated Pool
  • Hot Tub
  • Private Pool ...
  • churches
  • cinemas
  • festivals
  • Health/Beauty Spa
  • library
  • live theatre
  • marina
  • museums
  • playground
  • recreation centre
  • 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 centre
  • groceries
  • hospital
  • laundrette - serviced
  • 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
  • diving
  • snorkelling
  • Snorkeling/Diving
  • 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 -
(15 traveller reviews)

93% Complete
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Spectacular Panoramic Sunsets in Islamorada Bayfront Villa!!! Licensed-#VR-171
average rating of 4.9333334 based on 15 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.

  • Review Submitted: 02-Apr-2017
  • Date of Stay: 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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3 0

Great location

  • 5 of 5

Great host, house and location. Dock in backyard worked great for 27' boat. Easy access to the ocean. Great sunsets from the deck. Will be back!

  • Review Submitted: 05-Jul-2018
  • Date of Stay: June 2018
  • Source: HomeAway
Owner's Response: Thank you Matt for your review for Osprey Bay Villa. So glad you and your family had a great visit here. Yes, the sunsets are surreal at times with all those boundless viewing areas the property encompasses. The Florida Bay is your back yard and the Atlantic Ocean is right around the corner... Fun Happens Here! We certainly will welcome you back to Osprey Bay Villa anytime. Thanks so much, Judy & Ken
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Perfect For Families!

  • 5 of 5

This home is exactly like pictured!! We had 4 adults, 2 children and it was ideal with the floor plan and outdoor layout. The home is mostly single level so it was fun being on the same floor and ideal for children however the upstairs Suite was a nice retreat! We spent a substantial amount of time on the dock where at night we watched a ton of sea life. During the day, we could walk into the Ocean from the small beach or paddle board. Judy (owner) went above and beyond for our stay.......she's amazing!! We will return! (*the cleanliness of this house was better than my personal one!!!)

  • Review Submitted: 20-Jun-2018
  • Date of Stay: June 2018
  • Source: HomeAway
Owner's Response: Thank you Katie G. Osprey Bay Villa was extremely thrilled to host you and your family for your Islamorada vacation visit! Being centrally located here on Upper Matecumbe Key in Islamorada , the home lends itself well for convenient access to many fine restaurants & great shopping. Yet the property's seclusion is still well provided & has instant water entry right here on the Florida Bay. It's always so fun to see the abundant sea life in all the surrounding waters. So glad you were here to enjoy "My Island In The Sun"! Thank you again for your vacation visit and thanks a bunch for taking time to send a great review! Hope to see you for a return visit- there are still more "FABULOUS SUNSETS" to come! Warm Wishes, Judy M.
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May 2018 Family Vacation

  • 5 of 5

Our vacation was absolutely wonderful ! Life time memories were made for my husband and I, as well as our children and grandchildren. I would recommend this property over and over again. Judy and Ken were both very attentive in that we were well informed of the property.

Again, beautiful property, spacious for the family and a very important event for our family.


Nancy & Gene Powell


  • Review Submitted: 27-May-2018
  • Date of Stay: May 2018
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Nancy and Gene for your great accolades for Osprey Bay Villa! Osprey Bay Villa always strives to provide a unique and memorable experience for all of our marvelous guests. It is always pleasurable to receive these special positive remarks. Thanks for letting our future guests know that they can look forward to an exceptional home on this spacious property in our “Little Piece of Paradise” here in Islamorada- in the Fabulous Florida Keys! Ken & I and our crew thank you very much again for your visit. Warmest Regards, Judy M.
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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!

  • Review Submitted: 08-Jan-2017
  • Date of Stay: 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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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.

  • Review Submitted: 02-Jun-2016
  • Date of Stay: 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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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;


Prices & Availability

Prices for this holiday house in Islamorada, Florida Keys

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Mini Lobster Week
21 Jul 2018 - 28 Jul 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Begin Lobster Season
4 Aug 2018 - 11 Aug 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Low season weekly rate
1 Sep 2018 - 29 Sep 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Thanksgiving week
17 Nov 2018 - 24 Nov 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
22 Dec 2018 - 28 Dec 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
New Years's week
29 Dec 2018 - 5 Jan 2019
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Easter Week
20 Apr 2019 - 27 Apr 2019
7 night minimum stay
for 7 nights
My Standard Rate
7 night minimum stay
for 7 nights

Additional pricing information

Cleaning Fee - Standard* £230.49 + Tax
Refundable Damage Deposit £768.3

Rates are subject to change until confirmation of reservation.
* Please Note: Monthly rentals are $20,000.00 and require 2 cleaning fees at $300.00 each: 2 weeks after check-in and at check-out. The refundable Security Deposit for monthly rentals is $2,500. Total of Rental payments and fees including Security Deposit is due 90 days before arrival. After 90 days these fees are non-refundable unless the nights that were reserved can be re-rented.

Owner's Cancellation Policy

  • 100% refund for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Ask Owner a Question

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