Book Direct & Save - No Service Fees
Pineapple Properties

Pineapple Properties

Member since 2019
13 rentals
115 reviews
  • Filters
  • Price
  • Sleeps
  • Rooms
  • Sort
Marathon House
Sleeps 8, 3 bedrooms, 2.5 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!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 ...

View all property information

$340
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!Tingler Retreat is a 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 ...

View all property information

$511
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
7 reviews

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 ...

View all property information

$670
avg per night
Marathon Villa
Sleeps 10, 4 bedrooms, 3 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!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 ...

View all property information

$455
avg per night
Key Colony Beach Villa
Sleeps 10, 4 bedrooms, 4 bathrooms
13 reviews

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 ...

View all property information

$579
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
13 reviews

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 ...

View all property information

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!

See all reviews

$686
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

JUNE 8-15 @ , PLUS WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!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, ...

View all property information

Featured review

"Fantastic Experience"

We had a fabulous stay in your property. We really appreciated all of your amenities. We love to cook some of our meals in and you had a great selection of pots and pans and dinnerware. We also like ...

See all reviews

$448
avg per night
Key West Condo
Sleeps 4, 1 bedroom, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private 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 ...

View all property information

$198
avg per night
Marathon Villa
Sleeps 10, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

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

About this property

WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!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 ...

View all property information

Featured review

"Wonderful home with a great location"

Meredith and Pineapple Properties were very accommodating, and answered all of our questions. The home, the pool, and the hot tub are all in great working shape, well-maintained, and clean. The property ...

See all reviews

$541
avg per night
Marathon Villa
Sleeps 10, 4 bedrooms, 3 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!"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), ...

View all property information

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!

See all reviews

$455
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
12 reviews

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 ...

View all property information

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 ...

See all reviews

$668
avg per night
Key Colony Beach Townhome
Sleeps 10, 4 bedrooms, 4 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!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 ...

View all property information

$580
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

JUNE 7-14 @ ! PLUS WE ARE OFFERING A 5% DISCOUNT FOR REMAINING WEEKS THROUGH THE END OF AUGUST & SOME FALL DATES!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 ...

View all property information

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.

See all reviews

$362
avg per night
Full map
Map