Pineapple Properties

(16 rentals)
Pineapple Properties
66
Pineapple Properties of the Florida Keys is a local boutique property management company. What makes my business unique and successful is that I maintain a small group of properties that I provide a high level of very personal hands-on attention to every guest and property owner. I work closely with the housekeeper and her team to ensure every property is perfectly maintained ...
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Pineapple Properties of the Florida Keys is a local boutique property management company. What makes my business unique and successful is that I maintain a small group of properties that I provide a high level of very personal hands-on attention to every guest and property owner. I work closely with the housekeeper and her team to ensure every property is perfectly maintained and always ready for guests! Guests and owners are able to text me directly any time and I respond immediately! I love helping guests with personal recommendations of all my favorite spots to help make their vacation better than they ever imagined!
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! Plus, Sombrero Beach is just down the street (1.3 miles). ...

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Property Type

Marathon Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two kayaks, two bikes, and a Tiki Hut for the ultimate Keys vacation! With plenty of parking for vehicles and a boat trailer, a well-stocked vacation ...

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Property Type

Marathon House

"This rental home has everything!"

We loved our stay at Dockside Retreat! The house was decorated perfectly for a tropical vacation. We used the pool every day. There were pool noodles, kayaks, cruiser bikes etc. We used all of the fun toys. ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private dock (can accommodate up to a 35' boat on a 32' dock), fish cleaning station, private ...

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Property Type

Marathon Villa

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1 BR | 2 BA | Sleeps 2 | Quick View

1

$275

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history that befits its esteemed place along one of the most elegant streets in Key West. Unit # 6 is a second floor, 1BR/2BA unit that is entered on the left side of the building. The condo ...

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Property Type

Key West Condo

"Perfect place for a warm-weather couple!"

The location is perfect! Close to Duval Street, Mallory Square and many fabulous shops. We rode our bikes every morning to Higgs Beach to play tennis then enjoyed the white sand and cool morning breeze ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This beautiful 4 bedroom, 3 bath home is less than 2 minutes from Sombrero Beach just down the street (oceanfront) and less than 15 minutes to open water! Private pool with outdoor tv on the patio, private dock, 2 bikes, 2 kayaks, bait freezer, gas grill! The private dock can accommodate up to a 30' ...

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Property Type

Marathon House

"Family reunion"

Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Blue Turtle Villa at The Tides of Vaca Cut (Unit #4), is a brand new 5 bedroom 4 bath home with a private pool, boat slip, all the toys for the perfect vacation ~ paddle boards, kayak, giant Jenga, giant connect four, ping pong and more! Perfectly situated on the water with stunning views, sunrise and ...

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Property Type

Marathon House

"Beautiful vacation rental"

The home is absolutely beautiful and in a great location, beautiful views and has all the amenities needed for a great family vacation!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Upscale Modern 4 Bedroom 3 Bath Ocean Front Home, Private Pool, Summer Kitchen! Gorgeous upscale decor with a modern coastal feel offers SPECTACULAR oceanfront views and the advantage of the canal for 50' of dockage! Direct open water access!This property is a Saturday to Saturday booking only. ...

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Property Type

Marathon House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $10!A meticulously updated home with beautiful lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, 2 ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip!Perfectly situated on the water with stunning views, sunrise and sunset colors, and direct quick access to both the Atlantic Ocean and the Gulf of Mexico via Vaca ...

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Property Type

Marathon House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

The Blue Turtle Villa, located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool with a heater and a chiller, and all the amenities you would ...

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Property Type

Key Colony Beach Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional ...

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Property Type

Marathon House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Sunshade Villa, located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool and all the amenities you would want for an amazing vacation in ...

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Property Type

Key Colony Beach Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), private dock (up to 35' boat), fish cleaning station, bait freezer and 4 new bikes! Additionally, ...

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Property Type

Marathon Villa

"Everything you could want in a vaca rental"

Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Blue Shell is a delightful new canal front vacation home with a pool, just a minute to the ocean and open water and lots of fun amenities! It is also about 10 minutes from both Coco Plum Beach and Sombrero Beach.The dock is 50' and there is parking on the side of the house for truck and trailer. ...

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Property Type

Marathon House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Tingler Retreat is a newly renovated tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest ...

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Property Type

Marathon House

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