Pineapple Properties

(13 rentals)
Pineapple Properties
84 reviews
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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Marathon House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
2 reviews

$425

avg/night

$425
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

$595

avg/night

$595
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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 paddle boards, a kayak, four bikes, and a Tiki Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you ...

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Property Type

Marathon House

Featured review

"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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Marathon Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

$606

avg/night

$606
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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 Colony Beach Villa
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
10 reviews

$663

avg/night

$663
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Blue Manatee (formerly 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 can imagine ...

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Property Type

Key Colony Beach Villa

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

$540

avg/night

$540
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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 (1/2 the dock), 2 bikes, 2 kayaks, bait freezer, gas grill! The private dock can accommodate ...

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Property Type

Marathon House

Featured review

"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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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
7 reviews

$826

avg/night

$826
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

Featured review

"Grateful"

I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would ...

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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
10 reviews

$818

avg/night

$818
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

Featured review

"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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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
6 reviews

$856

avg/night

$856
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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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Marathon Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
2 reviews

$599

avg/night

$599
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

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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Key Colony Beach Villa
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
8 reviews

$662

avg/night

$662
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Marathon House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
5 reviews

$726

avg/night

$726
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Key West Condo
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms
2 reviews

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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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Marathon Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
6 reviews

$501

avg/night

$501
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

Featured review

"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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