The Gilded Pineapple

Monthly Rentals Only - Choose 29 Nights for a Full Quote

Address: 327 William Street Location: Key West Type: Private Home
3 Beds 3 Baths Sleeps 6 Pets Allowed
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
THE GILDED PINEAPPLE is a classic Key West home located on one of the most desirable streets in Old Town. This completely renovated, historic home gets its’ name from the elegant, oversized golden door knocker shaped like a pineapple that graces the front door – one of the many subtle touches that adds to the charm. THE GILDED PINEAPPLE features a welcoming front porch with rocking chairs and delicate gingerbread accents. The spacious backyard offers a private pool and is surrounded by lush, tropical foliage. Located just down the street from the historic seaport, you’ll be within walking distance to the best restaurants, shopping, and attractions Key West has to offer. Best of all, a month at THE GILDED PINEAPPLE includes Last Key Realty’s unrivaled Guest Services and Complimentary Concierge, known for providing treasured vacation experiences.


THE GILDED PINEAPPLE is located on William Street, just down a couple blocks from both the historic seaport and World-Famous Duval Street. Situated on one of the best blocks in Old Town, this private home gives you the feeling of being away from it all yet is only a short stroll from everything that Old Town has to offer. Whether you’re looking to spend the day on Duval Street or watch the boats come and go at the seaport, you’ll be there in just a few minutes. You won’t need a car to get around from this location, but if you decide to bring one, there’s an off-street parking spot waiting for you in the driveway. There’s also a designated handicapped parking space right in front of the home on William Street.


The living area and kitchen are in the back of the house. The back French Doors allow natural light to flow in and open to the pool area. The living area features comfortable seating options for the whole group and a large flat screen TV to gather around for the big game or to binge watch your favorite show. The fully equipped kitchen features stainless steel appliances and every cooking tool needed to prepare meals at home. The indoor dining table comfortably seats six, and there’s additional seating at the kitchen bar. A convenient side door connects the driveway to the kitchen, making unloading groceries a breeze. There’s also a full bathroom off the kitchen that connects to the pool area.


Step out the French Doors of the living area and kitchen into your private backyard oasis. The entire backyard is fenced in and landscaped for maximum privacy. The beautiful private pool can be utilized year-round thanks to the convenient heater/chiller that allows you to adjust the pool temperature to your liking. Relax on the sunny pool deck in the chaise lounges or hang in the shade under the umbrella while watching the outdoor TV. Treat your group to a poolside BBQ of today’s fresh catch using the propane Blackstone flat top grill and outdoor dining set with seating for six. Whether you are floating around the pool, preparing a meal on the grill, or toasting before a night out on the town, the pool area is certain to be a primary gathering place for your group.


** Master Bedroom - Located on the Second Floor with a King bed, a flat screen TV, dedicated workspace with color Canon printer, and an en-suite bathroom with two vanities, a walk-in shower, and a garden tub.

** Bedroom #2 – Located on the First Floor with a King bed, a flat screen TV, double closets, and direct access to the Jack-n-Jill bathroom with a shower and tub combo.

** Bedroom #3 – Located on the First Floor with Two Twins OR One King (you decide), a flat screen TV, a closet, and direct access to the Jack-n-Jill bathroom with a shower and tub combo.


** Washer and Dryer
** Central Heat and A/C
** Ceiling Fans
** Flat Screen TVs in Living Room & All Bedrooms
** Fully Equipped Kitchen
** Basic stock of spices
** Starter supply of paper products
** Starter set of cleaning products
** Linens and Towels provided
** Wireless high-speed Internet access & full cable included

In addition, this fully stocked home also includes, but is not limited to the amenities on this list:

** Fully Fenced & Lushly Landscaped Private Yard
** Private Pool with Pool Heater & Chiller
** Propane Blackstone Flat Top Grill
** Outdoor TV
** Off-street Parking in the Driveway

Other notes:

** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.
** Additional interim cleanings available
** This property will accommodate up to 6 adults
** Pets Considered (Small Pets Only)

SwipeDrag for Availability
  • Fire Extinguigher
  • First Aid Kit
  • Smoke Detector
  • Car Not Necessary
  • Bath & Pool Towels Provided
  • Linens & Pillows Provided
  • Off-Street - Driveway
  • Hair Dryer
  • Cooking Spices
  • Refrigerator
  • Keurig & Drip Coffee Makers
  • Dishwasher
  • Dishes & Utensils
  • Toaster
  • Microwave
  • Blender
  • Cable
  • TV in Living Room
  • TVs in Every Bedroom
  • WiFi
  • Books
Indoor Amenities
  • Washer
  • Dryer
  • Air Conditioning
  • Iron & Ironing Board
  • Heating
Outdoor Amenities
  • Pool Heat Available
  • Outdoor TV
  • Propane Grill
  • Beach Essentials
  • Private Pool
  • Near Ocean
  • Botanical Garden
  • Churches
  • Downtown
  • Marina
  • Museums
  • Historic
  • Hospital
  • Festivals
  • Library
  • Restaurants
  • Babysitting
  • ATM/Bank
  • Village
  • Cinemas
  • Shopping
  • Medical Services
  • Playground
Nearby Activities
  • Jet Skiing
  • Pier Fishing
  • Tennis
  • Wind Surfing
  • Health Beauty Spa
  • Live Theater
  • Scenic Drives
  • Fishing
  • Walking
  • Beach Combing
  • Snorkeling
  • Spa
  • Massage Therapist
  • Boating
  • Reef
  • Swimming
  • Para-sailing
  • Scuba or Snorkeling
  • Golf
  • Deep Sea Fishing
  • Water Tubing
  • Basketball Court
  • Cycling
  • Sight Seeing
  • Roller Blading
  • Sailing
Perfect For
  • Eco Tourism
  • Family
  • Romantic
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