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Pineapple Beach

Islamorada

From $2150 / night

Summary

Type Signature Villa
Bedrooms 5
Bathrooms 4
Guests 12
King Beds 1
Queen Beds 2
Full Beds 4
Twin Beds 6
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Ever have a dream of sitting at your very own oceanfront private pool, overlooking a beautiful white sandy beach and crystal-clear waters…look no further! Pineapple Beach is nestled on over 3 acres in the heart of Islamorada. This private 5 Bedroom luxury home is what you have been dreaming about, nightly bonfires, competitive putting green, cabana bar, private dock and so much more. Pack your bag and come enjoy a vacation you will never forget! This amazing estate features a gourmet kitchen and dining for 10 with amazing water views. With three levels there is plenty of room for you and all your guest to enjoy. You can relax in the living room and watch a movie on the 65” TV or enjoy a game of foosball. Outdoors you will enjoy your private beach, fire pit, dock for your boat, pool with spa, pool bar, golf green and plenty of outdoor seating to enjoy the breath taking views of the ocean. Key Features of Pineapple Beach: -5 Bedroom / 4.5 Bath: The master bedroom on the main level features a King bed with water view and porch access, ensuite bathroom with shower and soaking tub. The upstairs has two bedrooms, each have a Queen and twin bed. Both bedrooms have ensuite bathrooms, one with a shower and the other with a shower tub combination. There is also an additional side room upstairs with built in twin beds. The lower level has two additional bedrooms. One bedroom has two bunk beds, and the other room has two full beds. The lower-level bedrooms share a bathroom with shower. -The main kitchen includes full size refrigerator, wine cooler, ice maker, two dishwashers, microwave, stove, Keurig, dual ovens, mini fridge, toaster oven, coffee maker, blender and 35” TV. -Washer & Dryer -Dock will accommodate up to a 32’ boat with draft less than 36” and no wider than 12’. -Heated pool and spa. Pool bar and seating and outdoor shower. -Fire Pit -Foosball Table, Corn hole, Basketball Hoop, Two Hammocks, Golf Green -213’ Private Beach with water entry. -2 kayaks & 2 Paddle boards onsite for guest use. Easily launch kayaks at the water access on property. -Enough parking for several vehicles and/or boat trailer. -Minimum 7day rental. -No Pets. ***Reservation Deposits & Payment Due Dates: A security deposit of $2500.00 is required at the time of booking to hold the reservation. 50% of the total, is due 120 days prior to arrival and the remaining balance is due 90 days prior to arrival*** Sargassum seaweed affects the coasts of the Florida Keys, and Islamorada has its share, which ebbs and flows based on winds and tides, collecting on the shoreline at different times of the year. . Sargassum is just another part of Nature’s rich tapestry. In the open ocean, this seaweed serves as a nursery ground and natural haven for sea life, offering food, sanctuary, and breeding grounds for crab, shrimp, whales, sea turtles, migratory birds, and over 120 species of fish. SPRING AND SUMMER MONTHS are greatly affected, as this is not cleared out during this time period.

Amenities

Private Pool
Private Pool
Spa
Spa
Games Room
Games Room
Conservation View
Conservation View
Water View
Water View
WiFi
WiFi
Internet
Internet
High Chair
High Chair
Air Con
Air Con
Free Calls
Free Calls
Wired Internet Access
Wired Internet Access
BBQ
BBQ
Big Screen TV
Big Screen TV
DVD Player
DVD Player
Foosball Table
Foosball Table
Grill
Grill
Hair Dryer
Hair Dryer
TV in Every Bedroom
TV in Every Bedroom
Paved Parking
Paved Parking
Pool Access
Pool Access
Fishing
Fishing
Sofa Bed
Sofa Bed
Beach On Site
Beach On Site
Full Kitchen
Full Kitchen
Laundry In Unit
Laundry In Unit
Laundry On Site
Laundry On Site
Microwave
Microwave
Dishwasher
Dishwasher
Dock
Dock
Ocean Front
Ocean Front
Weekly Homes
Weeklyhomes
oceanside
oceanside
dock
dock
beachview
beach

Video

Availability

Location

Conveniently located in the heart of downtown Islamorada near shops and restaurants.

Rates

Rates are exclusive of Monroe County tax of 12.5%.

Reservation Deposits & Payment Due Dates:

A security deposit of $2500.00 is required at time of booking to hold the reservation.

50% of total, is due 120 days prior to arrival and remaining balance is due 90 days prior to arrival. If booking within 16 weeks of arrival date payment is due in full upon booking.

Reviews

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Rental Rate Notes
$ rates exclusive of tax at 12.50%

If booking within 16 weeks of rental then payment is due in full.

Rates are exclusive of Monroe County tax of 12.5%.

Reservation Deposits & Payment Due Dates:

A security deposit of $2500.00 is required at time of booking to hold the reservation.

50% of total, is due 120 days prior to arrival and remaining balance is due 90 days prior to arrival. If booking within 16 weeks of arrival date payment is due in full upon booking.

 
Date From (Ascending)
Date To 
Daily $ 
[Collapse]2023
 Low Season Aug 01, 2023Dec 16, 20232150.00
 2023 PINEAPPLE BEACHDec 17, 2023Jul 31, 20242500.00
[Collapse]2024
 LOW SEASONAug 01, 2024Dec 14, 20242150.00
 2023 PINEAPPLE BEACHDec 15, 2024Jan 04, 20252500.00
[Collapse]2025
 BASE RATE 2025Jan 05, 2025Jul 31, 20252500.00
 Low SeasonAug 01, 2025Dec 14, 20252150.00
 HolidayDec 15, 2025Jan 03, 20262500.00

 

Guest Reviews

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Reviewer Name: The Peterson and Miller Families

Review Date: Jul 23, 2021
Star Rating:
Thank you for sharing this beautiful home, it was wonderful. We had a family of 8 adults and 3 very young children. All of us could not have been more happy with the pool, the ocean, the sand, the putting green, the tiki bar, the fire pit and all the rest. We actually have a beach house in the panhandle of Florida, but wanted to visit the Keys. Nothing about the trip disappointed us! Plus, we like to think we know a little bit about what ought to come with a really nice home on the beach and this one beat them all. What a place!
Reviewer Name: D. Romer

Review Date: Jul 03, 2021
Star Rating:
We have really enjoyed this house and dealing with you. You’re the BEST. We used all of the amenities and games - this place is self sufficient. Living like the movie stars !!! PLEASE Thank the owners for sharing their MAGNIFICENT PARADISE with my family! Thank you again for working with us and BEST OF WISHES.
Reviewer Name: The Goeddel Family

Review Date: Jun 24, 2021
Star Rating:
We were blessed to celebrate our 50th wedding anniversary with our family at this luxurious home. With 6 adults and 3 children ranging in age from 8 years to 4 months, the accommodations were perfect. We all enjoyed the outdoor bar and pool area, as well as the many "toys" that were available to us, especially the putting green and the chipping game. We thank you for sharing this magnificent home!
Reviewer Name: The Brown Family

Review Date: Dec 19, 2020
Star Rating:
Thanks for an amazing retreat just before the holidays at Pineapple Beach! You can feel the love, warmth and effort you bestowed into this estate. It shines on you at first light (get there before the Peacocks do!) on the south porch. Hospitality draws you in, just like a pinball game adventure, as the windows rise on the bar and the dew lifts off the greens. our attention to the hammock trails shows your commitment to preserving this place for what it offers inland. Then, there's the open waters - to the marine world! Beyond the obvious beach frontage creations, your dedication to small spaces, like the fire pit area, returns us to our ancient roots just earshot from mermaid lagoons! Inside, the interior expands to fit any family. At every turn there's attention to Caribbean memories and oceanic exploration. Your impressions seared into our young family like the strong morning sun. Eight species fresh caught and served. A Blue crab boil as a science lesson . Virtual school alphabet in the sand. We never forget our times here. May future blessings bring you continued happiness and grace as others find your treasure! Thanks for your friendship, courtesy and accommodation! Thank You!
Reviewer Name: The Tinch's , Alvarado's, Gray's, Bridges and Fulk's

Review Date: Oct 30, 2020
Star Rating:
Thank you for sharing your home with us. we came together for a 50th birthday. We had 5 couples from Florida, Ohio, and Arkansas. We made some amazing memories that will last a lifetime. Night fishing off the dock, million dollar putt off on the golf course. Morning coffee on the back dock. Late night swim & spa, and walking the trails on the property. We did our best to treat your home like it was ours and hopefully we will be back in the future.
Reviewer Name: The Limberts, Goldens, Grahams, and Millers

Review Date: Sep 19, 2020
Star Rating:
Thank you so much for sharing your home with us. we had a wonderful time. This house truly has everything from relaxing in the pool, to a friendly putt-putt match while watching the US open to watching the sun come up over a cup of coffee. Fishing was great whether from the pier or at the Islamorada Humps. Thank you so much and we hope to come back.
Reviewer Name: Grammy Rantz

Review Date: Jul 30, 2020
Star Rating:
What a wonderful time we had at your lovely home. Thank you for sharing this piece of heaven with us.
Reviewer Name: The Cohen Family

Review Date: Jul 11, 2020
Star Rating:
Thank you so much for sharing your beautiful home with our family. What an amazing property you have for adults and kids. We will be back.
Reviewer Name: The Witmoyer Family

Review Date: Feb 28, 2020
Star Rating:
Thank you! Thank you! Thank you! For sharing your beautiful beach home. We came from PA, IN, WV and TX. We came together for a family vacation among many life transitions. Our oldest son and wife coming from Indiana expecting their first in June (our 1st grand!) Our second son recently married. Our daughter recently engaged and getting married in August (TX), her fiancé in PA, and school in WV. My husband and I along with our youngest, a junior in high school. This week was a gift. An incredible gift to this momma's heart. Your home offered so much space, each with our own room. The pool, hot tub, tiki bar, putting green, dock, kayaks, paddle boards also offered our crew activities to just plain spend quality time together. We went out every other night and had one couple cook the other nights. The kitchen is so well stocked. I hope and pray we honored you in respecting your home. Again, thank you for sharing. We would love to return some day.
Reviewer Name: The Myers

Review Date: Sep 01, 2019
Star Rating:
Thank you for sharing your beautiful home with us. Our family and friends have memories here that we will cherish forever. Thank you!!!
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