There were 10 of us (8 adults & 2 children) who stayed at Osprey Bay during the week of Thanksgiving. The house was better than in the pictures. Before we arrived I was worried about having having 5 bedrooms and 3 baths. But it wasn’t an issue at all. We were rarely inside. We were in the heated pool, hot tub or snorkeling off the dock most of the time. We saw so many varieties of colorful fish, octopus , sharks, and a huge hermit crab right off the dock! We rented a hurricane boat through A1A water sports . We planned to use it every day to go to the reef and snorkel. We actually went 2 times but we saw more fish by the dock at the house. So we used the boat to explore the area, the islands and look at the huge houses nearby. We all like to cook so we made a lot of meals. The kitchen looked newly remodeled. It had everything we needed and more! Everyone wanted fresh seafood with every dinner we ate at the house so we went to Lobster Walk to buy fresh seafood several times. We ate at Robbie’s, Lazy Days, Lor-e-Lei, and Islamorada Brewery. We liked them all. We went to Theater of the Seas. If you go make sure you do “meet the sea lion” program. It was our favorite. We do a family vacation every 2 years. We’ve gone to outer banks, Mexico, Honduras, and Belize. Everyone said this was our best trip. It was because of the house, grounds, location, and amenities. We loved the beachy vibe of the house and loved how comfortable it was. There was plenty of room for all 10 of us. The Florida Keyes are beautiful and there so much to do and see. We hope to be back in 2024!

This was a fantastic place! It had everything we needed inside and out. We spent most of our time on the dock fishing and enjoying the water. Besides the amazing fish, including nurse sharks and lemon sharks, we saw manatees almost everyday. The pool and eco area were great and had tons of pool rafts/toys. The house was one of the most fully equipped houses we’ve stayed in. Everything was labeled and easy to find and in great condition. Would love to stay here again!!

This property is exceptional and exceeded all of our expectations! The entire week was filled with memorable experiences that we enjoy as a family: boating, kayaking, fishing, snorkeling, wildlife and overall experiences the outdoors offers. Also there are great restaurants and bars in close proximity by boat and car.

Does what it says on the tin. Great location and Judy and Ken made us all feel very welcome. Hopefully we will all return in the near future.

The BEST we have stayed in in the keys. We have been going to the Keys for 30 years. This was the best experience from booking to the end. Judy was very accommodating and thoughtful!!! We are hoping to make this an annual trip to this property!!!

The BEST we have stayed in in the keys. We have been going to the Keys for 30 years. This was the best experience from booking to the end. Judy was very accommodating and thoughtful!!! We are hoping to make this an annual trip to this property!!!

Loved the location. The back yard is like an oasis with the privacy, the pool, hot tub and the dock. Saw lots of fish, dolphins and even a shark one evening. House has plenty of space for a group, so you don't feel like you're on top of each other. We all spent most of the time outside and the spacious dock, deck and pool areas. House is dated, but very well maintained and cleaned.

Loved the location. The back yard is like an oasis with the privacy, the pool, hot tub and the dock. Saw lots of fish, dolphins and even a shark one evening. House has plenty of space for a group, so you don't feel like you're on top of each other. We all spent most of the time outside and the spacious dock, deck and pool areas. House is dated, but very well maintained and cleaned.

Great time children and grandchildren

Great time children and grandchildren

What an amazing way to ring in 2022 and spend my 50th birthday with friends and family. The house is spacious and well-equipped, but the pictures don't do justice to the outside space. The weather wasn't fabulous, but that's ok when you have a heated pool and hot tub overlooking the water and snorkeling off your own dock! We ranged from age 10 to age 80, and every single person enjoyed the relaxed environment created by Osprey Bay Villa. Thank you, Judy, for sharing your home with us! We are already looking to come back next year! :)

Very satisfied with the property and access to all Islamorada has to offer. Property is exactly as pictured and described on the vrbo site. Host was great with communication and hospitality. Would book again

I was told, within minutes of check-in, by my family, ‘Mom, you knocked this one outta the park!’. Judy was immediate in her replies to my inquiries, the home was spacious, clean, well-stocked, and lovely. The grounds were manicured and tended to, the pool & hot tub were spotless, and our time at Osprey Landing couldn’t have been more enjoyable. One really does not need to leave the home but, CVS is a block away & Publix is .5mi. We rented a kayak & paddleboard which were delivered right to the water for us by a local company Judy recommended. The snorkeling right off the dock was unbeatable, too!! Can’t say enough about our week at Osprey Landing. The home is “old Florida” and we loved every second. Thanks again, Judy!

Beautiful property! Amazing view. Very nice dock and pool. Centrally located to everything in Islamorada. Judy was very helpful with check-in and couldn’t have been more accommodating. Highly recommend Osprey Bay Villa!

Beautiful property! Amazing view. Very nice dock and pool. Centrally located to everything in Islamorada. Judy was very helpful with check-in and couldn’t have been more accommodating. Highly recommend Osprey Bay Villa!

I was told, within minutes of check-in, by my family, ‘Mom, you knocked this one outta the park!’. Judy was immediate in her replies to my inquiries, the home was spacious, clean, well-stocked, and lovely. The grounds were manicured and tended to, the pool & hot tub were spotless, and our time at Osprey Landing couldn’t have been more enjoyable. One really does not need to leave the home but, CVS is a block away & Publix is .5mi. We rented a kayak & paddleboard which were delivered right to the water for us by a local company Judy recommended. The snorkeling right off the dock was unbeatable, too!! Can’t say enough about our week at Osprey Landing. The home is “old Florida” and we loved every second. Thanks again, Judy!

The ocean is awesome!!!

The entire process was very smooth....from booking all the way to check in. The property is beautiful and perfect for a getaway. So many things to do around the house including swimming, shopping, restaurants, snorkeling and fishing. I would highly recommend.

We love Osprey Bay Villa! Our group of friends and family enjoyed another fantastic week here. It is a beautiful property and the house is always spotless and has everything you need. There was plenty of room for our group of 11 and we spent the week lounging around the pool and getting plenty of use from the hot tub too. The house is located right in the heart of Islamorada near all the great shops and restaurants. And Judy is a pleasure to deal with. We left an item there by accident and she had it quickly located and on the way back to us. We can't wait to come back again soon!

The house was everything shown in pictures. We had a wonderful time. Only complaint was none of the tvs worked. Location was good in between Key West and the Everglades. However being the week after Labor day some restaurants were not open

The house was everything shown in pictures. We had a wonderful time. Only complaint was none of the tvs worked. Location was good in between Key West and the Everglades. However being the week after Labor day some restaurants were not open

We all felt privileged to stay at such an incredible property. Ten people total and we all were very comfortable. The property is very well maintained, but by chance the washing machine and one of the garbage disposals went down while we were there and the owner had them both fixed within a day. We could not ask for more. Also felt blessed to see a manatee on multiple occasions, usually about 8 am - just be patient.

Loved this place and area! Everything exceeded our expectations! The home has it all & more. The marine life at the dock was like having a reef at the back door. Wow! We could( and did) just sit there watching for hours. Judy went above and beyond with customer service. Thank you for such memorable trip for my daughter's graduation. We will be back!

Loved this place and area! Everything exceeded our expectations! The home has it all & more. The marine life at the dock was like having a reef at the back door. Wow! We could( and did) just sit there watching for hours. Judy went above and beyond with customer service. Thank you for such memorable trip for my daughter's graduation. We will be back!

We had a fabulous time spending a week at this property. The beautiful pool and dock gave us the opportunity to relax and not feel like we had to always be on the go. Great hosts. This is our 5 year renting a home in Islamorada and by far the best property we have been to.

We had a fabulous time spending a week at this property. The beautiful pool and dock gave us the opportunity to relax and not feel like we had to always be on the go. Great hosts. This is our 5 year renting a home in Islamorada and by far the best property we have been to.

Perfect family vacation home

Judy was wonderful to work with and was extremely responsive. The house was perfect and the aquatic life and sunsets made the trip extra special. Everyone had a wonderful time and want to return.

Petfect

Petfect

This is our second time staying at this property and we love it. The listing is accurate and the owner is very helpful. Thank You!

We had a fantastic week at Osprey Bay. The house and grounds are just perfect for a relaxing but active getaway. There was plenty of room for our group of 9 and the house was well appointed with everything we needed. We also appreciated Judy's great communication. We are looking for another date to come back and stay!