Title: Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 Beachfront vacation home with private pool and kitchen ![On the beach](https://images.trvl-media.com/lodging/101000000/100780000/100777800/100777736/d5597091.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100780000/100777800/100777736/d3e6ba32.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100780000/100777800/100777736/04394153.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100780000/100777800/100777736/45d3b57b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![A heated pool](https://images.trvl-media.com/lodging/101000000/100780000/100777800/100777736/8263d7ef.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Nestled on 3 acres in the heart of Islamorada, Pineapple Beach is a luxury haven offering unparalleled oceanfront living. With a private dock, putting green and cabana bar, unwind by your own pool or indulge in sunset bonfires on the beach. 9.2 Wonderful ### Entire home 5 bedrooms5 bathroomsSleeps 10 ## Popular amenities - Beach view - - Parking available - Dryer - Pool - Washer ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 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) ## Property amenities ### Beach - On the beach ### Pool/Spa - Heated pool - Hot tub - Massage - Private pool ### Internet - Available in the house: WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Ice maker - Kitchen island - Microwave - Oven - Refrigerator - Spices - Stovetop - Toaster - Water dispenser ### Dining - Chef service - Dining table ### Bedrooms - 5 bedrooms - Bedsheets provided ### Bathroom - 4.5 bathrooms - Hair dryer - Shower - Towels provided ### Living spaces - Dining table - Living room - Separate dining area ### Entertainment - Books - Games - Smart TV with cable/satellite channels ### Outdoor areas - Balcony - Barbecue grill - Fenced yard - Firepit - Garden ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Office ### Comfort - Air conditioning ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Change of bedsheets (on request) - Change of towels on request - Concierge services - Housekeeping (limited availability) - Iron/ironing board - Meal delivery service - Phone ### Location highlights - Near a hospital - Near the bay - Near the marina - Near the ocean - On the waterfront ### Things to do - Arcade/game room - Bicycles - Boat - Foosball table - Golf - Heated pool - Kayak - Optional golf privileges - Tennis - Water sports equipment - Basketball nearby - Birdwatching nearby - Cycling nearby - Ecotours nearby - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Jet skiing nearby - Sailing nearby - Scuba diving nearby - Snorkeling nearby - Surfing/bodyboarding nearby - Swimming nearby - Water skiing nearby - Water tubing nearby - Windsurfing nearby ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector (host has indicated there is a smoke detector on the property) - Fire extinguisher - Deadbolt lock ### General - At least 10% of profits reinvested in community and sustainability - At least 80% lighting from LEDs - Bed sheets changed on request - Bicycles - Garden - Humane treatment of captive wild animals - Local artist showcase - Local culture and ecosystem education - Locally-owned and organized tours and activities - Towels (changed on request) - Water dispenser ## Similar properties ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/36000000/35270000/35265400/35265387/56c8be3b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views Matecumbe - Ocean view - Pool - Kitchen - Washer 10 Exceptional 105 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-18&endDate=2025-11-19&selected=35265387&PinnedHotelID=35265387&HadPinnedHotel=true®ionId=-1&adults=2) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/2b862fb7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly Islamorada - Ocean view - Pool - Kitchen - Washer 9.4 Exceptional 99 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-18&endDate=2025-11-19&selected=34015770&PinnedHotelID=34015770&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32590000/32583400/32583358/38e83c14.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Only 3 weeks left in 2025 for a pre-Christmas getaway! 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as 1708-257540 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.97332%2C-80.55151&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=I1JY4kSrowOXPSgO0Kze_YrWIWs=) Islamorada, Florida #### What's nearby - Founders Park - 3 min drive - 2.3 km - Islamorada County Park - 3 min drive - 2.7 km - Florida Keys Dive Center - 5 min drive - 4.1 km - Theater of the Sea - 9 min drive - 7.6 km - Windley Key Fossil Reef Geological State Park - 9 min drive - 7.6 km #### Restaurants - ‪McDonald's - ‬6 min drive - ‪Hog Heaven - ‬6 min drive - ‪Dillon's Pub & Grill - ‬6 min drive - ‪Marathon Bagel Co - ‬4 min drive - ‪Craig's Restaurant - ‬4 min drive ## Frequently asked questions ### Does Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 have a pool? > Yes, this property has a pool. Pool types include heated pools. ### Is Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10? > Check-in begins at 5:00 PM. ### What time is check-out at Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10? > Check-out is at 9:00 AM. ### Where is Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 located? > Nestled on the beach, this Islamorada vacation home is within 2 mi (3 km) of Old Road Gallery, Islamorada County Park, and Rain Barrel Village. Founders Park and Florida Keys Dive Center are also within 3 mi (5 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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