Condo

Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views

Photo gallery for Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views

A spacious living room with a dining area, large windows with a view, and a ceiling fan.
A marina with boats docked, a clear blue sky, and a view of the ocean.
A multi-story hotel with balconies, palm trees, and a paved driveway.
A swimming pool with lounge chairs and palm trees, surrounded by a fence and a building in the background.
A tennis court with a pool, surrounded by buildings and palm trees.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Laundry made easy
    One of the few properties with an in-unit washing machine and dryer.
  • Discover nearby landmarks
    Close to Sunset Drive Beach

Popular amenities

  • Balcony or patio
  • Spa pool on site
  • Swimming pool
  • Gas barbecue
  • Internet access
  • Washer/dryer

Explore the area

View map
Islamorada, FL
  • Place, Sunset Drive Beach
    ‪5 min walk‬
  • Place, Anne's Beach
    ‪2 min drive‬
  • Place, Robbie’s of Islamorada
    ‪5 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪34 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Bidet · Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Half Bathroom 3

Toilet

Spaces

Porch or lanai
Kitchen
Balcony
Separate dining area
Dining area

Add dates for prices

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About the area

Islamorada

Matecumbe, a neighbourhood in Islamorada, is home to this condo. 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. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven.
Map
Islamorada, FL

What's nearby

  • Sunset Drive Beach - 5 min walk - 0.4 km
  • Anne's Beach - 2 min drive - 2.1 km
  • Robbie’s of Islamorada - 5 min drive - 6.3 km
  • Bud n' Mary's Dive Center - 9 min drive - 11.3 km
  • Florida Keys Brewing Co. - 12 min drive - 14.6 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 29 min drive

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬5 min drive
  • ‪Habanos Oceanfront Dining - ‬16 min walk
  • ‪Lazy Days Restaurant - ‬7 min drive
  • ‪Papa Joe’s Waterfront - ‬7 min drive
  • ‪Tiki Bar at Amara Cay Resort - ‬8 min drive

Frequently asked questions

Does Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views have a pool?

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

How much does it cost to stay at Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views?

As of 6 Nov 2026, prices found for a 1-night stay for 2 adults at Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views on 7 Nov 2026 start from AU$5,473, 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 Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views?

Check-in begins at 3:00 PM.

What time is check-out at Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views?

Checkout is at 10:00 AM.

Where is Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views located?

Located in Matecumbe, this condo building is within 1 mile (2 km) of Sunset Drive Beach and Anne's Beach. San Pedro Underwater Archaeological Preserve State Park is 2.2 mi (3.5 km) away.

Reviews

9.8

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. 19 out of 21 reviews
Rating 8 - Good. 1 out of 21 reviews
Rating 6 - Okay. 0 out of 21 reviews
Rating 4 - Poor. 1 out of 21 reviews
Rating 2 - Terrible. 0 out of 21 reviews

9.4/10

Cleanliness

9.6/10

Check-in

9.4/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and condo is very nice. Plenty of space for a big family. Marina is also very nice.
Stayed 13 nights in Dec 2025
Verified review

10/10 Excellent

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

Great views, comfortable home.

Comfortable and well appointed. We'd stay again.
Stayed 7 nights in Apr 2022
Response from VrboOwner on 20 May 2022
And we hope you do too!!! SO glad y'all had a wonderful vacation! See you again soon! Sincerely, Freewheeler Vacations Team
Verified review

10/10 Excellent

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

Beautiful condo and property!

The condo was just beautiful and well decorated and stocked. All the amenities were amazing. Pool , hot tub , boat docking was perfect. We had a wonderful week. Close to all restaurants and shopping. Thank you and we will be back.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 11 July 2022
Thank you SO much for the awesome review. We enjoyed having you as our guest and hope you come back soon. Tight Lines, The Freewheeler Vacations Team
Verified review

10/10 Excellent

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

Beautiful, great location, perfect condo!

We come to Islamorada every year as a family & this is one of the best places we’ve stayed! The location was absolutely perfect! The condo was clean, beautifully decorated, & the views were amazing! The management company was easy to work with, the AC went out while we were there & they had someone there to fix it in a couple hours. We really enjoyed this property & can’t wait for next year!
Stayed 7 nights in Jul 2022
Response from VrboOwner on 22 Aug 2022
Thank you so much for your wonderful review. Like at your own home, things happen. Our job is to JUMP on them as quickly as possible and keep you in cool air! We hope to see you back again real soon! Tight Lines! The Freewheeler Vacations Team
Verified review

10/10 Excellent

Bay Harbour A304

The condo is very well appointed with high end appliances and comfy furniture on the screen porch. The grounds are beautiful with lush foliage and the grounds and pool are very clean and very well maintained.
Stayed 10 nights in Oct 2018
Verified review

10/10 Excellent

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

Amazing week - Amazing property

This was the perfect property for our family to vacation in Islamorada. The view from the third floor was my favorite part! I spent most of my time on the lanai when we weren’t boating, fishing, snorkeling or out enjoying restaurants and shopping. Kitchen was fully equipped and the condo was beautifully decorated. This did not feel like a rental property but felt like a home I would live in. We brought our boat and it was in the backyard with quick access to the Gulf. Gas dock and bait shop were right across from the dock. The complex was very quiet. We had the pool to ourselves most days after we boated. We hope to return in the future and highly recommend this property.
Stayed 8 nights in Apr 2022
Response from VrboOwner on 8 June 2022
Thank you SO much for your kind review. We think this condo is a very special place as well. Hope to see you and your family back again very soon! Sincerely, Freewheeler Vacations Team
Verified review

10/10 Excellent

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

Loved property and owner. Free wheelers not so much.

We arrived Saturday evening and it was amazing. This condo has been upgraded since the photos and it gorgeous! Amazing location too! The owner actual stopped by Sunday morning because they dropped off some extra towels. He was the sweetest person. Free wheelers on the other hand was difficult. They needed the washer looked at, and called me a few times to setup times but the tech never showed. So we were unable to wash items such a towels. Then I emailed about games and coffee maker and they didn’t know the answer but the owner told us so we got it figured out. So all in all amazing review, just not a fan of free wheelers.
Stayed 7 nights in May 2022
Response from VrboOwner on 11 June 2022
Thank you for your review. Good or bad, we appreciate them all, helps us to do our job better! However, in this instance, I think we need to add a little response to the review. The appliance man DID show up as promised, just while the guest was not there. A part was ordered, took a hot minute to be delivered, and dryer did get fixed. Like at your own home, things sometimes break. (Which is why extra towels were dropped off so that you were not inconvenienced!) It's our job to jump on issues and deal with them as fast as possible while making things good when that takes a while. Which is exactly what we did. :-) Hope to see you back again soon! Tight Lines, The Freewheeler Vacations Team
Verified review

10/10 Excellent

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

Great Vacation

Bay Harbour is a great place to stay
Stayed 30 nights in Mar 2022
Response from VrboOwner on 27 May 2022
Thank you so much for your wonderful review Suzanne! Hope to see you again soon! Freewheeler Vacations Team
Verified review

10/10 Excellent

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

paradise!

A lovely, well maintained property! This unit seems to have been updated even more since the pictures were taken. It is huge and has room for everyone. Well stocked kitchen if you want to cook, but so many great restaurants we did not! Pool is heated and has lots of chairs. will definitely go back!
Stayed 7 nights in Jan 2022
Verified review

10/10 Excellent

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

Beautiful condo in a great location

Absolutely loved the condo and the location was exactly what we were looking for. Morning sunrises we’re spectacular and the moonrises over the harbor were a nightly sensation. Kitchen could use some more forks and a larger skillet. Should also fix the washer.
Stayed 8 nights in Dec 2021
Verified review

10/10 Excellent

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

Superior

No surprises , clean, beautiful view. Plan to return next year!!
Stayed 7 nights in Jul 2021
Verified review

10/10 Excellent

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

Family Week in Islamorada Florida

I found this property on VRBO. As this was our first experience with VRBO we were not sure what to expect. Our consultant with Freelance, Brandi, was excellent. She advised that the property looked exactly like the pictures. It was amazing, the property and view.
Stayed 7 nights in Jul 2021
Verified review

8/10 Good

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

lovely place!

We loved it! very clean, nice pool, sleeping arrangements. We didn't have a boat, but shared with families who did! Will go back soon!
Verified review

10/10 Excellent

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

Great unit with super view

Had a wonderful time. The unit has everything and is very nice. . Great location Too. Highly recommend.
Stayed 7 nights in Mar 2021
Verified review

10/10 Excellent

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

Fantastic Accommodations

We were so pleasantly surprised when we walked through the front door at the view and then how beautifully decorated the home was. First class furnishings and appliances. The split bedroom plan afforded plenty of privacy. Particularly appreciated the convenience of having our boat directly below our condo in a safe and quiet harbor. Fuel dock is right nextdoor. Covered parking was a gift. Very well maintained community. We will definitely visit again.
Stayed 7 nights in Mar 2021
Verified review

10/10 Excellent

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

First time stay was fantastic!!

This was our first time stay in Islamorada and we absolutely loved it! The condo had fantastic appliances and fully stocked. The view was beautiful and quiet. Can’t wait to come visit again!
Stayed 14 nights in Feb 2021
Verified review

10/10 Excellent

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

Great family vacation

Great place to stay. Good location.
Stayed 7 nights in Dec 2020
Verified review

10/10 Excellent

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

Islamorada

Great property, very clean. Also, the boat access and docking were perfect.
Stayed 8 nights in Jul 2020
Verified review

4/10 Poor

Liked: Location
Disliked: Cleanliness, check-in, communication

Very cheap and very poorly set up

The property is fine. The issues were with the rental agents and the property owners. Hey we all are trying to be cost effective in our lives and our management of our things. This unit is cheaply managed. I was stunned when the retail agent finally informed me that the unit had been cleaned the day I arrived. The guest bathroom had soap scum and mold on the shower curtain. My friend who came down for a bit of fun in the sun and used that bathroom was not happy. She has an illness mold doesn't help. The unit was not set up. There was very little toilet paper for the 2 1/2 bathrooms. And there was about an eight of a roll of paper towels on the kitchen counter. THERE WAS NO FOLDER ABOUT THE UNIT ON THE PROPERTY. The rental agent was impossible to deal with. I called and unless one particular person was there or they called there was no communication. They never called back. The refrigerator needs a new water filter. I said to the rental agency before I arrived that I am allergic to all things Tyde it doesn't matter what type. I open the washer and dry cabinet and guess what there is the Tyde. So at 8pm I am washing the linens and towels. Until my friend arrived a good deal of the bedding was on the floor. I have wear gloves. My family was set come while I was there. Now the arrival. I received the arrival info as I was driving to the location. I arrive about 4pm. And after beaning at the gate someone tells me the code so they can get in. One of the ladies at the pool was very helpful. I was expecting the rental agent to be there no. So there I am talking with owners of their units and there was no one there. I who had been driving for hours looked at my phone because one of the pool group asked who was the rental agent. So I scrolled threw my email on the phone and there was the entry instructions. Well the head of the association let me in. See I had a very expensive musical instrument in my vehicle and I had to get it out because of the temp. In fact the he helped me unload the car. The people at the property were very nice and very helpful. Once I got in and looked at my computer I could really read the entry instructions. I had to drive to their office to a lock box. If you have never been to the keys, driving at 5ish isn't fun or easy. I want a refund. It wasn't fun. There is no sunlight in the unit. I moved on. I can say more and will to the Town and State. Some Vacation.
Verified review

10/10 Excellent

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

Amazing week

We had the most amazing week in Islamorada! We had three adults and two kids in the rental and it was perfect. This condo is incredible. It is clean and they have great appliances. It’s a quiet area with a great pool. Very relaxing! We will be back 😊
Stayed 7 nights in Dec 2019
Verified review

10/10 Excellent

Bay Harbour Paradise

Great facility and would definitely return and/or recommend to others.
Stayed 10 nights in Mar 2018
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