Title: Pineapple Beach by Florida Keys Luxury Rentals - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=10768&destination=Islamorada%2C+Florida%2C+United+States+of+America&selected=72284313&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Pineapple Beach by Florida Keys Luxury Rentals ## Photo gallery for Pineapple Beach by Florida Keys Luxury Rentals ![House, 5 Bedrooms | Property grounds - Pineapple Beach by Florida Keys Luxury Rentals (Islamorada)](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/9cd307d9.jpg?impolicy=resizecrop&rw=598&ra=fit) ![House, 5 Bedrooms | Balcony - Pineapple Beach by Florida Keys Luxury Rentals (Islamorada)](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/c5120887.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House, 5 Bedrooms | Exterior - Pineapple Beach by Florida Keys Luxury Rentals (Islamorada)](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/17e25e00.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House, 5 Bedrooms | Beach/ocean view - Pineapple Beach by Florida Keys Luxury Rentals (Islamorada)](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/de2b1ef7.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House, 5 Bedrooms | Private kitchen - Pineapple Beach by Florida Keys Luxury Rentals (Islamorada)](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/4bb0823d.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Pineapple Beach by Florida Keys Luxury Rentals provides everything you need. Guests can connect to free WiFi in public areas. ### Entire home 5 bedrooms4 bathroomsSleeps 12 ## Popular amenities - Parking included - Free WiFi - Beach view ## 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 by Florida Keys Luxury Rentals This smoke-free vacation home features a private beach, free self parking, and free WiFi in public areas. Other amenities include multilingual staff assistance. The vacation home offers towels provided. Recreational amenities at the vacation home include a private beach. ## Property amenities ### Beach - On a private sandy beach ### Parking and transportation - Free self parking on site ### Bedrooms - 5 bedrooms ### Bathroom - 4 bathrooms - Towels provided ### Pets - No pets allowed ### Suitability/Accessibility - No elevator - Smoking not allowed ### Services and conveniences - Multilingual staff ### 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 not reported (host has not indicated whether there is a smoke detector on the property) ### General - Individual decor - Individual furnishings ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/83000000/82820000/82812900/82812846/1efa6e04.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Island Time Starts Here: Cozy Ground Floor Suite in Islamorada Matecumbe - Pool - Kitchen - Washer - Dryer 8.0 Very good 2 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&selected=82812846&PinnedHotelID=82812846&HadPinnedHotel=true®ionId=-1&adults=2) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33490000/33483000/33482942/72091630.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Private Beachfront Paradise Matecumbe - Ocean view - Pool - Kitchen - Washer 9.6 Exceptional 81 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&selected=33482942&PinnedHotelID=33482942&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/35000000/34560000/34553800/34553718/823dc874.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Deep Water Canalfront Home W / Boat Ramp Matecumbe - Ocean view - Kitchen - Washer - Dryer 9.0 Wonderful 14 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&selected=34553718&PinnedHotelID=34553718&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34009600/34009513/0845d75b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach, plus Den Islamorada - Ocean view - Pool - Kitchen - Washer 10 Exceptional 103 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&selected=34009513&PinnedHotelID=34009513&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34120000/34112400/34112304/27982ff2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful 2/2 Florida keys home rental Matecumbe - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&selected=34112304&PinnedHotelID=34112304&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/50000000/49210000/49208600/49208539/54f25629.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### BEAUTIFUL ISLAMORADA KEYS HOME Matecumbe - Pool - Air conditioning - Microwave [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&selected=49208539&PinnedHotelID=49208539&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/38000000/37790000/37788300/37788289/df549c42.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly! Layton - Ocean view - Kitchen - Washer - Dryer 10 Exceptional 63 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&selected=37788289&PinnedHotelID=37788289&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-04-22&endDate=2026-04-23&selected=72284313&PinnedHotelID=72284313&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=72284313,82812846,33482942,34553718,34009513) ## Policies ### Check-in Check-in start time: 4:00 PM; Check-in end time: 7:00 PM Minimum check-in age: 25 ### Check-out Check-out before 10:00 AM ### Special check-in instructions Guests will receive an email within 7 days before arrival with check-in instructions and an access code If you are planning to arrive after 7:00 PM please contact the property in advance using the information on the booking confirmation Information provided by the property may be translated using automated translation tools ### Access methods Access code ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Smoking Smoking is not permitted ### Property payment types ## Important information ### You need to know 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 This property accepts credit cards; cash is not accepted 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 not indicated whether there is a smoke detector on the property ### We should mention This property does not have elevators ### Property is also known as Pineapple Beach by Florida Keys Luxury Rentals Islamorada ## About the area Located in Islamorada, this vacation home is on a private beach. Florida Keys Dive Center and Mangrove Marina are worth checking out if an activity is on the agenda, while those looking for area attractions can visit John Pennekamp Coral Reef State Park and MoradaWay Arts & Cultural District. [Visit our Islamorada travel guide](https://www.expedia.ca/Islamorada.dx10768) [View more Vacation homes in Islamorada](https://www.expedia.ca/Islamorada-Private-Vacation-Homes.d10768-aaPrivateVacationHomes.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%7C24.97333%2C-80.55153&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=kw57SL65ic21hAySi2hmeICPKlc=) 130 Aregood Lane, Islamorada, FL, 33036 ### What's nearby - ![Founders Park](https://images.trvl-media.com/place/6277602/5d27121a-41d9-4db0-85d1-e5cec763c9fa.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Founders Park 2 min drive \- 2.4 km - ![Theater of the Sea](https://images.trvl-media.com/place/6069249/f2ddaf2d-1bee-4677-b974-9de13893f618.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Theater of the Sea 7 min drive \- 7.6 km - ![Islamorada_BudnMarysDiveCenter_6069243-0004](https://images.trvl-media.com/place/6069243/da13ffdf-ddd2-4c35-bedc-c5b570b047e9.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Bud n' Mary's Dive Center 15 min drive \- 17.2 km - Old Road Gallery 15 min walk \- 1.3 km - Baker's Cay Resort Beach 14 min drive \- 16.6 km ### Getting around - Miami Intl. Airport (MIA) 87 min drive ### Restaurants - McDonald's 6 min drive - Circle K 8 min drive - Hog Heaven 6 min drive - Dillon's Pub & Grill 6 min drive - Old Tavernier 4 min drive ## Frequently asked questions ### Is Pineapple Beach by Florida Keys Luxury Rentals pet-friendly? ### How much is parking? ### What time is check-in at Pineapple Beach by Florida Keys Luxury Rentals? ### What time is check-out at Pineapple Beach by Florida Keys Luxury Rentals? ### Where is Pineapple Beach by Florida Keys Luxury Rentals located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Pineapple Beach by Florida Keys Luxury Rentals Reviews ### Expedia's Latest Trends ### Hotels > - [DiamondHead Beach Resort](https://www.expedia.ca/Fort-Myers-Hotels-DiamondHead-Beach-Resort.h200632.Hotel-Information) > - [South Seas](https://www.expedia.ca/Fort-Myers-Hotels-South-Seas-Island-Resort.h40732.Hotel-Information) > - [Tropic Sun Towers](https://www.expedia.ca/Daytona-Beach-Hotels-Tropic-Sun-Towers-By-Capital-Vacations.h1169627.Hotel-Information) > - [Embassy Suites by Hilton Fort Myers Estero](https://www.expedia.ca/Fort-Myers-Hotels-Embassy-Suites-By-Hilton-Fort-Myers-Estero.h1312669.Hotel-Information) > - [Hammock Beach Golf Resort & Spa](https://www.expedia.ca/Daytona-Beach-Hotels-Hammock-Beach-Golf-Resort-Spa.h994170.Hotel-Information) > - [Bahama House](https://www.expedia.ca/Daytona-Beach-Hotels-Bahama-House.h893658.Hotel-Information) > - [Margaritaville Beach House Key West](https://www.expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) > - [Hyatt Regency Coconut Point Resort & Spa](https://www.expedia.ca/Naples-Hotels-Hyatt-Regency-Coconut-Point-Resort-Spa.h792025.Hotel-Information) > - [Holiday Inn Resort Panama City Beach by IHG](https://www.expedia.ca/Panama-City-Hotels-Holiday-Inn-Resort-Panama-City-Beach.h18867.Hotel-Information) > - [Sarasota Surf and Racquet Club](https://www.expedia.ca/Sarasota-Hotels-Sarasota-Surf-And-Racquet-Club.h9728448.Hotel-Information) > - [White Elephant Palm Beach](https://www.expedia.ca/Palm-Beach-West-Palm-Beach-Hotels-White-Elephant-Palm-Beach.h42412055.Hotel-Information) > - [The Resort on Cocoa Beach](https://www.expedia.ca/Cocoa-Beach-Hotels-The-Resort-On-Cocoa-Beach.h329971.Hotel-Information) > - [Hilton Grand Vacations Club in Sandestin Golf & Beach Resort](https://www.expedia.ca/Miramar-Beach-Hotels-Embarc-Sandestin.h1054729.Hotel-Information) > - [Mission Resort and Club](https://www.expedia.ca/Leesburg-Hotels-Mission-Inn-Resort-Club.h2057662.Hotel-Information) > - [Edgewater Beach & Golf Resort by Resort Collection](https://www.expedia.ca/Panama-City-Hotels-Edgewater-Beach-And-Golf-Resort-By-Resort-Collection.h803238.Hotel-Information) > - [The Resort at Longboat Key Club](https://www.expedia.ca/Sarasota-Hotels-The-Resort-At-Longboat-Key-Club.h27542.Hotel-Information) > - [Pink Shell Beach Resort and Marina](https://www.expedia.ca/Fort-Myers-Hotels-Pink-Shell-Beach-Resort-And-Marina.h15603.Hotel-Information) > - [Cedar Cove Resort and Cottages](https://www.expedia.ca/Sarasota-Hotels-Cedar-Cove-Resort-And-Cottages.h8099611.Hotel-Information) > - [Amrit Ocean Resort and Residences - Singer Island](https://www.expedia.ca/Palm-Beach-West-Palm-Beach-Hotels-Amrit-Ocean-Wellness-Resort.h36247449.Hotel-Information) > - [Windsor Island Luxury | Home in Windsor Island Resort, Private Pool, Arcade](https://www.expedia.ca/Davenport-Hotels-Windsor-Island-Luxury-Home-In-Windsor-Island-Resort.h60809096.Hotel-Information) > - [Holiday Inn Express Hotel & Suites Fort Pierce West by IHG](https://www.expedia.ca/Vero-Beach-Hotels-Holiday-Inn-Express-Hotel-Suites-Fort-Pierce-West.h538557.Hotel-Information) > - [The Ben West Palm, Autograph Collection](https://www.expedia.ca/West-Palm-Beach-Hotels-The-Ben-West-Palm.h38983694.Hotel-Information) > - [Hilton Vacation Club Daytona Beach Regency](https://www.expedia.ca/Daytona-Beach-Hotels-Hilton-Vacation-Club-Daytona-Beach-Regency.h40772.Hotel-Information) > - [The Shores Resort & Spa](https://www.expedia.ca/Daytona-Beach-Hotels-The-Shores-Resort-Spa.h15752.Hotel-Information) > - [Zota Beach Resort](https://www.expedia.ca/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information) > - [Casa Del Mar Longboat Key](https://www.expedia.ca/Sarasota-Hotels-Casa-Del-Mar-Longboat-Key.h15602940.Hotel-Information) > - [Hilton Garden Inn Cocoa Beach Oceanfront](https://www.expedia.ca/Cocoa-Beach-Hotels-DoubleTree-By-Hilton-Cocoa-Beach-Oceanfront.h4398.Hotel-Information) > - [PGA National Resort ](https://www.expedia.ca/Palm-Beach-Gardens-Hotels-PGA-National-Resort-And-Spa.h10355.Hotel-Information) > - [Compass Hotel by Margaritaville Anna Maria Sound](https://www.expedia.ca/Sarasota-Hotels-Compass-Hotel-By-Margaritaville.h41961327.Hotel-Information)