Pineapple Beach

About

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 wide stretch of white sandy 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 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, you will receive an Adobe E-Sign contract for signature, which will be automatically returned to us once signed.

Payment Options:
The total reservation charges include credit card processing fees by default. We gladly accept checks or EFT payments with no additional fees, and in that case, the processing fees can be removed. Credit card payments are subject to the following fees:
– Visa, MasterCard, Discover: 3.5% processing fee (excluding taxes and deposit)
– American Express: Additional 0.99% fee (excluding taxes and deposit)