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Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier

Photo gallery for Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier

A couple relaxing on a sun lounger with a view of the ocean and palm trees. - Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier (Islamorada)
Relaxing beach chairs - Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier (Islamorada)
Kitchen from the dining room - Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier (Islamorada)
A resort with a swimming pool, lounge chairs, and a view of the ocean. - Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier (Islamorada)
A spacious living room with a large TV, a ceiling fan, and a view of the ocean. - Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier (Islamorada)
At Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier, you can look forward to a firepit, a garden, and a playground. This vacation home is a great place to bask in the sun with a beachfront location and sun loungers. For some rest and relaxation, visit the hot tub. In addition to an arcade/game room and laundry facilities, guests can connect to free in-room WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices).

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms7 bathrooms4000 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer

Add dates for prices

About this property

Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier

  • Welcome to a private beachfront estate in on the Atlantic ocean in Islamorada where refined comfort meets the ease of a luxury resort. With 5 bedrooms and 6.5 bathrooms, this spectacular property is exceptionally well suited for couples traveling together, family celebrations, and multigenerational getaways. Set across beautifully designed resort-style grounds, the home offers an elevated vacation experience with standout amenities including a private fishing pier, pickleball, mini golf, basketball shooting, ping pong, kayaks, and bikes. From sun-soaked days by the pool to peaceful mornings on the water and effortless evenings gathered with family and friends, every detail is designed to deliver the space, privacy, and lifestyle that make a Florida Keys stay truly unforgettable.Questions before booking? Message us through Vrbo before submitting a reservation request—no booking request or payment is required. We usually respond within four hours.

Property amenities

Beach

  • On the beach
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car recommended
  • Wheelchair-accessible parking available

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 6.5 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Music library
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Firepit
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 on-site accessible parking spaces
  • Upper floors accessible by stairs only
  • Wheelchair-accessible parking
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Gym
  • Heated pool
  • Kayak
  • Outdoor pickleball court
  • Table tennis
  • Tennis
  • Water sports equipment
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

General

  • Bicycles
  • Garden
  • Unit size: 4,000 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Take out the trash
Lock the doors
Failure to complete these may result in a negative review from the host.

Rules

Guest is required to sign a Renter Agreement. Security Deposit Required of up to $1000. Minimum age to rent is 25.
Renter Agreement must be signed within 48hrs after booking. For last-minute reservations, agreement must be signed before check-in info will be sent.
NO Smoking. Pets allowed with fee. NO parties/events. Quiet Hours are from 10:00 PM - 7 AM.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total pets
Note from host: Only dogs allowed.

Children and extra beds

Children are welcome

Events

No events allowed

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have elevators
A car is recommended for transportation to and from this property

About the area

Located on the beach, this vacation home is in Matecumbe, a neighborhood in Islamorada. Keys History & Discovery Center and History of Diving Museum are cultural highlights, and some of the area's landmarks include Indian Key Historic State Park and Hurricane Monument. Consider Lorelei Restaurant & Cabana Bar for a night out or MoradaWay Arts & Cultural District if you're traveling with kids. Discover the area's water adventures with jet skiing, kayaking, and scuba diving nearby, or enjoy the great outdoors with ecotours. Visit our Islamorada travel guide
View more Vacation homes in Islamorada
Map
Islamorada, FL

What's nearby

  • A wooden deck with benches overlooking a clear blue sea.
    Anne's Beach
    3 min drive - 4.6 km
  • A mangrove tree with roots in shallow water.
    Indian Key Historic State Park
    4 min drive - 4.4 km
  • A marina with boats docked, a motel, and a cafe.
    Bud n' Mary's Dive Center
    6 min drive - 8.3 km
  • Sunset Drive Beach
    2 min drive - 2.7 km
  • Robbie’s of Islamorada
    3 min drive - 3.4 km

Getting around

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

Restaurants

  • Hungry Tarpon Restaurant
    2 min drive
  • Lorelei Restaurant & Cabana Bar
    9 min drive
  • Habanos Oceanfront Dining
    3 min drive
  • Lazy Days Restaurant
    5 min drive
  • Papa Joe’s Waterfront
    5 min drive

Frequently asked questions

Does Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier have a pool?

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

Is Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier pet-friendly?

Yes, this property allows dogs (limit 1 total).

How much is parking?

Onsite parking is available at the property.

What time is check-in at Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier?

Check-in begins at 4:00 PM.

What time is check-out at Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier?

Check-out is at 10:00 AM.

Where is Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier located?

Nestled on the beach, this Matecumbe vacation home is within 3 mi (5 km) of Sunset Drive Beach, Anne's Beach, and Robbie’s of Islamorada. Indian Key Historic State Park is 2 mi (3.2 km) away.

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Reviews

Southwind Private Beachfront Estate with Infinity Pool, Spa and Fishing Pier Reviews

10

Exceptional

9.8

Cleanliness

9.8

Location
Rating 10 - Excellent. 77 out of 81 reviews
Rating 8 - Good. 4 out of 81 reviews
Rating 6 - Okay. 0 out of 81 reviews
Rating 4 - Poor. 0 out of 81 reviews
Rating 2 - Terrible. 0 out of 81 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pool / spa was fantastic. Great views, felt private. House was better than the pictures. We really had an enjoyable family week.
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Everything was excellent!

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

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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