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Private Beachfront Estate with Resort-Style Pool & Pier

Photo gallery for Private Beachfront Estate with Resort-Style Pool & Pier

Exterior
Exterior
Sports court
Sports court
Exterior

Reviews

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

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Rooms & beds

5 bedrooms (sleeps 10)

Main Level Bunkroom Garden View

1 Single Bunk Bed and 2 Single Beds

Main Level Guest Suite

1 Queen Bed

Primary Suite - Oceanfront

1 King Bed

Upper Guest Garden View

2 Double Futons and 2 Single Beds

Upper Level Ensuite Oceanfront

1 Queen Bed

6 bathrooms, 1 half bathroom

Bunkroom Ensuite Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Lower Guestroom Ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Lower Suite - Ensuite Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Main House Powder Room

Soap · Toilet

Pool Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Primary Bathroom - Ensuite

Soap · Towels provided · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Upper Suite - Ensuite bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Dining area

About this property

Private Beachfront Estate with Resort-Style Pool & Pier

Welcome to a private beachfront estate on the ocean side 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 Pop a Shot, ping pong, kayaks, bikes and so much more. 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.

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House Rules

Check in after 4:00 PM

Minimum age to rent: 25

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 (limit 1 total)

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Smoking

Smoking is not permitted

Important information

You need to know

Property # 5253841vb
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Islamorada

Matecumbe, a neighbourhood in Islamorada, is home to this holiday home. 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.
View more Holiday homes in IslamoradaOpens in a new window
Map
Islamorada, FL

What's nearby

  • Sunset Drive Beach - 2 min drive - 2.7 km
  • Robbie’s of Islamorada - 3 min drive - 3.4 km
  • Anne's Beach - 3 min drive - 4.6 km
  • Bud n' Mary's Dive Center - 6 min drive - 8.3 km
  • Florida Keys Brewing Co. - 9 min drive - 11.7 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
  • ‪Lorelei Restaurant & Cabana Bar - ‬9 min drive
  • ‪Papa Joe’s Waterfront - ‬5 min drive
  • ‪Islamorada Fish Company - ‬7 min drive

Frequently asked questions

Does Private Beachfront Estate with Resort-Style Pool & Pier have a pool?

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

How much does it cost to stay at Private Beachfront Estate with Resort-Style Pool & Pier?

As of 19 May 2026, prices found for a 1-night stay for 2 adults at Private Beachfront Estate with Resort-Style Pool & Pier on 28 May 2026 start from AU$3,047, 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 Private Beachfront Estate with Resort-Style Pool & Pier pet-friendly?

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

How much is parking at Private Beachfront Estate with Resort-Style Pool & Pier?

On-site parking is available at the property.

What time is check-in at Private Beachfront Estate with Resort-Style Pool & Pier?

Check-in begins at 4:00 PM.

What time is check-out at Private Beachfront Estate with Resort-Style Pool & Pier?

Checkout is at 11:00 AM.

Where is Private Beachfront Estate with Resort-Style Pool & Pier located?

This family-friendly Islamorada holiday home is located in Matecumbe, within 2 mi (3 km) of Sunset Drive Beach and Robbie’s of Islamorada. Indian Key Historic State Park and Anne's Beach are also within 3 miles (5 km).

Reviews

10

Exceptional

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

Paul F.

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

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

David G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was spectacular. Very private, with stunning views. Michael and Mike were very easy to work with and responsive, loved the in-person checkin to ensure we got settled okay. Great fishing on the dock!
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

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

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

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
Response from VrboOwner on 10 Mar 2025
Thank you so much.
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

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

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

Ken P.

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

Gorgeous property!

Beautiful ocean views, lovely outdoor eating area, fabulous pool and hot tub overlooking the beach, well-stocked kitchen. We enjoyed every minute of our stay here!
Stayed 7 nights in May 2021
Verified

10/10 Excellent

Linda O.

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

Beautiful home

This home was perfect for our fun family vacation!
Stayed 7 nights in Jan 2022
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

10/10 Excellent

Jeanne A.

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

Beautiful Islamorada home

This property is beautiful and very spacious. It was excellent for a multi generational family holiday reunion.
Stayed 7 nights in Dec 2021
Verified

10/10 Excellent

Ben R.

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

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!
Stayed 7 nights in Feb 2022
Verified

10/10 Excellent

Jayne S.

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

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.
Stayed 7 nights in May 2022
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

Amy B.

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

Immaculate home!!

Immaculate beachfront home with amazing views! We had a party of 8 (4 couples) and it was more than enough room! Loved the amenities and location!! We would definitely stay here again!
Stayed 7 nights in Apr 2021

About the host

Hosted by Cari Castaneda

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