Islamorada Rentals USA Florida Islamorada

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

9.2 (10 Reviews) |   5 Bedrooms  4 Bathrooms  10 Guests
Islamorada House | Pineapple Beach : 5 BR, 4.5 BA in Islamorada, Sleeps 10

5 Bedroom House in Islamorada

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 small 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 own small 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)

Pineapple Beach : 5 BR, 45 BA in Islamorada, Sleeps 10 is located in Islamorada. Pineapple Beach : 5 BR, 45 BA in Islamorada, Sleeps 10 provides accommodation, featuring Pool, Private Pool, Balcony/Terrace, among other amenities. This House features Pool, Private Pool, Balcony/Terrace, to make your stay a comfortable one.

Pineapple Beach : 5 BR, 45 BA in Islamorada, Sleeps 10 has 5 Bedrooms , 4 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Islamorada has interesting places to visit. If you want to learn more about the House in Islamorada, such as places to visit and things to do nearby, you can check below to learn more.

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Islamorada, 33036, USA

Amenities

Air Conditioner
Parking
Pool
TV
View
Private Pool
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
Bathrooms
  • 4+ bathrooms
  • Towels provided
  • Shower
  • Hair dryer
Bedroom
  • 5 bedrooms
  • Bed sheets provided
  • Dining table
  • Living room
  • Dining room
Kitchen
  • Kitchen island
  • Stovetop
  • Ice maker
  • Refrigerator
  • Microwave
  • Spices
  • Oven
  • Toaster
  • Dishwasher
Laundry
  • Laundry facilities
  • Washing machine and dryer
  • Near laundromat
Ocean view
  • On the beach
Parking
  • Onsite parking
Pet Friendly
  • No pets allowed
Accessibility
  • Smoke-free property
Activities
  • Golf privileges
  • Jet skiing nearby
  • Kayak on site
  • Cycling nearby
  • Boat on site
  • Bicycle on site
  • Golf nearby
  • Swimming nearby
  • Fitness facilities nearby
  • Golfing on site
  • Hiking nearby
  • Water sports equipment
  • Birdwatching nearby
  • Basketball nearby
  • Fishing nearby
  • Tennis on site
  • Surfing/body boarding nearby
Entertainment
  • Foosball table
  • Arcade/game room
  • Games
  • Books
  • Smart TV with cable/satellite service
General
  • Local culture & ecosystem education
  • Humane treatment of captive wild animals
  • At least 10% of profits reinvested in community & sustainability
  • At least 80% lighting from LEDs
  • Local artist showcase
  • English
  • Near the bay
  • Near the ocean
  • Near the sea
  • Near a hospital
  • On the waterfront
  • Office
  • Desk
Guest Services
  • Highchair
  • Children's dinnerware
  • Playground
  • Change of bedsheets (on request)
  • Iron/ironing board
  • Chef
  • Change of towels (on request)
  • Phone
  • Local meal delivery service
  • Concierge services
  • Limited housekeeping
Internet
  • WiFi available
Outdoors
  • Fenced yard
  • Balcony
  • Barbecue grill
  • Garden
  • Firepit
Security/Safety
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock
  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Spa
  • Massages
  • Heated pool
  • Private pool
  • Hot tub

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
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted
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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Jessy R.
Jun 16, 2025 12:04:04 AM
Review Score:   6
Summary: 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.
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FAQ's

Is this Islamorada house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Islamorada house have a swimming pool?

Yes, this Islamorada house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Islamorada house?

Best-rates for the Islamorada house starts from $2,266 per night with includes Hot Tub, Internet, Air Conditioner, TV, View, Oceanfront, Bedding/Linens, Kitchen, Laundry, Ocean View, Barbecue/Outdoor Cooking, Parking, Pool, Private Pool, Balcony/Terrace, Sports/Activities, Wellness Facilities, Guest Services, Entertainment, Security/Safety, Child Friendly With all other amenities included. Treehouse Rentals offers a wide range of treehouses, forest homes, cabins, and off-grid retreats, ensuring each traveler discovers their ideal nature getaway—be it a family adventure, a peaceful retreat, or a pet-friendly retreat with the whole group.

Is Islamorada house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Islamorada house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Islamorada house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Islamorada house?

Based on the information reported by the owner or manager, the Islamorada house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Islamorada house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Islamorada house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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