Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 | House in Islamorada

9.2 (10 Reviews) |   5 Bedrooms  4 Bathrooms  10 Guests
Islamorada House | Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10

5 Bedroom House in Islamorada

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)

Pineapple Beach : 5 BR, 45 BA House in Islamorada, Sleeps 10 is located in Islamorada. Pineapple Beach : 5 BR, 45 BA House in Islamorada, Sleeps 10 provides accommodation, featuring Barbecue/Outdoor Cooking, Child Friendly, Laundry, among other amenities. This House features Barbecue/Outdoor Cooking, Child Friendly, Laundry, to make your stay a comfortable one.

Pineapple Beach : 5 BR, 45 BA House in Islamorada, Sleeps 10 has 5 Bedrooms , 4 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Islamorada has interesting places to visit. If you want to learn more about the House in Islamorada, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pool
TV
View
Private Pool
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
Bathrooms
  • 4+ bathrooms
  • Towels provided
  • Hair dryer
  • Shower
Bedroom
  • 5 bedrooms
  • Bed sheets provided
  • Dining table
  • Dining room
  • Living room
Kitchen
  • Kitchen island
  • Toaster
  • Cookware/dishes/utensils
  • Microwave
  • Stovetop
  • Refrigerator
  • Oven
  • Dishwasher
  • Water dispenser
Laundry
  • Near laundromat
  • Washing machine and dryer
  • Laundry facilities
Ocean view
  • On the beach
Parking
  • Onsite parking
Pet Friendly
  • No pets allowed
Accessibility
  • Smoke-free property
Activities
  • Birdwatching nearby
  • Bicycle on site
  • Swimming nearby
  • Kayak on site
  • Water sports equipment
  • Tennis on site
  • Water skiing nearby
  • Fishing nearby
  • Basketball nearby
  • Boat on site
  • Fitness facilities nearby
  • Golfing on site
  • Golf nearby
  • Surfing/body boarding nearby
  • Jet skiing nearby
  • Golf privileges
  • Water tubing nearby
Entertainment
  • Smart TV with cable/satellite service
  • Foosball table
  • Arcade/game room
  • Books
  • Games
General
  • At least 80% lighting from LEDs
  • Local culture & ecosystem education
  • At least 10% of profits reinvested in community & sustainability
  • Humane treatment of captive wild animals
  • Local artist showcase
  • English
  • On the waterfront
  • Near the bay
  • Near the sea
  • Near a hospital
  • Near the ocean
  • Office
  • Desk
Guest Services
  • Children's dinnerware
  • Playground
  • Highchair
  • Chef
  • Phone
  • Limited housekeeping
  • Local meal delivery service
  • Concierge services
  • Change of bedsheets (on request)
  • Change of towels (on request)
  • Iron/ironing board
Internet
  • WiFi available
Outdoors
  • Balcony
  • Fenced yard
  • Barbecue grill
  • Garden
  • Firepit
Security/Safety
  • Deadbolt lock
  • 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 installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
Spa
  • Massages
  • Hot tub
  • Heated pool
  • Private pool

Policies

Check-in
Check-in time starts at 5:00 pm contactless check-in available minimum check-in age: 25
Check-out
Check-out before 9:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted

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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

MaryBeth C.
Aug 30, 2025 07:42:39 AM
Review Score:   10
Summary: 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.
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