Entire home
THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!
Vacation home near Duval Street in Key West
Choose dates to view prices
Photo gallery for THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!





Entire home
Popular amenities
- Pool
- Kitchen
- Washer
- Dryer
- Free WiFi
- Air conditioning
Explore the area

Key West, FL
- Duval StreetPlace, Duval Street3 min walk
- Mallory SquarePlace, Mallory Square9 min walk
- Ernest Hemingway Home and MuseumPlace, Ernest Hemingway Home and Museum11 min walk
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)13 min drive
Room options
You may also like
Ad

Blue Flamingo Resort Key West
New Town
- Pool
- Hot tub
- Pet friendly
- Free WiFi
4.1 out of 5, Very good, 1,962 reviews
4.1
Very good
1,962 reviews
The price is CA $428
CA $428
CA $559 total
includes taxes & fees
Mar 10 - Mar 11
Ad

The Key West Hotel
Key West Historic District
- Pool
- Pet friendly
- Free WiFi
- Air conditioning
4.6 out of 5, Wonderful, 533 reviews
4.6
Wonderful
533 reviews
The price is CA $535
CA $535
CA $676 total
includes taxes & fees
Mar 3 - Mar 4
Ad

Ella's Cottages - Key West Historic Inns
Old Town Key West
- Pool
- Breakfast included
- Pet friendly
- Free WiFi
4.7 out of 5, Exceptional, 441 reviews
4.7
Exceptional
441 reviews
The price is CA $613
CA $613
CA $758 total
includes taxes & fees
Mar 2 - Mar 3
Ad

La Concha Key West, Autograph Collection
Key West Historic District
- Pool
- Pet friendly
- Free WiFi
- Restaurant
4.4 out of 5, Excellent, 348 reviews
4.4
Excellent
348 reviews
The price is CA $753
CA $753
CA $893 total
includes taxes & fees
Mar 30 - Mar 31
Ad

Eden House
Key West Historic District
- Pool
- Hot tub
- Free WiFi
- Restaurant
4.5 out of 5, Wonderful, 1,004 reviews
4.5
Wonderful
1,004 reviews
Ad

Hyatt Centric Key West Resort and Spa
Key West Historic District
- Pool
- Spa
- Pet friendly
- Free WiFi
4.5 out of 5, Wonderful, 1,001 reviews
4.5
Wonderful
1,001 reviews
The price is CA $607
CA $607
CA $778 total
includes taxes & fees
Mar 22 - Mar 23
About the area
Key West
Seaside stay .Within a 10-minute walk of this Key West Historic District vacation home, you'll find Duval Street and Florida Keys Beaches. Also, Mallory Square is within half a mile (1 km) and Southernmost Point is within 2 miles (3 km).
What's nearby
- Duval Street - 3 min walk - 0.3 km
- Key West Aquarium - 7 min walk - 0.7 km
- Harry S. Truman Little White House - 7 min walk - 0.7 km
- Mallory Square - 9 min walk - 0.8 km
- Ernest Hemingway Home and Museum - 11 min walk - 1.0 km
Getting around
- Key West Intl. Airport (EYW) - 9 min drive
Restaurants
- Kermit's Key West Key Lime Shoppe - 4 min walk
- Stinkin Crawfish Key West - 6 min walk
- Margaritaville - 5 min walk
- Schooner Wharf Bar - 5 min walk
- Fogarty's and Flying Monkey's - 5 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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…
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…
Similar properties

New Construction Conch Style Home in Oldtown with Pool!
New Construction Conch Style Home in Oldtown with Pool!
Old Town Key West
- Pool
- Air conditioning
- Parking available
- Laundry

Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Key West Historic District
- Pool
- Kitchen
- Washer
- Dryer
4.8 out of 5, Exceptional, 11 reviews
4.8
Exceptional
11 reviews

Pool, Laundry, and grilling area
Pool, Laundry, and grilling area
Old Town Key West
- Free WiFi
- Air conditioning
- Parking available
- Laundry
4.0 out of 5, Very good, 1 review
4.0
Very good
1 review

OSPREY STUDIO @ The Colony-Sleeps up to 4
OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
- Pool
- Kitchen
- Pet friendly
- Free WiFi
4.8 out of 5, Exceptional, 55 reviews
4.8
Exceptional
55 reviews
The price is CA $415
CA $415
CA $1,003 total
includes taxes & fees
Mar 4 - Mar 5

Ibis by AvantStay | Close to Duval Street w/ Shared Pool | Month Long Stays Only
Ibis by AvantStay | Close to Duval Street w/ Shared Pool | Month Long Stays Only
Old Town Key West
- Pool
- Kitchen
- Washer
- Dryer
5.0 out of 5, Exceptional, 1 review
5
Exceptional
1 review

Get your ISLAND STLYE on!
Get your ISLAND STLYE on!
Old Town Key West
- Kitchen
- Washer
- Dryer
- Pet friendly
4.8 out of 5, Exceptional, 84 reviews
4.8
Exceptional
84 reviews

PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
Key West Historic District
- Pool
- Kitchen
- Washer
- Dryer
4.9 out of 5, Exceptional, 33 reviews
4.9
Exceptional
33 reviews
The price is CA $2,182
CA $2,182
CA $3,966 total
includes taxes & fees
Mar 2 - Mar 3

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
Key West Historic District
- Pool
- Kitchen
- Washer
- Dryer
4.9 out of 5, Exceptional, 205 reviews
4.9
Exceptional
205 reviews

UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
Old Town Key West
- Kitchen
- Washer
- Dryer
- Pet friendly
5.0 out of 5, Exceptional, 2 reviews
5
Exceptional
2 reviews

Casa Rosa: 4BR/4BA house, pool, near Duval
Casa Rosa: 4BR/4BA house, pool, near Duval
Key West Historic District
- Pool
- Hot tub
- Kitchen
- Washer
4.9 out of 5, Exceptional, 84 reviews
4.9
Exceptional
84 reviews
Property amenities
Pool/Spa
- Heated pool
- Private pool
Internet
- Available in the house: Free WiFi
Parking and transportation
- Parking on site
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Kitchen island
- Microwave
- Oven
- Refrigerator
- Toaster
Dining
- Dining table
Bedrooms
- 4 bedrooms
- Bedsheets provided
Bathroom
- 4.5 bathrooms
- Hair dryer
- Shower
- Towels provided
Living spaces
- Dining table
- Living room
Entertainment
- TV
Outdoor areas
- Balcony
- Barbecue grill
- Fenced yard
Laundry
- Washing machine
Comfort
- Air conditioning
Pets
- No pets allowed
Suitability/Accessibility
- Smoking not allowed
Services and conveniences
- Concierge services
- Iron/ironing board
Location highlights
- In the city center
- Near a hospital
- Near the marina
- Near the sea
Things to do
- Heated pool
- Tennis
- Basketball nearby
- Birdwatching nearby
- Cycling nearby
- Ecotours nearby
- Fishing nearby
- Golfing nearby
- Jet skiing nearby
- Sailing nearby
- Scuba diving nearby
- Snorkeling nearby
- Swimming nearby
Safety features
- Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
- Smoke detector (host has indicated there is a smoke detector on the property)
- Fire extinguisher
- Deadbolt lock
General
- Unit size: 2,448 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
- No pets allowed
Children and extra beds
- Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.
Property is also known as
2450-277074