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Pineapple Cottage/ 526 Southard St( Rear Cottage)

11 Reviews
Bedrooms 2
Property type house
Minimum Stay 3 - 7 nights

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Minimum Stay
3 - 7 nights


Photos and Description of this 2 bedroom holiday home in Downtown - Pineapple Cottage/ 526 Southard St( Rear Cottage)

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

Property Manager
Kimberly Banning and Jose Mendoza II
Speaks English
Manager indicates their response time is:
Within an hour
Calendar last updated:
24 October, 2016
Call Manager


based on 11 holidaymaker reviews

Pineapple Cottage/ 526 Southard St( Rear Cottage)
average rating of 5.0 based on 11 reviews

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.

  • Review Submitted: Sep 20, 2016
  • Date of Stay: Sep 2016
  • Source: VRBO, from HomeAway
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A hidden oasis a half block from Duval Street

  • 5 of 5

You never know what you're getting until you open the door when you rent vacation properties. When we open the door we were beyond happy and pleasantly surprised to see the oasis we walked into.

Pineapple cottage has everything you need for a great stay in Key West .

The location, about a half block from Duval Street is centrally located to the action but you hear none of the noise from the people.

There are excellent restaurants, shopping and a Walgreens just steps away.

The condo is very comfortable for 4 people and has all the amenities you need for cooking, swimming or relaxing.

We have no problem recommending Pineapple Cottage.

We hope you enjoy it as much as we did.

  • Review Submitted: Aug 17, 2016
  • Date of Stay: Jul 2016
  • Source: HomeAway
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Amazing hideaway!!

  • 5 of 5

This is an amazing find! Literally half a block from Duval, but you'd never know when you're in the private backyard and pool. The house was very clean and well supplied, and the description is completely accurate. If anything it downplays what a great find Pineapple Cottage is! The owners are wonderful, they were very helpful both before my trip, giving advice for planning, as well as helping during the trip itself. I would highly recommend Pineapple Cottage!!

  • Review Submitted: Jul 25, 2016
  • Date of Stay: Jul 2016
  • Source: HomeAway
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I think renting Pineapple Cottage fourteen or fifteen times since 2001 says it all.

  • 5 of 5

Our experience year after year is Pineapple Cottage is everything we want in a vacation rental. Private. Comfortable. Nicely decorated. Well equipped. Quiet. Walking distance to just about all restaurants, movies, plus the Gulf and Atlantic Ocean. Parking. Looking forward to our 2017 visit.

  • Review Submitted: May 3, 2016
  • Date of Stay: Mar 2016
  • Source: HomeAway
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1 0

Great vacation getaway

  • 5 of 5

What a great place to stay for vacation. It was clean, cozy and had everything we needed to use, just like at home. Thank you

  • Review Submitted: Jan 22, 2016
  • Date of Stay: Sep 2015
  • Source: HomeAway
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Awesome Property great location!!!

  • 5 of 5

We were there for the week of New Years . We took friends who had never experienced Key West before. The house, pool and location was just perfect. The gardens at the house are beautiful and the house is laid out well for 4 people and provides privacy for each couple with a masterbed room, bath and living area on each floor. Preferred Properties staff always makes us feel welcomed!

  • Review Submitted: Jan 22, 2016
  • Date of Stay: Dec 2015
  • Source: HomeAway
Owner's Response: Thank you for taking the time to send us a response about your stay at the Pineapple Cottage. We are glad to hear you enjoyed the cottage and that the staff made you feel welcome. We hope you will visit Key West again soon, and contact Preferred Properties if you need a place to stay.
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Prices & Availability


  • Rates shown above do not include taxes and fees

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Accommodation and facilities for this holiday house in Downtown in Lower Florida Keys

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

Partner Offers

Portable wifi hotspot

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