Pineapple Beach

Islamorada, Florida
$2328 avg/night Minimum Stay 7 Nights
Bed 5

Bed

Bath 4

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 7 nights

Min Stay

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, 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)



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

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    On The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Humane Treatment Of Captive Wild Animals Local Artist Showcase Local Culture & Ecosystem Education Some Profits Reinvested In Community And Sustainability Uses Some LED Lighting
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Electric Kettle Microwave Oven Refrigerator Stovetop Water Dispenser
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Firepit Garden
  • POOL/SPA

    Hot Tub Private Pool
  • BATHROOMS

    4.5 Bathrooms Hair Dryer Shampoo Shower Towels Provided
  • WORKSPACES

    Office
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Fitness Facilities Nearby Golf Privileges Kayak On Site
  • ENTERTAINMENT

    Smart TV
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair
  • LOCATION HIGHLIGHTS

    Near The Ocean On The Waterfront
  • SERVICES AND CONVENIENCES

    Change Of Bedsheets (on Request) Change Of Towels (on Request) Iron/ironing Board Limited Housekeeping
  • SUITABILITY/ACCESSIBILITY

    Elevator Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 09:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • MaryBeth C.

    Submitted Aug 30, 2025

    Stayed Aug 9, 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.

  • Jessy R.

    Submitted Jun 15, 2025

    Stayed Jun 7, 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.

  • Kara C.

    Submitted Apr 13, 2025

    Stayed Apr 5, 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!

  • Paul M.

    Submitted Mar 9, 2025

    Stayed Jan 11, 2025

    Amazing home for a family to enjoy.

  • Gern J.

    Submitted Jul 22, 2024

    Stayed Dec 31, 1969

    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: This is the second time we have rented Pineapple Beach. It’s so amazing each time we have visited. Our families have been vacationing together for some time in many different homes. Pineapple Beach is the one. It’s perfect in every way.

  • Amanda M.

    Submitted Jun 29, 2024

    Stayed Jun 22, 2024

    We had a group of recent graduates. Pineapple Beach was perfect for us! House has plenty of room, pool and hot tub are great, golf green was lots of fun, fishing from dock was excellent and the sand was the perfect spot for whiffle ball games and spike ball. We came by boat and tie up was excellent depending on the tide. Morning coffee and nighttime dusk were beautiful. We had tons of peacocks visit every morning that we fed. Everything to play putt putt, basketball, cornhole and paddle board are on sight. Hammocks were great chill out spots.We definitely will visit here again!

  • ryan k.

    Submitted Apr 3, 2024

    Stayed Dec 31, 1969

    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: It was great!

  • Tess B.

    Submitted Feb 2, 2024

    Stayed Dec 31, 1969

    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: Our family had a wonderful stay at this beautiful property and home! Lots of space and activities for all ages. The mini golf was a hit with our teenagers and everyone enjoyed our morning visits from a group of peacocks. Smooth check in / check out process and Keys Ocean Vacation Rentals were quick to answer any questions that we had. Will definitely recommend to others!

You might like these similar properties

Your dates are Available!

Total

Includes taxes and fees
$2,328+
View details