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

Beachfront holiday home with private pool and kitchen

Photo gallery for Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10

Pool
Exterior
Aerial view
Exterior
Exterior

Reviews

9.2 out of 10
Wonderful
5 bedrooms4+ bathroomsSleeps 10

Popular amenities

  • Parking available
  • Pool
  • Dryer
  • Washer
  • Air conditioning

Explore the area

View map
  • Place, Founders Park
  • Place, Islamorada County Park
  • Place, Theater of the Sea

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds and 1 Queen Bed

Bedroom 3

2 Single Bunk Beds

Bedroom 4

2 Double Beds

Bedroom 5

2 Single Beds and 1 Queen Bed

4 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet

Spaces

Deck or patio
Kitchen
Office
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

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)

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Air conditioning

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House Rules

Check in after 5:00 PM
Minimum age to rent: 25
Check out before 9:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

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
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

About the area

Islamorada

Located in Islamorada, this holiday home is on the beach. Hurricane Monument and Indian Key Historic State Park are local landmarks, and some of the area's attractions include John Pennekamp Coral Reef State Park and Jacob's Aquatic Center. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
Map
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?

Checkout 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 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).

About the host

Hosted by Mallory Pinto

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests