Title: Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 Reviews, Deals & Photos 2025 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/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 holiday 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) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100780000/100777800/100777736/04394153.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100780000/100777800/100777736/45d3b57b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100780000/100777800/100777736/d3e6ba32.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 - - Parking available - Dryer - Pool - Washer - Kitchen ## 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 transport - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Hob - Ice maker - Kitchen island - Microwave - Oven - Refrigerator - Spices - 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 - Smoke-free property ### 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 - Snorkelling 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 organised 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 - Sea view - Pool - Kitchen - Washer 10 Exceptional 105 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&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 - Sea view - Pool - Kitchen - Washer 9.4 Exceptional 98 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&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) ### Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7 Matecumbe - Sea view - Pool - Kitchen - Washer 10 Exceptional 85 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=32583358&PinnedHotelID=32583358&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/54000000/53040000/53031600/53031525/w1924h1288x0y1-e5e79d12.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks Matecumbe - Sea view - Pool - Kitchen - Washer 10 Exceptional 59 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=53031525&PinnedHotelID=53031525&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33580000/33571500/33571466/feb62235.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### BEACHFRONT POOL HOME Key Largo - Pool - Hot tub - Kitchen - Washer 9.6 Exceptional 106 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=33571466&PinnedHotelID=33571466&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/102000000/101970000/101967900/101967816/c213f630.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful Ocean Front Beach House in Islamorada. 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The provision of housing is linked to their trade, business or profession. Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed On-site parties or group events are strictly prohibited Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has indicated that there is a smoke detector on the property Safety features at this property include a fire extinguisher and a deadlock This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal. ### Property is also known as 1708-257540 ## About the area Located in Islamorada, this holiday home is on the beach. The area's natural beauty can be seen at John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park, while Old Road Gallery and History of Diving Museum are cultural highlights. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with hiking and ecotours. [Visit our Islamorada travel guide](https://www.expedia.co.uk/Islamorada.dx10768) [View more Holiday homes in Islamorada](https://www.expedia.co.uk/Islamorada-Private-Holiday-Homes.d10768-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ![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, FL ### What's nearby - Islamorada County Park - 3 min drive - 1.7 miles - Founders Park - 3 min drive - 1.5 miles - Florida Keys Dive Center - 4 min drive - 2.5 miles - Theater of the Sea - 8 min drive - 5.0 miles - Windley Key Fossil Reef Geological State Park - 8 min drive - 5.0 miles ### Restaurants - ‪McDonald's - ‬6 min drive - ‪Hog Heaven - ‬6 min drive - ‪Dillon's Pub & Grill - ‬6 min drive - ‪Marker 88 - ‬11 min walk - ‪Craig's Restaurant - ‬4 min drive ## Frequently asked questions ### Does Pineapple Beach : 5 BR, 4.5 BA 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 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 in Islamorada, Sleeps 10? > Check-in begins at 5:00 PM. ### What time is check-out at Pineapple Beach : 5 BR, 4.5 BA in Islamorada, Sleeps 10? > Checkout is at 9:00 AM. ### Where is Pineapple Beach : 5 BR, 4.5 BA in Islamorada, Sleeps 10 located? > Nestled on the beach, this Islamorada holiday 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 miles (5 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 Reviews 9.2 ### Wonderful All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.co.uk/lp/b/content-guidelines) ### 8.8 Cleanliness ### 9.6 Location 10 - Excellent 7 8 - Good 2 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 8/10 Good #### Paul M. 9 Mar 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Fantastic family retreat Amazing home for a family to enjoy. ##### Paul M. Stayed 7 nights in Jan 2025 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Kara C. 13 Apr 2025 #### Amazing Property 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! ##### Kara C. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### ryan k. 3 Apr 2024 #### Klein 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! ##### ryan k. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Tess B. 2 Feb 2024 #### Pineapple Beach 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! ##### Tess B. ### 6/10 Okay #### Jessy R. 15 Jun 2025 Liked: Location Disliked: Communication 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. ##### Jessy R. Stayed 7 nights in Jun 2025 ### 8/10 Good #### Ashley T. 21 Jun 2025 ##### Ashley T. Stayed 7 nights in May 2025 ### 10/10 Excellent #### Josh C. 13 Apr 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy ##### Josh C. Stayed 7 nights in Mar 2025 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Gern J. 22 Jul 2024 #### Jaeger/MacKrell family vacation 2024 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. ##### Gern J. ### 10/10 Excellent #### Amanda M. 29 Jun 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing Vacay! 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! ##### Amanda M. 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