Entire home

Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10

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Photo gallery for Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10

On the beach
Fridge, microwave, oven, stovetop
Property grounds
A heated pool
Exterior

Reviews

9.2 out of 10
Wonderful

Entire home

5 bedrooms5 bathroomsSleeps 10

Popular amenities

  • Beach view
  • Parking available
  • Pool
  • Dryer
  • Washer

Explore the area

Map
Islamorada, Florida
  • Islamorada County Park
    ‪3 min drive‬
  • Founders Park
    ‪3 min drive‬
  • Theater of the Sea
    ‪8 min drive‬

Room options

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About the neighborhood

Islamorada

Within a short walk of Old Road Gallery, this vacation home is within 2 miles (3 km) of Islamorada County Park. The vacation home includes a private pool, a kitchen, and a balcony.

What's nearby

  • Islamorada County Park - 3 min drive - 1.7 miles
  • Founders Park - 3 min drive - 1.5 miles
  • Florida Keys Dive Center - 4 min drive - 2.5 miles
  • Theater of the Sea - 8 min drive - 5.0 miles
  • Windley Key Fossil Reef Geological State Park - 8 min drive - 5.0 miles

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪Hog Heaven - ‬6 min drive
  • ‪Blond Giraffe Key Lime Pie Factory - ‬7 min drive
  • ‪Dillon's Pub & Grill - ‬6 min drive
  • ‪Wahoo's Bar & Grill - ‬8 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10

Pineapple Beach – Private Oceanfront Estate in Islamorada

Pineapple Beach is situated on more than 3 acres in the central area of Islamorada. This exclusive 5-bedroom luxury residence is the embodiment of your dreams, offering nightly bonfires, a challenging putting green, a cabana bar, a private dock, and numerous other amenities. Get ready to pack your bags and experience a vacation that will leave an indelible mark!

If you’ve ever envisioned lounging by your own private oceanfront pool, gazing over a wide stretch of white sandy beach and expansive ocean views, your dream is about to come true. This secluded, gated estate offers an unmatched level of privacy and space rarely found in the Florida Keys.

Inside, the home features a gourmet kitchen and a dining area that accommodates 10 guests, offering breathtaking views of the water. With three levels, there’s ample space for everyone to relax and unwind. Settle into the living room for movie nights on the 65” TV or challenge friends and family to a friendly foosball game.

Outdoors, indulge in your private beach area, complete with a fire pit, boat dock, heated pool with spa, pool bar, golf green, and abundant seating to take in the serene coastal surroundings. While the shoreline is maintained regularly, guests should note that seasonal winds and tides can bring natural sargassum seaweed to the beach. This is a normal and expected part of the coastal environment; although it is cleared periodically, it is not possible or environmentally appropriate to remove it continuously.

The main kitchen includes a full-size refrigerator, wine cooler, ice maker, two dishwashers, microwave, stove, Keurig, dual ovens, mini fridge, toaster oven, coffee maker, blender, and a 35” TV.

Exterior Amenities

Private dock accommodating boats up to 32 feet (max draft: 36 inches, width: 12 feet)
Heated pool and spa
Pool bar and shaded seating area
Outdoor shower
Fire pit
Foosball table, cornhole, basketball hoop
Hammocks
Dedicated golf green
213-foot private beach with convenient water entry
2 kayaks and 2 paddleboards with easy launch access
Ample parking for multiple vehicles and/or boat trailer
Booking Policies

Minimum Stay:
A 7-night minimum stay is required by city regulations, with no exceptions. The city determines the maximum occupancy, and it cannot be exceeded (including adults, children, and infants).

Cancellation Policy:
We maintain a strict 60-day cancellation policy. If the cancellation is made at least 60 days before arrival, you can receive a full refund (excluding processing and admin fees). If you cancel within 60 days and we are able to rebook the same dates, you will receive a full refund minus processing and admin fees. If we are unable to secure another booking, only the deposit will be refunded.

Contract:
Upon confirmation of your booking, you will receive an Adobe E-Sign contract for signature, which will be automatically returned to us once signed.

Payment Options:
The total reservation charges include credit card processing fees by default. We gladly accept checks or EFT payments with no additional fees, and in that case, the processing fees can be removed. Credit card payments are subject to the following fees:
– Visa, MasterCard, Discover: 3.5% processing fee (excluding taxes and deposit)
– American Express: Additional 0.99% fee (excluding taxes and deposit)
The vacation home is air-conditioned and features a kitchen, 4.5 bathrooms, and a balcony. There's space to spread out with 5 bedrooms and a dining area. Other standard amenities include a private pool, a washing machine, and a fenced private yard. Limited housekeeping is available.

Property manager

Mallory Pinto

Languages

English

Similar properties

Property amenities

Beach

  • On the beach

Pool/Spa

  • Heated pool
  • Hot tub
  • Massage
  • Private pool

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster
  • Water dispenser

Dining

  • Chef service
  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Firepit
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Office

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Change of bedsheets (on request)
  • Change of towels on request
  • Concierge services
  • Housekeeping (limited availability)
  • Iron/ironing board
  • Meal delivery service
  • Phone

Location highlights

  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Boat
  • Foosball table
  • Golf
  • Heated pool
  • Kayak
  • Optional golf privileges
  • Tennis
  • Water sports equipment
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 10% of profits reinvested in community and sustainability
  • At least 80% lighting from LEDs
  • Bed sheets changed on request
  • Bicycles
  • Garden
  • Humane treatment of captive wild animals
  • Local artist showcase
  • Local culture and ecosystem education
  • Locally-owned and organized tours and activities
  • Towels (changed on request)
  • Water dispenser

Policies

Check-in

Check-in time starts at 5:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 9:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • This property doesn't allow pets

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 5:00 PM
  • Check-out: 9:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, and a deadbolt lock.

Property is also known as

1708-257540

Frequently asked questions

What can I see near this vacation home?

This vacation home is located in Islamorada within a short 15-minute walk of Old Road Gallery. You'll also find Islamorada County Park and Founders Park within a short drive.

Will I be able to park at this vacation home?

No, this vacation home doesn't offer parking.

Is there a spa available at this vacation home?

Spa services at the vacation home include massages.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is a hot tub.

Is Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 good for couples?

At this beachfront vacation home, there are many amenities for couples, including a private pool and access to a chef in each accommodation with some featuring beach views.

Are there hot tubs at Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10?

Yes, this vacation home has a spa tub.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Does this vacation home have connecting rooms?

No, there aren't connecting rooms at this vacation home.

Are there rooms with balconies that I can book at Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10?

Yes, every accommodation at Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 comes with a balcony with some featuring beach views.

Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 6 out of 9 reviews
Rating 8 - Good. 2 out of 9 reviews
Rating 6 - Okay. 1 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

8.6/10

Cleanliness

Reviews

8/10 Good

Ashley T.

Stayed 7 nights in May 2025

6/10 Okay

Jessy R.

Sadly, we feel like for the cost of the house many updates and repairs should made before renting to guests again. There was lack of communication from the property manager in regards to several items although she did mention she was having service issues. There were lack of common items such as paper towels( she said she brought these by but we did not have access to the garage to retrieve) we were also missing cleaning products and the house is in desperate need of a deep clean especially in the kitchen and the drawers of the kitchen. Once we arrived we had 2 smoke detectors beeping in which we had to go and buy batteries to replace and another smoke alarm starting beeping in the middle of the night. We also had to replace three lamps with lightbulbs, unclog the disposal from the previous guests as it was backing up the dishwasher which began to leak and flood under the sink that we had to pull everything out and clean that as well. We had one towel in each bathroom and had to search all over to finally find them in an amour downstairs. On our last day we found a book for the house that would have told us that but it was stuffed in a cabinet on the outside of the kitchen that we just happen to find. We chose this house bc it could accommodate 3 generations including 3 grandparents along with two others that have chronic illness. Because of this we could all be affected by the Sargussum & trash that covered both beaches. It is highly toxic to swim in or breathe.
Stayed 7 nights in Jun 2025

10/10 Excellent

Josh C., Rhinelander, WI

Liked: Cleanliness
Stayed 7 nights in Mar 2025

8/10 Good

Paul M.

Liked: Cleanliness

Fantastic family retreat

Amazing home for a family to enjoy.
Stayed 7 nights in Jan 2025

10/10 Excellent

Amanda M.

Liked: Cleanliness

Amazing Vacay!

We had a group of recent graduates. Pineapple Beach was perfect for us! House has plenty of room, pool and hot tub are great, golf green was lots of fun, fishing from dock was excellent and the sand was the perfect spot for whiffle ball games and spike ball. We came by boat and tie up was excellent depending on the tide. Morning coffee and nighttime dusk were beautiful. We had tons of peacocks visit every morning that we fed. Everything to play putt putt, basketball, cornhole and paddle board are on sight. Hammocks were great chill out spots.We definitely will visit here again!
Stayed 7 nights in Jun 2024