Entire home

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

Family-friendly fun on the beach, with hot tub

Outdoor dining - Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 (Islamorada)

Interior - Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 (Islamorada)

Nestled on 3 acres in the heart of Islamorada, Pineapple Beach is a luxury haven offering unparalleled oceanfront living. With a private dock, putting green and cabana bar, unwind by your own pool or indulge in sunset bonfires on the beach.

Wonderful

Entire home

5 bedrooms5 bathroomsSleeps 10

Popular amenities

Ocean view
Pool
Kitchen
Washing machine
Dryer

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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

Family-friendly fun on the beach, with hot tub

Guests at this beach holiday home will appreciate convenient on-site amenities such as a playground and barbecue grills. The holiday home has 5 bedrooms and offers a fenced private garden and a balcony. Guests can enjoy a private pool, and other amenities include a kitchen with a fridge and an oven. Limited housekeeping is available.

Air-conditioned accommodation at this holiday home offers private pools and coffee/tea makers. Rooms open to balconies. This accommodation is furnished with dining tables and kitchen islands. Kitchens offer fridges, stovetops, microwaves and separate dining areas. Bathrooms include a shower and hairdryers.

Smart televisions are featured in guestrooms. Business-friendly amenities include offices, desks and telephones. Change of towels and change of bedsheets can be requested. Housekeeping is provided on a limited basis.

Recreational amenities at the holiday home include Access to hot tub.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Property amenities

Beach

On the beach

Pool/Spa

Heated pool
Hot tub
Massage
Private pool

Internet

Available in the house: WiFi

Parking and transport

Parking on site

Kitchen

Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Ice maker
Kitchen island
Microwave
Oven
Refrigerator
Spices
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

Smoke-free property

Services and conveniences

Change of bedsheets (on request)
Change of towels on request
Concierge services
Iron/ironing board
Limited housekeeping
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
Snorkelling 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 organised tours and activities
Towels (changed on request)
Water dispenser

Similar properties

Washing machine
Dryer
Pet-friendly
Air-conditioning

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Policies

Check-in

Check-in time starts at 5:00 PM

Contactless check-in and check-out are 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

Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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

On-site 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 that there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a deadlock

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

Property is also known as

1708-257540

About the area

Located in Islamorada, this holiday home is on the beach. The area's natural beauty can be seen at John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park, while Old Road Gallery and History of Diving Museum are cultural highlights. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and hiking. Visit our Islamorada travel guide

View more Holiday homes in Islamorada

Islamorada, FL

What's nearby

Founders Park
3 min drive - 2.4 km
Theater of the Sea
9 min drive - 7.6 km
Bud n' Mary's Dive Center
22 min drive - 17.2 km
$Anne\'s Beach featuring general coastal views$
Anne's Beach
36 min drive - 29.3 km
Old Road Gallery
15 min walk - 1.3 km

Restaurants

McDonald's
6 min drive
Circle K
8 min drive
Dillon's Pub & Grill
6 min drive
Hog Heaven
6 min drive
Dairy Queen
7 min drive

Frequently asked questions

Does Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 pet-friendly?

No, pets are not allowed at this property.

How much is parking at Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10?

On-site parking is available at the property.

What time is check-in at Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10?

Check-in begins at 5:00 PM.

What time is check-out at Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10?

Checkout is at 9:00 AM.

Where is Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 located?

Nestled on the beach, this Islamorada holiday home is within 2 mi (3 km) of Old Road Gallery, Islamorada County Park and Rain Barrel Village. Founders Park and Florida Keys Dive Center are also within 3 miles (5 km).

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

Wonderful

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.

More information

8.8

Cleanliness

9.6

Location

8/10 Good

Paul M.

9 Mar 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic family retreat

Amazing home for a family to enjoy.

Stayed 7 nights in Jan 2025

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kara C.

13 Apr 2025

Amazing Property

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The entire property was absolutely beautiful and the perfect place to spend Spring Break with family. We enjoyed playing cornhole and wiffle ball on the beach and spent a lot of time on the putting green. Our favorite part was the wildlife - we had many visits from the peacocks and saw manatees, stingrays, sharks and much more from the dock. We hope to visit again soon!

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

ryan k.

3 Apr 2024

Klein

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It was great!

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Gern J.

22 Jul 2024

Jaeger/MacKrell family vacation 2024

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is the second time we have rented Pineapple Beach. It’s so amazing each time we have visited. Our families have been vacationing together for some time in many different homes. Pineapple Beach is the one. It’s perfect in every way.

10/10 Excellent

Amanda M.

29 Jun 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Tess B.

2 Feb 2024

Pineapple Beach

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our family had a wonderful stay at this beautiful property and home! Lots of space and activities for all ages. The mini golf was a hit with our teenagers and everyone enjoyed our morning visits from a group of peacocks. Smooth check in / check out process and Keys Ocean Vacation Rentals were quick to answer any questions that we had. Will definitely recommend to others!

10/10 Excellent

MaryBeth C.

30 Aug 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely house on beautiful property. We had a few issues upon arrival but the property manager was extremely helpful and responded to our issues right away. This is a great house for families of all ages and is a good location if you want to explore the entire keys.Only two things to be aware of. One is the Sargassum seaweed that the Atlantic side of the keys gets in the summer. It made it impossible to use the beach at the house or even enter the water from the property. And the smell it emits is aweful. We opted to do some water excursions from the gulf side. The other are the wild peacocks that are all over the area. Not much you can do about them as they seem to love Islamorada and regardless of the property you rent you will have to deal with them. If we decide to come back to the Keys it will be in the winter / spring months and this house would be on our list to rent again.

Stayed 7 nights in Aug 2025

6/10 Okay

Jessy R.

15 Jun 2025

Liked: Location

Disliked: Communication

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