Our family had a wonderful stay at this property. Everything was well maintained, and we enjoyed using all the amenities offered. We are looking forward to another stay in the future.

Beautiful and spacious home on the beach with all the amenities needed for multigenerational family vacation fun.

This was an incredible property with many amenities! Beautiful ocean front. We loved the pool, pickleball court, and available kayaks. Lots of dining opportunities but just as fun to cook at the house and enjoy the view. Our host was very responsive and communicated easily. A wonderful few weeks!

House is amazing! Views are gorgeous! So much to do to keep everyone entertained. Property manager and owner were very responsive and handled any minor issue that came up immediately. Will be back!!

Overall, it was a tremendous week! The property has a gorgeous setting and tremendous amenities. We greatly enjoyed the pickleball court and the putting/chipping green in the front of the property. In addition; all of the kayaks and paddle boards were tons of fun! The kids really enjoyed snorkeling and fishing off the dock. The property manager was easily accessible and answered all of our questions, which was tremendously helpful during our stay. The pool and hot tub could use a little work, but we’re very enjoyable throughout the week! Huge thank you to the “pool guy” who came and cleaned on Friday morning. The primary negatives would be on the inside of the house. There are a few items that are beginning to be worn out and in need of some maintenance or replacement. Beds, pillows and linens could use “freshening up” and a little more attention may need to be placed on some area with some potential mold growth. The kitchen was well stocked and had lots to offer. Overall, another tremendous week and was greatly enjoyed by all! Thank you again for allowing us to stay!

The house is full of recreational activities. Our family enjoyed all of them. The pickleball court was a huge gathering place as well as the pool. The house is an awesome place for family to gather. The dock is wonderful to enjoy all the sea life that goes by. The owner did a terrific job of supplying restaurants and activities in the area. We loved our stay and would definitely stay there again if we have the opportunity to do so.

Great property with no issues. Everything was as advertised and went smoothly. We will come back and rent this property in the future.

Owner is always available and responds quickly House is big with a beautiful layout and plenty of windows! So many places to hang out both inside and out. Awesome pool, pickle ball court (great idea!), putting green, ocean toys. House and all details are well thought out. A really comfortable spot to spend a vacation in. There is an event type house next store that can be very loud at night on weekends. That is the only downside. Very grateful to the Owner for answering all questions!

Beautiful Property with stunning views from backyard and pool. So much to do you really don’t need to leave. leave….just about every activity you can imagine! While close to the road, really not an issue. Highly recommend!

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.