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Private Beachfront Estate with Resort-Style Pool & Pier

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

A room with a wooden ceiling, large windows with a beach view, wicker furniture, and a glass coffee table.
A beachfront property with a large house, tennis courts, and palm trees.
A bedroom with a bed, a balcony with a view of the ocean, and a chair.
NEW PHOTOS COMING SOON
A resort with a swimming pool, lounge chairs, and a view of the ocean.

Reviews

10 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Pickleball on-site
    A rare find — enjoy pickleball without leaving the property.
5 bedrooms6+ bathroomsSleeps 14

Popular amenities

  • On beach
  • Private pool
  • Hot tub on site
  • Onsite parking available
  • Dog-friendly
  • Kitchen

Explore the area

View in a map
Islamorada, FL
  • Place, Sunset Drive Beach
    ‪2 min drive‬
  • Place, Robbie’s of Islamorada
    ‪3 min drive‬
  • Place, Anne's Beach
    ‪3 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪36 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

1 - Primary Bedroom Top Level - Oceanfront with Ensuite Bath

1 King Bed

2 - Main Level Garden View Guest with Ensuite

1 King Bed

3 - Top Level Oceanfront Guest Suite - Ensuite Bathroom

1 Queen Bed

4 - Main Level Guest Suite Garden View with Bunk Beds

2 Single Bunk Beds and 2 Single Beds

5 - Top Level Guest Suite Garden View with Ensuite

3 Single Beds

6 bathrooms, 1 half bathroom

1 - Primary Suite Bathroom

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

2 - Main Level Garden View Suite Bathroom

Soap · Toilet · Shower only

3 - Top Level Oceanfront Ensuite Bath

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

4 - Main Level Garden View Suit (bunk) Bathroom

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

5 - Top Level Guest Suite Garden View Bathroom

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

6 - Main Level Powder Room

Soap · Towels provided · Toilet · Shampoo · Hair dryer

7 - Pool Bathroom - Ground level

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

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Number of living rooms
Outdoor play area
Garden

About this property

Private Beachfront Estate with Resort-Style Pool & 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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 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 2 total)
Only dogs allowed.
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Smoking

Smoking is not permitted

Check-out instructions

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

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, a first aid kit and a deadlock
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

Located on the beach, this holiday home is in Matecumbe, a neighbourhood 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 travelling with kids. Discover the area's water adventures with jet skiing, kayaking and scuba diving nearby, or enjoy the great outdoors with ecotours.
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
  • Indian Key Historic State Park - 4 min drive - 4.4 km
  • Bud n' Mary's Dive Center - 6 min drive - 8.3 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
  • ‪Lazy Days Restaurant - ‬5 min drive
  • ‪Islamorada Fish Company - ‬7 min drive
  • ‪Papa Joe’s Waterfront - ‬5 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 18 Jul, 2026, prices found for a 1-night stay for 2 adults at Private Beachfront Estate with Resort-Style Pool & Pier on 16 Oct, 2026 start from S$23,787, 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 2 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 10:00 AM.

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

Nestled on the beach, this Matecumbe holiday 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.

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. 75 out of 79 reviews
Rating 8 - Good. 4 out of 79 reviews
Rating 6 - Okay. 0 out of 79 reviews
Rating 4 - Poor. 0 out of 79 reviews
Rating 2 - Terrible. 0 out of 79 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

Rebecca D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Incredible home, perfect location, and a true luxury Florida Keys experience! The ocean views from every window are even better than you would find at a five-star resort. The linens, furnishings, and every detail throughout the home are truly high-end and absolutely beautiful. Pickleball and golf right in the front yard were enjoyed by everyone! Hands down, the best rental in the Florida Keys. We are already looking to are stay again next summer!
Stayed 7 nights in Jun 2026
Response from VrboOwner on 13 Jul, 2026
Thank you for your review, Rebecca! We are so pleased that you enjoyed your stay and hope that you will join us again next year. You were wonderful and extremely respectful guests. Enjoy the rest of your summer!
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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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
Verified

10/10 Excellent

Stephen M.

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

Oceanfront Getaway

This home is as advertised, clean, well-maintained, excellent a/c and on a beautifully maintained lot on the ocean. Very close to shops and restaurants in Islamorada and owner is very responsive.
Stayed 7 nights in Apr 2021

About the host

Hosted by Cari Castaneda

Host profile image

Why they chose this property

Perfect for multigenerational vacations, couples traveling together, and family getaways, this property offers the rare combination of privacy, space, and resort-style amenities in an unforgettable oceanfront setting. With room to gather and room to retreat, guests can enjoy quality time together while still having the comfort and flexibility that larger groups need. From the private beach and pool to the fishing pier, outdoor dining, and extensive recreation amenities, every detail is designed to make group travel easy, memorable, and distinctly special in Islamorada.

What makes this property unique

A standout feature of the accommodations is the exceptional level of privacy offered to each guest. Every bedroom includes its own private balcony and ensuite bath, creating a collection of individual retreats within the home. This thoughtful layout is ideal for multigenerational families, couples traveling together, and group getaways, offering the rare balance of shared gathering spaces and personal comfort. It’s a design that makes the home especially well suited for relaxed, elevated stays where everyone can come together with ease and still enjoy a sense of privacy.
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