Pineapple House on LGI! Bayfront home with pool!

This one-of-a-kind, three-story waterfront home sits directly on the bay and offers the perfect blend of space, privacy, and unforgettable views. With no neighbors directly next door, you’ll enjoy peace, quiet, and plenty of room to relax with family and friends.


This spacious home features 4 bedrooms and 3.5 bathrooms, comfortably accommodating a large family or group. Three bedrooms are located on the main level, while the private primary suite is upstairs. Each bedroom is equipped with a smart TV. The main level includes two full bathrooms, the primary bathroom is upstairs, and a convenient half-bath is located just off the kitchen.


Hardwood floors run throughout the home, and multiple living spaces make it easy for everyone to spread out. The main level offers a cozy living room and kitchenette, while the second level features a second living room, dining area, and a well-stocked full kitchen—perfect for gathering after a day on the water.


One of the home’s standout features is the abundance of outdoor living space. Fully screened porches wrap around both the main level and the second floor, offering breezy, shaded spots to unwind. The third floor provides access to open-air porches on both the bay side and the beach side, where you’ll enjoy stunning sunrise and sunset views with no rooms—just fresh air and scenery.


Step outside to your private dock on the bay, ideal for boating, fishing, or simply soaking in the coastal views. When it’s time to cool off, take a dip in the private heated pool, perfect for year-round enjoyment.


Please note: this home has a lot of stairs and no elevator, so it may not be the best fit for guests with mobility concerns.


If you’re looking for a unique, spacious island retreat with incredible views, privacy, and room to make lasting memories, this home is the perfect getaway. We can’t wait to host you!

The Pineapple House is located on Little Gasparilla Island, which is a bridge-less barrier island. You will need to make an appointment with the water taxi, rent a boat, or bring your own boat. Bringing your own boat? The house has access to a private dock that is just a few steps away from the house. The dock has a 25ft. maximum and only allows 2 boats.

For the water taxi, you’ll park your car at Eldred’s Marina and load your luggage on the water taxi there. The water taxi is $30 for up to 2 people, one way. Each additional person is $15, one way. The water taxi is by appointment only and its hours are 8:30-5:00. You can book appointments outside the normal hours of operation, but the cost is higher and varies based on the time.





Bedrooms:
Bedroom 1 (main floor): Full and twin bed
Bedroom 2 (main floor): Full and twin bed
Bedroom 3 (main floor): 2 twins, trundle bed
Master Bedroom (second floor): King bed


Bathrooms:
Bathroom 1 (main floor): Full bath with clawfoot bathtub
Bathroom 2 (main floor): Full bath with walk-in shower
Master bath (second floor): full bath with walk-in shower
Bathroom 4: (second floor): half bath – near the kitchen

Accommodates 8 guests (10 guests maximum **extra occupant fee $25 per guest/ per night for over 8 guests)


No Smoking.

Amenities
Inside amenities: Air-conditioning, washer and dryer, Wi-fi

Kitchen: Dishwasher, microwave, drip coffeemaker, espresso machine, Keurig, basic kitchen and baking necessities
Living area: smart TV

Outside amenities: Propane Blackstone grill, outdoor shower, beach chairs, beach umbrella, 3 kayaks


Pool with heater

Dock with electric and water.

There are not any grocery stores or restaurants on the island, but there is a grocery delivery service.

Golf cart is not included with rental – but there are 2 golf cart rental companies available on the island.


A rental agreement will be sent after booking and must be reviewed and signed by the primary guest to complete the reservation.


Pet policy: No cats. $100 per pet. Dogs are allowed, but specific breeds may not be allowed. We reserve the right to not allow untrained and aggressive dogs. This is a dog friendly island; therefore, you may encounter other dogs. If your dog is aggressive towards other dogs or people, we do not allow them.
Dogs are allowed, but specific breeds may not be allowed. We reserve the right to not allow untrained and aggressive dogs. This is a dog friendly island; therefore, you may encounter other dogs. If your dog is aggressive towards other dogs or people, we do not allow them.