Heated Pool Oasis - Walk to Restaurants & Bars

Welcome to Pineapple in Paradise a tropical getaway where old Florida charm meets modern luxury. This newly remodeled home features two private living spaces, a sparkling pool, and a fenced backyard with a bar. Perfect for families, couples, or friends to relax, unwind, and make unforgettable memories under the palms.

Send us a message to book your vacation.

The Space:
From the moment you arrive at Pineapple in Paradise, you feel like you’ve discovered your own slice of old Florida charm wrapped in modern comfort. You’ll drop your bags, kick off your shoes, and wander out back to the sound of palm leaves and the sparkle of your private pool. The bar is stocked, the grill is ready, and the pergola calls you to unwind with a drink in hand as the sun melts into the horizon. (We can take care of stocking your fridge, just ask!)

You’ll have room for everyone here, two fully equipped living spaces make it perfect for families or friends traveling together. Downstairs, you’ll find a cozy king and queen bedroom, a full kitchen, and a game-ready living room with a 75” Smart TV and PlayStation 5.

Upstairs, another queen bedroom and lounge space await, giving everyone a place to spread out and relax.

Sleep comes easy on brand-new mattresses wrapped in soft linens, and mornings begin with coffee brewed in your choice of pot or Keurig before heading out to explore.

Dearborn Street’s local cafés are just half a mile away, and Englewood and Manasota Key beaches are only minutes from your door — complete with a Boca Grande bridge pass included.

Spend your days paddle boarding, biking, or lounging poolside with the kids and pups, the home is both family- and pet-friendly, complete with a Pack ’n Play, high chair, and beach toys. When you’re ready to wind down, stream your favorite shows, play a few games, or gather outside under the pergola lights for one last toast to paradise.

At Pineapple in Paradise, every detail is designed for connection, comfort, and that unforgettable Florida feeling , where life slows down, laughter lingers, and every moment feels like vacation.

Guest Access:

Guests have full access to the entire property including downstairs of the home, the private pool and all outdoor/backyard amenities and upstairs apartment.

Boat/Trailer parking is available on-site for your convenience.