Heated Pool Oasis - Walk to Restaurants & Bars

Englewood, Florida
$312 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 2 nights

Min Stay

Summary:

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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.



Other Things to Note:

Pet Fees- $35 Pet Fee - Per Pet/Per Night (No Size Limit)

(Capped @ $250/per pet for up to 30 days!)



The fee will be requested through Airbnb after booking.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total Pets Pet Friendly Welcoming Dogs Only
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Annual Offsets Purchased For At Least 10% Of Carbon Footprint At Least 80% Organic Food Locally Sourced Food Is Prioritized Property Does Not Allow Children Recycling Some Profits Reinvested In Community And Sustainability
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Coin Laundry Washing Machine And Dryer
  • PARKING

    Electric Car Charging Station On Site Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • BATHROOMS

    2 Bathrooms Hair Dryer Shower
  • WORKSPACES

    Office
  • THINGS TO DO

    Bicycle On Site Farming Classes Fitness Facilities Nearby Kayak On Site Scuba Diving Nearby
  • ENTERTAINMENT

    Games Video Games Smart TV
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Pool Toys
  • SERVICES AND CONVENIENCES

    Change Of Bedsheets (on Request) Change Of Towels (on Request) Housekeeping (on Request) Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Abby V.

    Submitted Dec 17, 2025

    Stayed Nov 23, 2025

    We picked this house for our trip because it’s close to my in-laws place. It ended up working out very well being so close to them. When I booked the house I didn’t realize the upstairs was totally seperate from the main living space, but it ended up working out fine. We did have a few critters on the main level, but it is Florida so it didn’t bother us too much. Washer/dryer was nice to have! Pool area was nice. Could use a speaker to play some music. My kids loved playing the games and doing the puzzles in the living room. Overall we had a very nice stay!

  • Barry W.

    Submitted Feb 20, 2025

    Stayed Feb 15, 2025

    We really enjoyed our time here, the property has very comfortable beds, and is well appointed. We spent most of our time by the pool. The last night laying back and soaking the stars was magnificent! It is located in close proximity to some beautiful beaches! Our hosts were considerate and accommodating to our needs. Thank you so much for hosting us! We hope to make it back!

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Total

Includes taxes and fees
$312+
View details