Private Beachfront Estate with Resort-Style Pool & Pier

We love the property. The weather didn’t comply with our wishes, but the pool and hot tub, games etc more than made up for chilly temps. It’s a beautiful place, awesome location, and the six of us who stayed there highly recommend it. The only caveat is for those intent on fishing off the dock, as some of our crew were. It’s too shallow, at least when we were there. We did see some very cool sea creatures, and it’s beyond beautiful.

Michael was very friendly and helpful. Well maintained home with a beautiful view

Beautiful property equipped with everything we needed. A nice, peaceful week enjoyed by all!

The house is great especially with a large group like we had - lots of activities, great beach and pet friendly. Michael was responsive and easy to work with if we had questions.

Great property and property management.

What a beautiful home! The property had everything we needed to buy some groceries and stay on-site (although we did some exploring and a boat cruise). The pool and hot-tub were the center of our evenings. Would highly recommend to anyone staying in the Keys.

House is perfect for a family vacation. Amenities are fantastic.

This is the second time staying at this location. Everything was excellent. The sea grass on the beach was horrible. This is the only complaint out of 2 stays. But it met our needs and grandkids loved it.

There were 10 of us, 5 adults and 5 kids ranging from 10 to 14 and couldn't have asked for anything better. While there are various things you can do while in the Keys the property itself had PLENTY to do and really no reason to leave. On top of the pool and hot tub we totally took advantage of the pickleball court, the putting area, ping pong table, pop-a-shot basketball, the 2 bikes to just ride around the property, the bar/tv area next to the pool, playing cornhole, kayaks, paddleboards and then the dock for views/fishing. The way the palm trees are set on each side of the back of the property create an absolute amazing visual from the back of the house and looking out at the ocean and dock during sunrise, sunset and when the moon is out. Truly amazing.Within a 10 minute drive you'll come across a grocery store, CVS and lots of restaurant options and while there's only 1 road through the Keys the flow of traffic was a non-issue from the property to wherever we needed to go.Highly recommend this property for a large group especially if you have kids with all of the activities that is offered which allows you to truly to not have to leave. Cheers!

This was our 2nd time at Southwinds.The 1st time when we arrived, the cleaning people were still at the villa cleaning. They did an excellent job. On our 2nd visit when we arrived no cleaning people were there. When we walked in, [it did not smell like it had been cleaned for a while. Things were dusty, the floor did not seem clean. The bedding and towels were all washed and the beds made. It seems like Southwinds needs some tender loving care. We had a wonderful time, it just could have been a little

The view is amazing!

Truly enjoyed another stay at this property. Very private , spacious and clean. It’s truly the best property in Islamorada for an authentic Florida Keys getaway.

Excellent home. View is fabulous. Extremely nice home. My two sons, daughters in law and four great children and my wife, 10 in all had plenty of room and ver comfortable. Highly recommend this home fora family vacation.

We are a family of 10 - 8 adults, 2 children under the age of 5. This property was perfect for our family. The family room and Kitchen is a perfect size for a large group. There is plenty to do onsite. I would highly recommend this property to anyone that has a large group. You will have time together and still have plenty of space if you like to spread out.

Beautiful home -hard to leave-didn’t really need to leave. You thought of everything, and we loved it!

Well stocked home with plenty to do in and around the house. Amazing views with water sport equipment and a long dock with good fishing.

Very well appointed vacation home. Stuff for all ages to do on the property and the laid back location was excellent just for relaxing at its best. Grandkids really enjoyed activities on the property. This place is a must for a relaxing vacation.

We travelled from Richmond, Virginia to have a family vacation in this home and it was absolutely amazing. It could not have been better - the communication with the owner and the property manager was incredible and the home and views were perfection. It’s never fun when vacation ends but we had such a wonderful time on this trip, it was so sad to leave! Thank you for everything, we hope to be back!