THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!
A FUSION OF LUXURY AND HISTORY… This stunning Victorian estate has been meticulously renovated, offering the elegant allure of cosmopolitan tropical style with a nostalgic nod to the charming refinement of the early 19th century. Situated in the Historic Seaport neighborhood of Old Town, the graceful exterior is permeated with respect for its architectural history as your eyes take in the delightful Victorian wooden facade. Once you step inside, however, you are greeted with all the modern amenities and opulence expected in an upscale contemporary residence. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS AND AMENITIES… A serene and elegant ambiance infuses the interior space as you step inside. You are immediately greeted by an entrance hall that features an elegant wooden staircase from the 1930s, which leads to 4 upstairs guest room suites. The great room offers a wide open layout with a large sitting area (Youtube TV live streaming available), infused with an abundance of sunlight flooding the welcoming gathering area. The stylish dining space and adjacent state-of-the-art chef's kitchen invite hours of happy conversation over tropical culinary feasts with loved ones. Just off the kitchen is a modern half-bathroom and a laundry room that offers two sets of washers and dryers. There is a Ring doorbell located on the front door for security purposes.
SLEEPING ARRANGEMENTS… All 4 guest suites reside on the 2nd floor with their own shower bathrooms. Each is uniquely decorated and furnished with high-quality furniture. There are two queen beds and two king beds for guests to enjoy. The living room has a sofa sleeper with a nearby powder room.
OUTDOOR LIVING… Expansive gingerbread porches span the entire front of the house, inviting you to enjoy the lush surrounding views. The backyard evokes a sense of cozy tropical privacy, boasting a beautifully crafted lap swimming pool which comes heated in the cooler months. Dine al fresco after grilling your fresh catch on the luxurious sun deck with soothing cascading waterfall sounds from within the pool.
PARKING... This homes comes with 1 off street parking spot.
PETS... This is NOT a pet friendly home.
MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable)
BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.
CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!
CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund.
Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).
ENDLESS CARIBBEAN CHARM…
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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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Key West
Key West Historic District, a neighbourhood in Key West, is home to this holiday home. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Sails To Rails Museum at Flagler Station and The Kite House are also worth visiting.
Harry S. Truman Little White House - 7 min walk - 0.7 km
Florida Keys Beaches - 8 min walk - 0.7 km
Mallory Square - 10 min walk - 0.9 km
Ernest Hemingway Home and Museum - 14 min walk - 1.2 km
Getting around
Key West, FL (EYW-Key West Intl.) - 9 min drive
Restaurants
Schooner Wharf Bar - 5 min walk
Kermit's Key West Key Lime Shoppe - 4 min walk
Stinkin Crawfish Key West - 6 min walk
Margaritaville - 5 min walk
The Bull & Whistle Bar - 5 min walk
Frequently asked questions
Does THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!?
As of 7 May 2026, prices found for a 1-night stay for 2 adults at THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking! on 1 June 2026 start from AU$448, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking! pet-friendly?
No, pets are not allowed at this property.
How much is parking at THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!?
On-site parking is available at the property.
What time is check-in at THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!?
Check-in begins at 4:00 PM.
What time is check-out at THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!?
Checkout is at 10:00 AM.
Where is THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking! located?
Located in Key West Historic District, this holiday home is within a 5-minute walk of Donkey Milk House and Duval Street. Florida Keys Beaches and Mallory Square are also within 15 minutes.
About the host
Hosted by Wendy Zintsmaster & Team
Languages:
English
Premier Host
They consistently provide great experiences for their guests