Pineapple Properties

(12 rentals)
Pineapple Properties
Phone number: +1 (407) 733-2128
3
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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Oasis in the Keys. Oasis in the Keys! 3 BR 2.5 BA Direct Ocean Front!

$436

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Boasting stunning floor-to-ceiling ocean views in every room, this newly remodeled 3BR/2.5BA home promises a delightful oceanfront stay in the Florida Keys. Use the four provided kayaks, two paddle boards for fun-filled explorations, or hop on the bikes to cruise the surrounding area. Enjoy a game of ...

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Property Type

Marathon House

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Dockside Retreat. Canal Front, Tiki Hut, Kayaks, Bikes, Pool, Beach!

$425

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Dockside Retreat! Rent one side or both! This 4 bedroom 3 bath canal front home has a private pool, private dock, fish cleaning station, green light under at 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 ...

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Property Type

Marathon House

"Family Vacation"
Reviewed January 11, 2021

This rental has it all for a large group! The beds are very comfortable, the kitchen is stocked with everything you need, and the pool area with the tiki hut offers hours of enjoyment for kids and adults. ...

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Coastal Key. Flexible Cancellation on Future Bookings! Private Pool - Dock

$371

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Beautifully decorated brand new home, located down the street from oceanfront Sombrero Beach, has a private pool, private dock, fish cleaning station, bait freezer, outdoor TV in covered patio, gas grill, 4 bikes, 2 kayaks, 1 paddle board! With 3 bedrooms, 2 bathrooms, a pull out couch, a pack n play ...

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Property Type

Marathon House

"Best Vacation Ever."
Reviewed November 6, 2020

We decided last minute to cancel our Disney trip & head to the keys. With thousands of options i was overwhelmed to say the least. After weeks of researching reading reviews really digging deep i came across ...

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Reel Life. 4/3 Private Pool, Private Dock, Bikes, Kayaks!

$425

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • 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 patio, private dock, 2 bikes, 2 kayaks, bait freezer, gas grill! Private dock that can accommodate up to a 40' boat. ...

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Property Type

Marathon House

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Sombrero Heaven. Sombrero Heaven - Private Pool and Dock, Canal Front, Beach!

$425

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

"SOMBRERO HEAVEN" ~ Updated Villa with neighborhood Ocean Front beach and Second Story Screened Balcony that Over Looks Private Heated Pool and Canal! Everything you need for the perfect keys vacation ~ private dock, fish cleaning station, bikes, beach towels, beach chairs, beach umbrella, beach ...

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Property Type

Marathon Villa

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Villa Abre el Aqua. Modern Pool Home with STUNNING Open Water Views!

$639

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Please note that construction is taking place on the empty lot next door. Not all views are blocked but some are. We are working on getting updated pictures. Please reach out with questions!Upscale Modern 4 Bedroom 3 Bath Ocean Front Home, Private Pool, Summer Kitchen! Gorgeous upscale decor with ...

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Property Type

Marathon House

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Toes in the Water. Toes in the Water - Private Pool and Dock, Canal Front

$425

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Rent one side or both of this gorgeous, brand new, updated canal front Villa! Each side is a 4 bedroom, 3 bath home (pull out couches) with its own private pool, private dock and delegated parking (covered parking for 2 cars with additional parking for cars and/or boat trailer) and gated back yard with ...

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Property Type

Marathon Villa

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Cockadoodledo Vacation Rental. Featured On Hgtv***multiple Month Discount***updated

$439

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

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 pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...

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Property Type

Key West House

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Chillax. "Chillax" Private Pool and Dock, Canal Front, Beach!

$425

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Rent one side or both of this gorgeous, brand new, updated canal front Villa! Each side is a 4 bedroom, 3 bath home (pull out couches) with its own private pool, private dock and delegated parking (covered parking for 2 cars with additional parking for cars and/or boat trailer) and gated back yard with ...

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Property Type

Marathon Villa

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Tingler Retreat. 100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

$527

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This newly renovated tastefully decorated 3 bedroom 3 bath home (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 use are 2 bikes, 3 kayaks ...

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Property Type

Marathon House

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Marathon Angler' s Retreat. Flexible Cancellation on Future Bookings! Private

$450

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and a 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 45' boat on a 30' dock), fish cleaning station, private pool, hot tub, ...

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Property Type

Marathon Villa

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The Blue Turtle Villa. Direct Ocean & Gulf, Bayfront! Brand New! Private

$683

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

The Blue Turtle Villa on Vaca Cut at The Tides (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, ping pong and more! Perfectly situated on the water with stunning views, sunrise and sunset colors and ...

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Property Type

Marathon House

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