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Pineapple Cottage/526 Southard St

Bedrooms 2
Property type house
Minimum Stay 3 - 7 nights


About the property

2 Bedrooms, 2 Baths, Sleeps 4

Pineapple Cottage is a two bedroom, two bathroom home with a private pool in Old Town Key West. There is total privacy and charm throughout this island home and the proximity to all things Key West is unbeatable (one block from Duval Street).

Behind an enclosed, white wooden gate there is tropical paradise called Pineapple Cottage. The entrance leads you right to the backyard on the deck with view of the sparkling pool, charcoal grill, multiple seating/lounging locations and the lush tropical landscaping ensuring privacy.

To the right is the two story home with multiple doors leading to the luxurious outside. Upon entry through French doors, the living area and kitchen space are open concept and allow for entertainment. There is a fully equipped entertainment system with complete manual for the cable TV, sounds system, CD player, and DVD player. There are also board games in the living room to lounge with your family. The full kitchen has a breakfast bar and bar chairs giving perfect division from the couch and comfortable viewing chairs of the living room.

On the first level, there is an up to date bathroom and a bedroom hidden off to the right of the kitchen. This bedroom has a queen size bed, nightstands, dresser drawers and French doors leading directly outside. Leave the curtains and blinds closed to sleep in or open, letting the tropical sun wake you for an adventurous day.

The second floor of the home also has a large living space with a cable TV, large comfortable sofa and chairs. The master bedroom on this level has a king size bed and an ensuite, full bathroom. This bathroom also the up to date washer and dryer for the convenience of our guests.

The backyard is a one stop shop; from the sparkling heated pool to the grill and dining areas, you can prepare your meals at home if desired while entertaining. Pineapple Cottage is a top of the line in every way for your total comfort and enjoyment. Old Town district, walk to Duval Street, close to shopping, beaches and restaurants.

** Pool heat optional. $175.00 weekly.


Off Street Parking

Central A/C

Gated Entry

Security System

Wireless DSL

Private Sunny Pool

Fully Equipped Kitchen


Large Deck

Charcoal grill

Cable TV



Pool Heat Optional! Pool heat $175.00 minimum charge weekly

More Details

Angela Hart and Jose Mendoza II
Speaks: english
Manager indicates their response time is:
Within an hour
Calendar last updated:
December 16, 2017

Why Angela Hart and Jose Mendoza II chose Old Town

Pineapple Cottage is secluded and very private. Tucked behind a small boutique store you would not know there is a cottage with a private pool and outdoor dining.


Azur Restaurant
"A local favorite offering breakfast, lunch, and dinner! We highly recommend the Key Lime Fre..."
Lazy Dog Kayak
"Best place to rent kayaks or paddleboards! "

Check out some of our local art museums and off the beaten path restaurants. Ft. Zachary Taylor State Park and Beach is a great place to spend the afternoon. Stop by Sandy's on White St for the best Cuban Sandwich and take a bike ride thru some of our Key West streets.


Old Town House Accommodation and Amenities

Property Type:
  • house
  • Air Conditioning
  • Clothes Dryer
  • Washing Machine
  • Dishwasher
  • Microwave
  • 2 Bathrooms
  • 2 Bedrooms, Sleeps 4
  • Stereo
  • Television
  • Deck / Patio
  • Outdoor Grill
Pool / Spa:
  • Heated Pool
  • Private Pool
Sports & Adventure Activities:
  • golf


Wonderful! 4.9/5 -
(16 traveler reviews)

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Pineapple Cottage/526 Southard St
average rating of 4.9375 based on 16 reviews

Good Place to Stay

  • 4 of 5

Great location with easy walk to Duval St. The pool is an adequate size. The furnishings and beds could use an update but otherwise an ideal place to stay.

  • Submitted: Nov 14, 2017
  • Stayed: November 2017
  • Source: HomeAway
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Very comfortable.

  • 5 of 5

Great location. Lots of comfortable space and loved the patio, garden, pool area. A fabulous place to stay.

  • Submitted: Aug 31, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Pineapple Cottage is the perfect place for privacy but still close to Key West/Duval Street action..

  • 5 of 5

This property has the privacy and convenience that you want. Tall windowless buildings on either side of the property shelter you from noisy/prying neighbors. Double doors open from the family room and the down stairs bedroom onto the expansive deck. There is an upstairs master bedroom with on-suite bath, shower and laundry. The kitchen/family room is well equipped with whatever cooking/eating items you will need. You'll enjoy breakfast under the umbrella on the deck as well as nighttime activities. There is a private back yard entry from your dedicated parking spot as well as room to store your rental bicycles. While a bit pricey, I doubt if you'll find a better place to stay on the island that is so convenient to everything.

  • Submitted: Mar 9, 2017
  • Stayed: February 2017
  • Source: HomeAway
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Loved Pineapple Cottage!

  • 5 of 5

We absolutely loved our stay at Pineapple Cottage. Fantastic location, had everything we needed, the pool was wonderful. Loved that there were a couple of pool floats for sunning, as well as plenty of chaise lounge chairs. We are coming back. Kimberly and Jose were wonderful and helpful with any questions we had. Everything in the cottage was perfect for us; beds were comfortable too!

  • Submitted: Mar 7, 2017
  • Stayed: February 2017
  • Source: HomeAway
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Beaufort, NC

Hidden jem!

  • 5 of 5

Surprisingly intimate property a half a block off of Duval. Private pool was fantastic. Well appointed with off-street parking in private lot. Kimberly and Jose were fantastic throughout the reservation, check-in, duration of stay, check-out and follow up! (We inadvertently left some belongings which they took immediate care of. Highly recommend the Pineapple Cottage and Preferred Properties.

  • Submitted: Oct 29, 2016
  • Stayed: October 2016
  • Source: VRBO, from HomeAway
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Wonderful and clean cottage home

  • 5 of 5

We were impressed from the moment we stepped inside. Cute and clean accommodations. The place was available early. Management was easy to reach. We loved the location to Duval and spent many hours each day in the pool and on the patio. We would definately come back here.

  • Submitted: Sep 20, 2016
  • Stayed: September 2016
  • Source: VRBO, from HomeAway
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  • Rates shown above do not include taxes and fees

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