Stunning Oceanfront Home located in Islamorada Florida

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Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms6+ bathroomsSleeps 10390.2 sq m

Popular amenities

Beach view
Parking available
Pet-friendly
Dryer

Explore the area

Lower Metecumbe, FL

Sunset Drive Beach
‪1 min walk‬
Anne's Beach
‪3 min drive‬
Bud n' Mary's Dive Center
‪5 min drive‬
Marathon, FL (MTH-Florida Keys Marathon)
‪30 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Guest with ocean view

1 Queen Bed

Lower Guest bedroom

1 King Bed

Lower guest room

1 Single Bunk Bed and 2 Single Beds

Master

1 King Bed

Upper guest bedroom

2 Double Futons and 2 Single Beds

6 bathrooms, 1 half bathroom

Half bath

Toilet

Kids room

Bathtub or shower · Toilet

Lower guest

Toilet · Shower only

Lower guest room

Toilet · Shower only

master

Bathtub · Toilet · Shower only

Pool bath

Bathtub or shower · Toilet

Upper Guest bath

Toilet · Shower only

Spaces

Deck or patio

Porch or lanai

Kitchen

Balcony

Separate dining area

Outdoor play area

Garden

Dining area

About this property

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.

Property manager

Michael Ivancevic

Languages

English

Add dates for prices

Amenities

Pool

Hot tub

Kitchen

Washer

Dryer

Pet-friendly

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Ocean view
Pool
Kitchen
Washer

House Rules

Check in after 4:00 PM

Minimum age to rent: 35

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs less than 23 kg per pet (limit one pet total)

Dogs 25 lbs or less

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

On-site parties or group events are strictly prohibited

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is required for transport to and from this property

About the area

Islamorada

Located in Matecumbe, a neighbourhood in Islamorada, this holiday home is near theme parks and on the beach. The area's natural beauty can be seen at San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park, while MoradaWay Arts & Cultural District and Keys History & Discovery Center are cultural highlights. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Lower Metecumbe, FL

What's nearby

Sunset Drive Beach - 1 min walk - 0.0 km
Robbie’s of Islamorada - 2 min drive - 2.8 km
Indian Key Historic State Park - 3 min drive - 3.4 km
Anne's Beach - 3 min drive - 3.8 km
Bud n' Mary's Dive Center - 5 min drive - 6.4 km

Getting around

Marathon, FL (MTH-Florida Keys Marathon) - 30 min drive

Restaurants

‪Robbie's of Islamorada - ‬2 min drive
‪Lorelei Restaurant & Cabana Bar - ‬9 min drive
‪Lazy Days Restaurant - ‬5 min drive
‪Islamorada Fish Company - ‬7 min drive
‪Square Grouper - ‬6 min drive

Frequently asked questions

Does Stunning Oceanfront Home located in Islamorada Florida have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Stunning Oceanfront Home located in Islamorada Florida pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at Stunning Oceanfront Home located in Islamorada Florida?

Check-in begins at 4:00 PM.

What time is check-out at Stunning Oceanfront Home located in Islamorada Florida?

Checkout is at 11:00 AM.

Where is Stunning Oceanfront Home located in Islamorada Florida located?

Nestled on the beach, this Matecumbe holiday home is within a 15-minute walk of Sunset Drive Beach and San Pedro Underwater Archaeological Preserve State Park. Anne's Beach and Robbie’s of Islamorada are also within 3 miles (5 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Matt F.

27 March 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Property! Pictures Don't Do Justice!

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!

Stayed 7 nights in Mar 2025

10/10 Excellent

Kim J.

19 March 2025

Liked: Check-in, communication, location, listing accuracy

Family Vacation

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

Stayed 7 nights in Mar 2025

10/10 Excellent

Chris P.

18 March 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Everything was excellent!

The view is amazing!

Stayed 7 nights in Mar 2025

10/10 Excellent

Franck K.

9 March 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Property in Islamorada

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.

Stayed 7 nights in Feb 2025

10/10 Excellent

Jeff M.

4 January 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

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.

Stayed 7 nights in Dec 2024

10/10 Excellent

Sheila H.

30 December 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Christmas 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.

Stayed 7 nights in Dec 2024

10/10 Excellent

Alexis S.

3 December 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Southwind

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

Stayed 7 nights in Nov 2024

10/10 Excellent

Bryan H.

17 September 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Time

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.

Stayed 7 nights in Sep 2024

8/10 Good

gregg h.

23 June 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property

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.

Stayed 7 nights in Jun 2024

10/10 Excellent

Lauren S.

2 June 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Heaven on earth!

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!

Stayed 7 nights in May 2024

10/10 Excellent

Rachel W.

30 April 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

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!

Stayed 7 nights in Apr 2024

8/10 Good

Katie W.

26 April 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Islamorada Getaway

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!

Stayed 10 nights in Apr 2024

10/10 Excellent

Kara C.

10 April 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing View

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!

Stayed 7 nights in Mar 2024

10/10 Excellent

Sue M., Northern Virginia

31 March 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Something for everyone!

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!

Stayed 7 nights in Mar 2024

10/10 Excellent

Kimberly J.

21 March 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Piece of Heaven at Southwind!

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!

Stayed 7 nights in Mar 2024

10/10 Excellent

Mb P.

10 March 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vac

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

Stayed 7 nights in Mar 2024

10/10 Excellent

Jana P.

4 March 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home

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.

Stayed 7 nights in Feb 2024

10/10 Excellent

James D.

11 February 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful family stay at Southwind

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

Stayed 10 nights in Feb 2024

10/10 Excellent

Julie F.

31 January 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Southwind

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!

Stayed 17 nights in Jan 2024

10/10 Excellent

sunny s.

30 December 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sunny

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.

Stayed 14 nights in Dec 2023

10/10 Excellent

Alexis V.

30 October 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise Found

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!!

Stayed 7 nights in Oct 2023

10/10 Excellent

Philip H.

17 October 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Islamorada Southwind Review

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!

Stayed 7 nights in Oct 2023

10/10 Excellent

Linda F.

4 July 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time

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.

Stayed 10 nights in Jun 2023

10/10 Excellent

Josh B.

2 April 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Property

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

Stayed 7 nights in Mar 2023

10/10 Excellent

Michele H.

1 April 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

All You Need!

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!

Stayed 14 nights in Mar 2023

About the host

Hosted by Michael Ivancevic

We are a family that lives in Palm Beach county that fell in love with Islamorada over 40 years ago. We have enjoyed this slice of paradise and we hope you do too.

Why they chose this property

Privacy and high end home is what this property is all about. It will provide an amazing experience and make lifetime memories for you and your family. Gorgeous infinity edge pool overlooking the beach and ocean. Enjoy the 185' dock to fish, snorkel, paddle board, and the stunning sunrises and sunsets. The property is called southwind and upon arrival you can't help but notice the smooth ocean breeze coming off the ocean from the southerly direction.

What makes this property unique

Don't be afraid to try and catch a tarpon or bonefish from the dock. We provide bikes, paddle boards, kayaks, mooring buoy for your boat, pingpong table, pop a shot, and hammocks hanging from the palm tree's.

Languages:

English

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Stunning Oceanfront Home located in Islamorada Florida

Photo gallery for Stunning Oceanfront Home located in Islamorada Florida

Reviews

Popular amenities

Explore the area

Rooms & beds

5 bedrooms (sleeps 10)

Guest with ocean view

Lower Guest bedroom

Lower guest room

Master

Upper guest bedroom

6 bathrooms, 1 half bathroom

Half bath

Kids room

Lower guest

Lower guest room

master

Pool bath

Upper Guest bath

Spaces

About this property