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 pristine white sandy beach and crystal-clear waters, your dream is about to come true!

This exquisite estate boasts a gourmet kitchen and a dining area that accommodates 10 guests, offering breathtaking water views. With three levels, there's ample space for you and your guests to spread out. Unwind in the living room, where a 65” TV awaits your movie nights, or engage in a friendly foosball game. Outdoors, indulge in your private beach, complete with a fire pit, boat dock, pool with spa, pool bar, golf green, and abundant outdoor seating to soak in the mesmerizing ocean views.

The main kitchen includes full size refrigerator, wine cooler, ice maker, two dishwashers, microwave, stove, Keurig, dual ovens, mini fridge, toaster oven, coffee maker, blender and 35” TV.

The exterior amenities of this exceptional property are designed for ultimate relaxation and entertainment. The private dock is capable of accommodating boats up to 32 feet with a draft less than 36 inches and a width no greater than 12 feet. Enjoy the heated pool and spa, complemented by a pool bar, seating area, and an invigorating outdoor shower. Unwind by the fire pit, engage in friendly competitions with the foosball table, cornhole, and basketball hoop, or simply relax in the hammocks. A dedicated golf green adds to the recreational offerings. The property boasts a 213-foot private beach with convenient water entry. For aquatic adventures, 2 kayaks and 2 paddleboards are available onsite, with easy launch access at the property's water entry point. With ample parking for multiple vehicles and/or a boat trailer, this property requires a minimum 7-day rental and strictly adheres to a no-pets policy.


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. Islamorada allows 2 adults per bedroom, children over 6 shall be considered adults.

From November - April, there is an additional $150 charge/week for pool heat. We do recommend heating the pool during this time for optimal comfort and enjoyment. You may contact us if you do not want to have the pool heat on, for a $150 discount.

Cancellation Policy: We maintain a strict 60-day cancellation policy. If the cancellation is made at least 60 days before the arrival date you can cancel your reservation and receive a full refund, excluding processing and admin fees. If you cancel within 60 days of the arrival date and we are able to secure another booking for the same time by opening the calendar, you will receive a full refund, minus processing and admin fees. If we are unable to secure another rental for the specified time, the security deposit will be the only amount refunded.

Payment Schedule: Half of the rent and the security deposit are due seven days after booking online, with the full balance required 60 days before check-in. Payment options include credit card or check after signing the contract. A 3.5% fee applies to credit card transactions, which can be waived by opting for payment via check. Please inform us of your preferred payment method after booking. For last-minute bookings, a credit card will be required.

Contract: Upon confirmation of your booking by our office, you will receive an Adobe E-Sign contract for signing. Once signed, the contract will be automatically returned to us. Specify whether you prefer the first payment to be processed with the card on file or another Visa, MasterCard, or check. Payments are only processed after signed contract is received, and all transactions are manually handled.