Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!
House in Upper Matecumbe Key, FL
10 guests · 5 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
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 & separate shower, double vanity sinks etc. Separate bedroom with two twin beds, tv, a/c, etc. adjacent to kitchen. Spacious 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
Come, Relax & Enjoy!
Keywords: House
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
TV
Garden
Map of Upper Matecumbe Key, FL
$$$$
Ratings and reviews
Summary of reviews
Outstanding waterfront property with spacious accommodations, well-equipped kitchen, stunning views, and a variety of activities including swimming, boating, fishing, and snorkeling. Excellent communication with the host and a truly memorable experience for families and friends. Highly recommended!
10.0 / 10.0
Excellent place. Would definitely return. Just was very attentive to all our needs
10.0 / 10.0
It was a wonderful week. Home was fabulous and very clean. Great area near everything! Pool and jacuzzi were on point. Judy was very helpful with my booking. Definitely recommend staying here! Worth every penny! Thank you for sharing your home!
10.0 / 10.0
We had an amazing time! The house is spacious, and perfect for a family! We had 2 toddlers and they graciously put the safety gate up around the pool! The views are unbelievable. We rented paddle boards and kayaks for the week that were delivered to the home. The beach area is a perfect spot to take off for a quick swim, snorkel, or ride. Would definitely come back.
10.0 / 10.0
Host was amazing and easy to communicate with. Very clean property. House was well stocked with everything you may need. Pool and shot tub were awesome for the kids. Dock and Bay Area were amazing. Would absolutely recommend.
10.0 / 10.0
This is a beautiful home in a perfect location. The interior is cozy, kitchen has all you need, heated pool is perfect for the cooler Keys days that we had. Judy was super responsive to all questions. We really enjoyed kayaking on the bay and cooking in so we could dine looking out over the beautiful landscape! Would love to return one day!
10.0 / 10.0
House has it all. Great location, great host, everything was wonderful.
10.0 / 10.0
We loved Osprey Villa! We were a party of 6. Parents, and 2 children/couples. (20s) Tne house was spacious! We all had our privacy and the common areas were great! The kitchen was super well stocked! Pool with floats! The dock was beautifully and protected for our 24’ CC. Judy was so easy to deal with! We will definitely be back!
10.0 / 10.0
This property was very well appointed-little things like paper products, coffee, spices that make a stay easier. Large kitchen for preparing meals,spacious common areas. Grounds were neat and tidy. Landlord was accommodating and available. Already booked for next year.
10.0 / 10.0
Clean quiet and tranquil.
10.0 / 10.0
This was our first family vacation since covid changed everything and we had an outstanding experience. The pool was really big and warm, the hot tub was a great option, and the place was equipped better than anywhere we have stayed. We rented a boat from A1A and used the dock at the house. We went out to the sandbar in front of the Post Card Inn and had a blast. We had nine people in the unit and we NEVER felt crowded or cramped. The kitchen was so well equipped with everything we could have asked for.
The furniture could use some updating but I wouldn't let that sway you away from this place. Overall, 5 stars and an outstanding experience.
10.0 / 10.0
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!
10.0 / 10.0
Wonderful!!
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!!
10.0 / 10.0
Family Vacation
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.
10.0 / 10.0
Excellent getaway for the whole family
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.
10.0 / 10.0
April 2022
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!!!
10.0 / 10.0
Hopefully stay here again
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.
10.0 / 10.0
Family vacation
Great time children and grandchildren
10.0 / 10.0
Private oasis
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! :)
10.0 / 10.0
Excellent accommodations and location, host went above and beyond to make a great experience.
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
10.0 / 10.0
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!
10.0 / 10.0
OUR OWN PRIVATE RESORT!
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!
10.0 / 10.0
love
The ocean is awesome!!!
10.0 / 10.0
Awesome Vacation House
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.
10.0 / 10.0
Wonderful return visit
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!
10.0 / 10.0
birthday bash
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
10.0 / 10.0
Outstanding pool and dock areas.
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.
10.0 / 10.0
Five Star + Rating
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!
10.0 / 10.0
Beautiful Home and Property
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.
10.0 / 10.0
Great place
Perfect family vacation home
10.0 / 10.0
Great time for all
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.
10.0 / 10.0
Setene
Petfect
10.0 / 10.0
Excellent
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!
10.0 / 10.0
Amazing house and stay in Islamorada!
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!
10.0 / 10.0
Lovely house close to it all but quietly tucked away
Amazing house with views for days! Very clean and the owner was always quick to respond. Will definitely stay here again next time we are in the keys.
10.0 / 10.0
OUTSTANDING
This property was nothing but amazing. We loved everything about it and especially enjoyed our friendly visitors at the docks. We named a cute manatee Osprey.
10.0 / 10.0
Great Vacation Holiday w our 4 Grandchildren (Ages 3 - #9 & 1 #11)
Perfect House for a Family Holiday! Swimming from Kids Kids loved Swimming in beautiful Pool from Dock in Bay. Fishing from Dock . We all really enjoyed each nights Family Dinner w lots of conversation. Beautiful Sunsets from House over Bay each night. Lots of space in House and surrounding grounds perfect
10.0 / 10.0
The Mississippi River Rats from Wisconsin!
We had a great week! Time goes by way too fast ! House was well equipped with everything you need! We used the pool every day , it worked well for 3 kids under 4! Thank you so much for sharing your home !
10.0 / 10.0
Perfection
We had a wonderful time at this property in Islamorada! We kept our boat at the dock, fished every day, and ate our catch each night. Thanks!
10.0 / 10.0
Phenomenal stay in the keys
Osprey bay villa is a great property in a great location. We loved the pool, hot tub, and dock. Judy was attentive without being overbearing. Lots of things to do in the area. The house was comfortable. The master bedroom and suite was massive. Everything was well maintained.
We caught lots of fish off the dock- live shrimp after sunset were the trick. The kids loved it!
10.0 / 10.0
Warmest pool ever!!! Great Seafood Nearby
We loved everything about this property. The views of the Gulf were amazing. Absolutely loved the views from level 2. The pier was great to watch sunsets from and watching fish (blue parrotfish were abundant), iguanas and pelicans. We spent many hours relaxing by the Gulf and the pool. All of us really enjoyed the pool and hot tub. The kitchen was amazing with two sinks, two microwaves and two ovens, not to mention the plethora of spices. Having a frig for food and one for bait was great. We caught 14 yellowtail snapper off of the Miss Islamorada and grilled/fried them for dinner -- delicious. We got our first ever stone crabs from Cae Sa Mer in Tavernier. All in all an extremely satisfying visit for 6 adults and 4 children celebrating two birthdays!!
FAQs
How much does this house cost compared to others in Upper Matecumbe Key?
The average price for a rental in Upper Matecumbe Key is $519 per night. This rental is $928 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!. Enjoy the water!
Is Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!! pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!?
We found 12 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and fireplace.
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