We had a great time at this property, highly recommend! Views we’re amazing from all balconies/decks and the location was perfect for restaurants, shopping, etc. Mike the host was very helpful and we hope to stay here in the future!

We have been coming to Islamorada for 25+ years. This was our first time staying farther outside of the town, but the house had everything we ever needed, so we didn't feel like we needed to leave. We had cooler than expected temps, but the Pickleball Court was a huge hit with the whole family. The outdoor Fire Pit did not work the week we were there. Some of the bath towels could use a freshening up, but overall couldn't ask for a better place to gather with a group of 12 to celebrate Christmas. Islamorada will always have our heart!! Owner Mike and Property Manager Mike were very easy to communicate with during the book process and during our stay. Thank you so much! We hope to come back soon!!

Southwind never disappoints. Wonderful place to spend time with family. We love all of the activities there are to do on the property. The ocean is filled with so much wildlife to see everyday off of the dock. There is always something to do. We will be returning.

This was our first visit to the Florida Keys and it did not disappoint. Property was perfect for our extended family (kids: 3-12, 6 adults) and as expected. Pictures and description are accurate. Pool/Hot Tub/Beach Bar was our favorite location, and we took full advantage. Kids enjoyed fishing off the dock nearly every day and could easily catch a variety of fish. We didn't swim in the ocean due to the high winds from Hurricane Nicole but enjoyed the beach setting especially the hammocks. All entertainment amenities (i.e. kayaks, canoes, snorkling, pickle-ball, golf, etc.) were as described. Mike (owner) was very easy to communicate with and extremely responsive. Overall a fantastic vacation and great property. Highly recommend.

The property was beautiful, the gate to the property failed, I messaged Mike and he fixed it right away! Will come back

Incredible property and home! Beautiful!

Our family had the best time at this property. The home was spectacular, pool and hot tub were very nice, and there were so many extras. Everyone had a great time on the paddle boards, kayaks, canoes, golfing on the putting green, and playing pickle ball. The kids loved seeing the sharks when snorkeling and just standing on the dock. The property was beyond what we expected. We will be back!!

Our family had the best time at this property. The home was spectacular, pool and hot tub were very nice, and there were so many extras. Everyone had a great time on the paddle boards, kayaks, canoes, golfing on the putting green, and playing pickle ball. The kids loved seeing the sharks when snorkeling and just standing on the dock. The property was beyond what we expected. We will be back!!

We gathered as friends to enjoy some days in the sun! South wind Estate was lovely for this. This would be a fabulous rental for multiple families. So much on the property to do!

Everything was great with the exception of the doc which is not suitable for boats

We love the property the view was amazing and the house was amazing. Looking ditto another vacation in this beautiful beach home again in the future.

We love the property the view was amazing and the house was amazing. Looking ditto another vacation in this beautiful beach home again in the future.

Everything was great with the exception of the doc which is not suitable for boats

Spoke with Mike couple times prior to our week found him to be cordial, honest and a true professional in all aspects of the word ! His property was as described and over the top ! As nice as I’ve experienced in 40 years of travel both stateside and abroad😎I will be BACK

The property was an absolute dream. Our family of 7 enjoyed everything from the pool, to the beach, to fishing off the dock. We greeted the property manager Mike upon our arrival and he was quick to respond when we had questions. It was an unbelievable home and we will be back again!

Southwind is absolutely amazing, there is something to do for any age, our group was 3 families age ranging from 10 - 65. There is plenty of space for everyone to spread out and do their own thing if they want. The pickel ball court and putting course were an added bonus as they were just completed before our stay. If your looking for a high end rental with all the amenities this is the place!

This vacation home is fantastic! First the property manager, Mike Klimpl greets you shortly after you check in to ensure that everything is ok and you are happy. Later in the week we had an issue with one of the dryers, we called Mike and it was fixed in less than 2 hours. great communication and service. The house was spotless, laid out perfectly for great views and plenty of space for 5 couples. The private beach is soft white sand with beautiful lighting at night. There are plenty of seating spots for people to enjoy different views in the Sun or shade. The amenenities are like your are at a private resort. Paddle boards, kayaks, fishing rods, pickle ball court, putting greens, basketball game, corn hole, and bikes all there for your enjoyment. The pictures can’t do this place justice, it’s more magnificent than we imagined. Private, quiet, and everything you need for your own Private resort. We have stayed in the Keys 5 times now and this vacation home is simply the best by far.

The place was clean with great views and lots of stuff to do on the property. You won't be disappointed staying here. We will definitely be back!

Easy if available.

This home was perfect for our fun family vacation!

This home was perfect for our fun family vacation!

This is a beautiful, spacious, beachfront home with all the amenities you could need. It is as pictured but actually the pictures don’t do it justice. The property is immaculate, the home was spotless and decorated with modern decor throughout. Floor to ceiling windows across the back of the home allow perfect views of the water. Our group consisted of two families with teenage and small children and there were clear-bottom kayaks and paddle boards for all of us to use. We spent most days taking advantage of the private beach area and easy entrance to the ocean. Very little waves and crystal clear water allowed us to see all kinds of marine life and the kids loved fishing from the private pier. The kitchen was fully equipped with everything we needed to cook meals if we chose to stay in but this house is perfectly located to some great restaurants and popular local attractions as well. We had outstanding customer service from Mike, the property manager as well as Michael the owner. Mike took care of making sure the bikes had new tires so we were able to take bike rides and enjoy the bike path along the island. Michael was immediately available and responsive to answer any questions we had about the property. We have rented other beach homes in various areas and overall this house is a top rate, high end rental I would certainly recommend and return to.

This is a beautiful, spacious, beachfront home with all the amenities you could need. It is as pictured but actually the pictures don’t do it justice. The property is immaculate, the home was spotless and decorated with modern decor throughout. Floor to ceiling windows across the back of the home allow perfect views of the water. Our group consisted of two families with teenage and small children and there were clear-bottom kayaks and paddle boards for all of us to use. We spent most days taking advantage of the private beach area and easy entrance to the ocean. Very little waves and crystal clear water allowed us to see all kinds of marine life and the kids loved fishing from the private pier. The kitchen was fully equipped with everything we needed to cook meals if we chose to stay in but this house is perfectly located to some great restaurants and popular local attractions as well. We had outstanding customer service from Mike, the property manager as well as Michael the owner. Mike took care of making sure the bikes had new tires so we were able to take bike rides and enjoy the bike path along the island. Michael was immediately available and responsive to answer any questions we had about the property. We have rented other beach homes in various areas and overall this house is a top rate, high end rental I would certainly recommend and return to.

This property is beautiful and very spacious. It was excellent for a multi generational family holiday reunion.

We felt we were on our own private island! If I were to own a Beach front home this would be the one. The house was perfectly set up for the ocean views and all the amenities and toys available for the beach and Poolside with bar side bar & our door TV

We felt we were on our own private island! If I were to own a Beach front home this would be the one. The house was perfectly set up for the ocean views and all the amenities and toys available for the beach and Poolside with bar side bar & our door TV

We absolutely loved staying in this home. It was perfect for two families of 5. The pool is fantastic and we made ample use of the kayaks and paddle boards. The owner is very responsive. We couldn't find children's life jackets so they ordered more from Amazon right away. Looking forward to staying in this home again in the future!

This property is beautiful and very spacious. It was excellent for a multi generational family holiday reunion.

This was our second time coming to Southwind. There is a lot to do without leaving the house. The house provides unlimited views of the ocean which is fantastic. Good home for all ages. We will be returning.

This property was everything it said it was and more. What a wonderful place with a fantastic view. Thank you

This property was everything it said it was and more. What a wonderful place with a fantastic view. Thank you

Some small details but overall a very enjoyable stay. I would return.