House in Plantation Key, FL
10 guests · 5 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
Summary:
Experience Unparalleled Luxury at Pineapple Beach: Your Dream Getaway Awaits! Indulge in a 5-Bedroom Haven with Private Dock, Oceanfront Pool, and Endless Amenities on 3 Acres in Islamorada.
The Space:
Pineapple Beach – Private Oceanfront Estate in Islamorada
Pineapple Beach is situated on more than 3 acres in the central area of Islamorada. This exclusive 5-bedroom luxury residence is the embodiment of your dreams, offering nightly bonfires, a challenging putting green, a cabana bar, a private dock, and numerous other amenities. Get ready to pack your bags and experience a vacation that will leave an indelible mark!
If you’ve ever envisioned lounging by your own private oceanfront pool, gazing over a small beach and expansive ocean views, your dream is about to come true. This secluded, gated estate offers an unmatched level of privacy and space rarely found in the Florida Keys.
Inside, the home features a gourmet kitchen and a dining area that accommodates 10 guests, offering breathtaking views of the water. With three levels, there’s ample space for everyone to relax and unwind. Settle into the living room for movie nights on the 65” TV or challenge friends and family to a friendly foosball game.
Outdoors, indulge in your own small private beach area, complete with a fire pit, boat dock, heated pool with spa, pool bar, golf green, and abundant seating to take in the serene coastal surroundings. While the shoreline is maintained regularly, guests should note that seasonal winds and tides can bring natural sargassum seaweed to the beach. This is a normal and expected part of the coastal environment; although it is cleared periodically, it is not possible or environmentally appropriate to remove it continuously.
The main kitchen includes a full-size refrigerator, wine cooler, ice maker, two dishwashers, microwave, stove, Keurig, dual ovens, mini fridge, toaster oven, coffee maker, blender, and a 35” TV.
Exterior Amenities:
Private dock accommodating boats up to 32 feet (max draft: 36 inches, width: 12 feet)
Heated pool and spa
Pool bar and shaded seating area
Outdoor shower
Fire pit
Foosball table, cornhole, basketball hoop
Hammocks
Dedicated golf green
213-foot private beach with convenient water entry
2 kayaks and 2 paddleboards with easy launch access
Ample parking for multiple vehicles and/or boat trailer
Booking Policies
Minimum Stay:
A 7-night minimum stay is required by city regulations, with no exceptions. The city determines the maximum occupancy, and it cannot be exceeded (including adults, children, and infants).
Cancellation Policy:
We maintain a strict 60-day cancellation policy. If the cancellation is made at least 60 days before arrival, you can receive a full refund (excluding processing and admin fees). If you cancel within 60 days and we are able to rebook the same dates, you will receive a full refund minus processing and admin fees. If we are unable to secure another booking, only the deposit will be refunded.
Contract: Upon confirmation of your booking by our office, you will receive a check in form via Email/Booking Channel. Complete the form to receive further details about your stay!
Payment Options: The total reservation charges include credit card processing fees by default. We are happy to accept checks with no additional fees, and in those cases, the processing fees can be removed from your total once you confirm your preferred payment method. Credit card payments are subject to the following fees: – Visa, MasterCard, and Discover incur a 3.5% processing fee (excluding taxes and deposit) – American Express incurs an additional 0.99% fee (excluding taxes and deposit)
Guest Access:
Private gated entrance, elevator
The Neighborhood:
Located in a secluded area of Islamorada
Getting Around:
This home is about a 10 minute drive to the grocery store.
Interaction with Guests:
Check-in is private and self-guided. We won’t be there in person, but we’re available 24/7—call or text us anytime if any issues come up
Experience Unparalleled Luxury at Pineapple Beach: Your Dream Getaway Awaits! Indulge in a 5-Bedroom Haven with Private Dock, Oceanfront Pool, and Endless Amenities on 3 Acres in Islamorada.
The Space:
Pineapple Beach – Private Oceanfront Estate in Islamorada
Pineapple Beach is situated on more than 3 acres in the central area of Islamorada. This exclusive 5-bedroom luxury residence is the embodiment of your dreams, offering nightly bonfires, a challenging putting green, a cabana bar, a private dock, and numerous other amenities. Get ready to pack your bags and experience a vacation that will leave an indelible mark!
If you’ve ever envisioned lounging by your own private oceanfront pool, gazing over a small beach and expansive ocean views, your dream is about to come true. This secluded, gated estate offers an unmatched level of privacy and space rarely found in the Florida Keys.
Inside, the home features a gourmet kitchen and a dining area that accommodates 10 guests, offering breathtaking views of the water. With three levels, there’s ample space for everyone to relax and unwind. Settle into the living room for movie nights on the 65” TV or challenge friends and family to a friendly foosball game.
Outdoors, indulge in your own small private beach area, complete with a fire pit, boat dock, heated pool with spa, pool bar, golf green, and abundant seating to take in the serene coastal surroundings. While the shoreline is maintained regularly, guests should note that seasonal winds and tides can bring natural sargassum seaweed to the beach. This is a normal and expected part of the coastal environment; although it is cleared periodically, it is not possible or environmentally appropriate to remove it continuously.
The main kitchen includes a full-size refrigerator, wine cooler, ice maker, two dishwashers, microwave, stove, Keurig, dual ovens, mini fridge, toaster oven, coffee maker, blender, and a 35” TV.
Exterior Amenities:
Private dock accommodating boats up to 32 feet (max draft: 36 inches, width: 12 feet)
Heated pool and spa
Pool bar and shaded seating area
Outdoor shower
Fire pit
Foosball table, cornhole, basketball hoop
Hammocks
Dedicated golf green
213-foot private beach with convenient water entry
2 kayaks and 2 paddleboards with easy launch access
Ample parking for multiple vehicles and/or boat trailer
Booking Policies
Minimum Stay:
A 7-night minimum stay is required by city regulations, with no exceptions. The city determines the maximum occupancy, and it cannot be exceeded (including adults, children, and infants).
Cancellation Policy:
We maintain a strict 60-day cancellation policy. If the cancellation is made at least 60 days before arrival, you can receive a full refund (excluding processing and admin fees). If you cancel within 60 days and we are able to rebook the same dates, you will receive a full refund minus processing and admin fees. If we are unable to secure another booking, only the deposit will be refunded.
Contract: Upon confirmation of your booking by our office, you will receive a check in form via Email/Booking Channel. Complete the form to receive further details about your stay!
Payment Options: The total reservation charges include credit card processing fees by default. We are happy to accept checks with no additional fees, and in those cases, the processing fees can be removed from your total once you confirm your preferred payment method. Credit card payments are subject to the following fees: – Visa, MasterCard, and Discover incur a 3.5% processing fee (excluding taxes and deposit) – American Express incurs an additional 0.99% fee (excluding taxes and deposit)
Guest Access:
Private gated entrance, elevator
The Neighborhood:
Located in a secluded area of Islamorada
Getting Around:
This home is about a 10 minute drive to the grocery store.
Interaction with Guests:
Check-in is private and self-guided. We won’t be there in person, but we’re available 24/7—call or text us anytime if any issues come up
Amenities
Non-smoking
No pets allowed
Family friendly
Map of Plantation Key, FL
Ratings and reviews
10 / 10Outstanding·Jun 2026
Fantastic house and location. All the amenities you could ever ask for. The host was very responsive and immediately took care of the issues that arose.
10 / 10Outstanding·Aug 2025
Lovely house on beautiful property. We had a few issues upon arrival but the property manager was extremely helpful and responded to our issues right away. This is a great house for families of all ages and is a good location if you want to explore the entire keys.Only two things to be aware of. One is the Sargassum seaweed that the Atlantic side of the keys gets in the summer. It made it impossible to use the beach at the house or even enter the water from the property. And the smell it emits is aweful. We opted to do some water excursions from the gulf side. The other are the wild peacocks that are all over the area. Not much you can do about them as they seem to love Islamorada and regardless of the property you rent you will have to deal with them. If we decide to come back to the Keys it will be in the winter / spring months and this house would be on our list to rent again.
10 / 10Outstanding·Apr 2025
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The entire property was absolutely beautiful and the perfect place to spend Spring Break with family. We enjoyed playing cornhole and wiffle ball on the beach and spent a lot of time on the putting green. Our favorite part was the wildlife - we had many visits from the peacocks and saw manatees, stingrays, sharks and much more from the dock. We hope to visit again soon!
6 / 10Average·Jun 2025
Sadly, we feel like for the cost of the house many updates and repairs should made before renting to guests again. There was lack of communication from the property manager in regards to several items although she did mention she was having service issues. There were lack of common items such as paper towels( she said she brought these by but we did not have access to the garage to retrieve) we were also missing cleaning products and the house is in desperate need of a deep clean especially in the kitchen and the drawers of the kitchen. Once we arrived we had 2 smoke detectors beeping in which we had to go and buy batteries to replace and another smoke alarm starting beeping in the middle of the night. We also had to replace three lamps with lightbulbs, unclog the disposal from the previous guests as it was backing up the dishwasher which began to leak and flood under the sink that we had to pull everything out and clean that as well. We had one towel in each bathroom and had to search all over to finally find them in an amour downstairs. On our last day we found a book for the house that would have told us that but it was stuffed in a cabinet on the outside of the kitchen that we just happen to find. We chose this house bc it could accommodate 3 generations including 3 grandparents along with two others that have chronic illness. Because of this we could all be affected by the Sargussum & trash that covered both beaches. It is highly toxic to swim in or breathe.
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Top rated by guests
9.4Outstanding
(12 Ratings)
"Fantastic house and location. All the amenities you could ever ask for. The host was very responsive and immediately took care of the issues that arose."
Dennis L.Don't miss out! Price and availability may change
