Stunning Oceanfront Home located in Islamorada Florida

Combined shower/tub, hair dryer, towels, soap

5.0 / 5.0

Outstanding(57 Ratings)

House in Lower Matecumbe Key, FL

10 guests · 5 bedrooms · 7 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Great for petsBring all your friends and family, even the furry ones

Includes essentialsGarden, Pool, Pets allowed and more

About this house rental

This stunning, completely renovated 5 bedroom, 6.5 bathroom home, sleeps 14 guests. Southwind sits on 1 acre of beachfront property. Infinity edge pool overlooking the beach and ocean. 185' observation pier for fishing and relaxing. Custom chefs kitchen and large living area for everyone to enjoy. Private gated entry for the most relaxing a secluded beachfront getaway. Watch your favorite sports team at the downstairs bar or tell your favorite fishing story. We offer tons of entertainment options from ping pong table, pop-a-shot, corn hole boards, pickle ball court, putting green, and so much more.

Amenities

Pool

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Parking

Laundry

Balcony or Patio

Dishwasher

Hot tub or spa

Garden

Family friendly

Map of Lower Matecumbe Key, FL

Nearby attractions

Everglades National Park

50.5 mi

Seven Mile Bridge

48.5 mi

Florida Keys Aquarium Encounters

35.7 mi

Theater of the Sea

13.8 mi

££££

Stunning Oceanfront Home located in Islamorada Florida

££££

5.0 / 5.0

Outstanding(57 Ratings)

House in Lower Matecumbe Key, FL

10 guests · 5 bedrooms · 7 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Great for petsBring all your friends and family, even the furry ones

Includes essentialsGarden, Pool, Pets allowed and more

About this house rental

Amenities

Pool

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Parking

Laundry

Balcony or Patio

Dishwasher

Hot tub or spa

Garden

Family friendly

Map of Lower Matecumbe Key, FL

Nearby attractions

Everglades National Park

50.5 mi

Seven Mile Bridge

48.5 mi

Florida Keys Aquarium Encounters

35.7 mi

Theater of the Sea

13.8 mi

Ratings and reviews

5.0 / 5.0

Outstanding(57 Ratings)

4.0 / 5.0

Jun 2024

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.

5.0 / 5.0

Jun 2024

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!

5.0 / 5.0

Apr 2024

We loved the house and the Property. It was very clean and exactly what was described in the listing. My only criticism was that the kitchen wasn’t stocked the best considering the house can sleep up to 14 (only 9 of us). It needs more utensils, bowls etc. And there is such a beautiful porch off the kitchen, but the only place to sit was one chair or at the outdoor dining area. I would still stay here again, but just some small items that would make a difference. Thank you for letting us enjoy your home, Mike!

4.0 / 5.0

Apr 2024

Our stay was great! This beautiful house checked all the boxes for us. The location and view were wonderful. And there was plenty of things to do with the the pool, pickle ball, golf and kayaks/paddleboards. We enjoyed watching sports from the hot tub and pool! There are a few needs of maintenance, including the kayaks. We also spent a lot on the rental and thought the property could have used a couple extra touches for the price: full propane, extra garbage bags/paper towels. Overall we loved our time here and would highly recommend!

5.0 / 5.0

Apr 2024

The property is wonderful! There are so many things to do for all ages. The pool was large and clean and we all enjoyed watching sports on the outside TV while we swam. The house itself is spacious and great for families. The best part is the view. Nobody minded washing dishes with such a magnificent view from the kitchen sink! The windows on the back of the house allow you to enjoy the view all day long. It truly felt like we were on a tropical island. We also enjoyed the dock and saw several sharks, rays, barracuda and sawfish. We hope to return next year!

5.0 / 5.0

Mar 2024

Celebrated our 50th wedding anniversary with our entire family! Southwind was the perfect home to accommodate ages 1- 73. The views of the ocean were spectacular from the well appointed home. There’s no need to leave the property as there are toys and entertainment for everyone. The property manager and owner were very responsive to any concerns that arose. I highly recommend this property. It’s one of kind!

5.0 / 5.0

Mar 2024

We had a wonderful time at Southwind! So much to do, beautiful beach, fishing, hot tub, pool, fire pit, pickle ball, mini golf course…it kept our grand children so busy, they never complained of boredom! Everything is so close by…grocery stores, restaurants and shopping! Definitely a piece of heaven!

5.0 / 5.0

Mar 2024

Better then the pictures show. Awesome for our family of 10. So much to do. Great place.

5.0 / 5.0

Mar 2024

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.

5.0 / 5.0

Feb 2024

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

5.0 / 5.0

Jan 2024

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!

5.0 / 5.0

Dec 2023

Southwind has always been the perfect house for my family. There is plenty of room for everyone. All of the amenities allow us to stay at the house and never leave. It’s the perfect place for everyone to relax and spend quality time together.

5.0 / 5.0

Oct 2023

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!!

5.0 / 5.0

Oct 2023

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!

5.0 / 5.0

Jul 2023

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.

5.0 / 5.0

Apr 2023

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

5.0 / 5.0

Apr 2023

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!

5.0 / 5.0

Feb 2023

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!

5.0 / 5.0

Feb 2023

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!

5.0 / 5.0

Jan 2023

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!!

5.0 / 5.0

Dec 2022

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.

5.0 / 5.0

Nov 2022

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.

5.0 / 5.0

Oct 2022

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

5.0 / 5.0

Oct 2022

Incredible property and home! Beautiful!

5.0 / 5.0

Jun 2022

Amazing Property

Amazing Property

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!!

5.0 / 5.0

Jun 2022

Girls vacation

Girls vacation

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!

5.0 / 5.0

May 2022

Paradise in the Keys

Paradise in the Keys

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.

5.0 / 5.0

May 2022

Three week rental with family

Three week rental with family

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

5.0 / 5.0

Apr 2022

Heaven

Heaven

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

5.0 / 5.0

Mar 2022

Amazing

Amazing

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!

5.0 / 5.0

Mar 2022

AMAZING!!

AMAZING!!

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!

5.0 / 5.0

Mar 2022

Your Own Private Resort

Your Own Private Resort

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.

5.0 / 5.0

Feb 2022

Awesome Beach House!

Awesome Beach House!

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!

5.0 / 5.0

Feb 2022

This property exceeded our expectations.

This property exceeded our expectations.

Easy if available.

5.0 / 5.0

Jan 2022

Beautiful home

Beautiful home

This home was perfect for our fun family vacation!

5.0 / 5.0

Jan 2022

Gorgeous Oceanfront Home with Private Beach

Gorgeous Oceanfront Home with Private Beach

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.

5.0 / 5.0

Jan 2022

Paradise with privacy

Paradise with privacy

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

5.0 / 5.0

Jan 2022

A fantastic house in a beautiful location

A fantastic house in a beautiful location

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!

5.0 / 5.0

Jan 2022

Beautiful Islamorada home

Beautiful Islamorada home

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

5.0 / 5.0

Dec 2021

Southwind

Southwind

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.

FAQs

How much does this house cost compared to others in Lower Matecumbe Key?

The average price for a rental in Lower Matecumbe Key is £349 per night. This rental is £1,554 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Stunning Oceanfront Home located in Islamorada Florida. 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 Stunning Oceanfront Home located in Islamorada Florida. Enjoy the water!

Is Stunning Oceanfront Home located in Islamorada Florida pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Stunning Oceanfront Home located in Islamorada Florida?

We found 13 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen or kitchenette, and internet / wifi.

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Indulge in a peaceful retreat at Caloosa Cove Resort, our elegant Hotel in Lower Matecumbe Key. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

££££

Stunning Oceanfront Home located in Islamorada Florida

House in Lower Matecumbe Key, FL

Reasons to book

About this house rental

Amenities

Map of Lower Matecumbe Key, FL

Nearby attractions

Stunning Oceanfront Home located in Islamorada Florida

House in Lower Matecumbe Key, FL

Reasons to book

About this house rental

Amenities

Map of Lower Matecumbe Key, FL

Nearby attractions

Ratings and reviews

FAQs

How much does this house cost compared to others in Lower Matecumbe Key?

Is parking included with this house?

Is there a pool at this house?

Is Stunning Oceanfront Home located in Islamorada Florida pet friendly?

What amenities are available at Stunning Oceanfront Home located in Islamorada Florida?

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