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Stunning Oceanfront Home located in Islamorada Florida

Photo gallery for Stunning Oceanfront Home located in Islamorada Florida

Beach
Exterior
Exterior
Dining
Dining and living room

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms6+ bathroomsSleeps 104200 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Lower Metecumbe, FL
  • Place, Sunset Drive Beach
    ‪3 min drive‬
  • Place, Anne's Beach
    ‪4 min drive‬
  • Place, Bud n' Mary's Dive Center
    ‪7 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪40 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 Twin Bunk Bed and 2 Twin Beds

Master

1 King Bed

Upper guest bedroom

2 Double Futons and 2 Twin 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

Stunning Oceanfront Home located in Islamorada Florida

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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 35
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 50 lbs per pet (limit one pet total)
Dogs 25 lbs or less
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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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Islamorada

Located in Matecumbe, a neighborhood in Islamorada, this vacation 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 Keys History & Discovery Center and History of Diving Museum are cultural highlights. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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Map
Lower Metecumbe, FL

What's nearby

  • Sunset Drive Beach - 3 min drive - 2.7 km
  • Lower Matecumbe Beach - 3 min drive - 2.7 km
  • Robbie’s of Islamorada - 3 min drive - 3.0 km
  • Anne's Beach - 4 min drive - 4.6 km
  • Bud n' Mary's Dive Center - 7 min drive - 8.0 km

Getting around

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

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬2 min drive
  • ‪Lazy Days Restaurant - ‬5 min drive
  • ‪Papa Joe’s Waterfront - ‬5 min drive
  • ‪Lorelei Restaurant & Cabana Bar - ‬9 min drive
  • ‪Islamorada Fish Company - ‬7 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.

How much does it cost to stay at Stunning Oceanfront Home located in Islamorada Florida?

As of Apr 4, 2026, prices found for a 1-night stay for 2 adults at Stunning Oceanfront Home located in Islamorada Florida on May 13, 2026 start from $2,088, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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 50 lbs per pet.

How much is parking?

Onsite parking is available at the property.

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?

Check-out is at 11:00 AM.

Where is Stunning Oceanfront Home located in Islamorada Florida located?

Nestled on the beach, this Matecumbe vacation 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 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 73 out of 77 reviews
Rating 8 - Good. 4 out of 77 reviews
Rating 6 - Okay. 0 out of 77 reviews
Rating 4 - Poor. 0 out of 77 reviews
Rating 2 - Terrible. 0 out of 77 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Kristie D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing trip! Amazing location. It was a wonderful week and we would stay there again in an instant. It hit all the right notes, thank you!
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Michelle G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great time ! Thank you
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Vincent M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property and property management.
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Shirley S W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property equipped with everything we needed. A nice, peaceful week enjoyed by all!
Sunrise at Southwind.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

D C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Michael was very friendly and helpful. Well maintained home with a beautiful view
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

DAWN D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Okie M.

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

Great location and great house

House is perfect for a family vacation. Amenities are fantastic.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Tiffany Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jan 2026
Verified

10/10 Excellent

Franck K.

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
Verified

10/10 Excellent

Chris P.

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

Everything was excellent!

The view is amazing!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

James D.

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
Verified

10/10 Excellent

Michael R.

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

Stunning inside and out

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.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Jana P.

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
Verified

8/10 Good

gregg h.

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
Verified

10/10 Excellent

Matthew H.

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

Amazing Property and Location

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!
Stayed 7 nights in Feb 2023
Verified

8/10 Good

gregg h.

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

Vacation in the keys

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.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Bryan H.

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
Verified

10/10 Excellent

Jeff M.

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
Verified

10/10 Excellent

Holli H.

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

Islamorada slice of heaven

Coming from Montana and Seattle, we were looking forward to some sun and relaxation in the Florida Keys. Southwind gave us this in terrific style, and so much more!
Stayed 7 nights in Jan 2021
Verified

10/10 Excellent

Alexis S.

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
Verified

10/10 Excellent

Mb P.

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
Verified

10/10 Excellent

Josh B.

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
Verified

10/10 Excellent

Kimberly J.

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
Verified

8/10 Good

Peter G.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Wonderful

Some small details but overall a very enjoyable stay. I would return.
Stayed 7 nights in Sep 2021
Verified

10/10 Excellent

Alexis V.

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

About the host

Hosted by Michael Ivancevic

Host profile image
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

Premier Host

They consistently provide great experiences for their guests
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