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Pineapple Paradise ~ Pool Slide ~ Rooftop

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A two-story house with a swimming pool, a waterfall feature, and a balcony with a white railing.
A two-story house with a balcony, garage doors, and a number '207' on the front.
A covered outdoor area with a white spiral staircase leading to a balcony, surrounded by lush greenery.
A modern kitchen with a central island, pendant lighting, and a dining area with a sofa and chairs.
A modern kitchen with white cabinetry, stainless steel appliances, and pendant lighting.

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms6 bathrooms3600 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Holmes Beach, FL
  • Place, Bradenton Beach
    ‪2 min walk‬
  • Place, Manatee Public Beach
    ‪2 min drive‬
  • Place, Holmes Beach Beaches
    ‪7 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪37 min drive‬

Room options

Similar properties

About the neighborhood

Holmes Beach

When you stay at this vacation home in Holmes Beach, you'll be near the beach, a 3-minute drive from Bradenton Beach and 6 minutes from Bean Point Beach. .This vacation home is 11 mi (17.8 km) from IMG Academy and 19.3 mi (31.1 km) from Tampa Bay.

What's nearby

  • Bradenton Beach - 2 min walk - 0.1 miles
  • Manatee Public Beach - 2 min drive - 1.1 miles
  • West Coast Surf Shop - 3 min drive - 1.5 miles
  • AMI Paddleboard Adventures - 3 min drive - 1.5 miles
  • Holmes Beach Beaches - 7 min drive - 1.3 miles

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 43 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬4 min drive
  • ‪Anna Maria Island Beach Cafe - ‬4 min drive
  • ‪The Ugly Grouper - ‬10 min walk
  • ‪Ginny's & Jane E's - ‬4 min drive
  • ‪The Waterfront Restaurant - ‬6 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 Paradise ~ Pool Slide ~ Rooftop

Summary:

🌓 Make the most of days outdoors at Pineapple Paradise, with a heated pool, waterslide, waterfall grotto, and spa. Gather by the poolside bar, enjoy a game together, or take in Gulf views from the rooftop deck. Spacious indoor and outdoor living areas keep everyone comfortable between beach outings.



The Space:

Pineapple Paradise – Water Slide, Heated Pool and Spa.



VRC #: VRC19-000039



Welcome to Pineapple Paradise, an exceptional 4-bedroom, 6.5-bath luxury retreat just steps from the beach and designed for unforgettable island fun. Perfect for families, couples, and multi-generational groups, this owner-managed home features an incredible backyard water paradise and a rooftop deck with Gulf views .



Top Highlights



• Private heated pool with water slide and spa



• Waterfall grotto and poolside bar



• Rooftop deck with Gulf views



• Outdoor living, dining and grill



• Foosball, ping pong and Connect 4



• Steps to the beach and near Pine Avenue



• Owner managed for a personal touch



Stylish and Spacious Interior



Inside, hardwood floors and charming coastal dĆ©cor create a serene island atmosphere. The well-equipped kitchen features modern appliances, ample cookware, island seating, and a formal dining table—perfect for shared meals . After a day of adventure, relax on the plush sofas and enjoy movie night .



Private Suites and Flexible Sleeping



Ideal for large groups, each bedroom offers privacy and comfort:



• Primary Suite (3rd Floor): King bed, private balcony, rooftop access, ensuite with double vanity and walk-in shower



• 3 King Guest Suites: Each with private balcony, TV, and ensuite bath



• Loft (3rd Floor): 4 twin bunk beds + 2 full bathrooms—perfect for kids



A half bath and laundry room are conveniently located downstairs .



Ultimate Outdoor Oasis



Step outside to your own tropical playground featuring a heated pool, in-ground spa, thrilling water slide, and waterfall grotto . Enjoy poolside dining, fire up the grill, or relax at the bar with a TV—perfect for entertaining day or night .



šŸ“ ISLAND LOCATION



Located near the beach and just minutes from Pine Avenue’s charming shops and restaurants, everything is easily accessible by bike or the free AMI trolley .



Come experience island luxury, endless fun, and laid-back vibes at Pineapple Paradise—your dream vacation starts here.



Guest Access:

šŸ”‘ Guest Access



Guests have full access to the entire home, including a private heated poo/spa, waterslide, and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space. 🌓



The Neighborhood:

šŸ“ The Neighborhood



Enjoy Holmes Beach on Anna Maria Island, with Gulf beaches and local island shops and dining. Explore the island’s three communities—Anna Maria, Holmes Beach, and Bradenton Beach—at your own pace.



Getting Around:

šŸš— Getting Around



Use the arrival directions provided before check-in and follow the parking instructions for this property. Use designated public beach access points and marked crossings when heading to the beach.



Other Things to Note:

🧻 Starter Supplies



To help you get settled in, we provide a complimentary starter supply of essentials upon arrival:



☼ Two (2) rolls of toilet paper per bathroom



☼ One (1) roll of paper towels in the kitchen



☼ Two (2) dishwasher pods



☼ One (1) small bottle of dish soap



☼ One (1) trash bag per trash can



☼ Shampoo, conditioner, and body wash in every bathroom



Additional supplies may be needed depending on the length of your stay.



šŸ–ļø BEACH AMENITIES INCLUDED



☼ Every home is stocked with beach essentials for your convenience:



☼ Beach towels for all registered guests



☼ Beach wagon



☼ 4 beach chairs



☼ Beach umbrella



☼ Cooler



☼ 🐾 Pet Policy



Dogs only with prior approval.



☼ Maximum 25 pounds per dog



☼ Non-shedding breeds only



☼ $200 pet fee per stay for approved dogs



Cats and other animals are not permitted.



šŸš— Parking



Parking is available for up to 6 vehicles in the driveway. Please coordinate with your group before arrival, as overnight parking is not available for additional vehicles.



šŸ‘¤ Age Requirement



We do not accept reservations from guests under 25 years of age. At least one guest occupying the property must be 25 years of age or older.



🤫 Noise Ordinance



This home is located in a residential neighborhood. Please be respectful of neighboring properties and comply with local noise ordinances.



☼ Additional Property Information



Quiet hours: 10:00 PM to 8:00 AM.



At least one guest must be 25 years of age or older and remain at the property throughout the reservation.



Interaction with Guests:

šŸ’¬ Here to Help



Please message us through your booking platform with questions before or during your stay. Our team can help with property information, local recommendations, and anything that needs attention at the home.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected.
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. This vacation home also features barbecue grills and bike storage.
Featured amenities include laundry facilities and a water dispenser.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster
  • Water dispenser

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 5.5 bathrooms
  • Hair dryer
  • Shampoo
  • Shower

Living spaces

  • Dining table

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 20 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Gravel flooring in public areas
  • Handrails in stairways
  • Smooth flooring in public areas
  • Tile flooring in public areas
  • Upper floors accessible by stairs only
  • Smoking not allowed

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Things to do

  • Bicycle parking
  • Bicycle storage
  • Heated pool
  • Scuba diving nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Bicycle parking
  • Bicycle storage
  • Double-glazed windows
  • Garden
  • Housekeeping (on request)
  • Locally-owned and organized tours and activities
  • Recycling
  • Some LED lighting used
  • Unit size: 3,600 square feet
  • Water dispenser usage encouraged

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

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

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels and store extra beds
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights and lock the doors
Thank you for staying with us at Pineapple Paradise! We hope you had the 5-star experience that we strive to provide you!
If you plan to leave before 10am, please let us know so we can schedule the cleaners. There is no need to strip the beds or wash the towels; our cleaning crew will handle that.
Loading the dishwasher would be very helpful. We hope you enjoyed your stay & look forward to hosting you again soon!
Failure to complete these may result in a negative review from the host.

Rules

4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight pa...
Please Remember: Please be a good neighbor by keeping noise to a respectful level during the day and night. Quiet time 10pm-8am Island Wide.
We don't accept reservations from anyone under 25 years old. We don't allow persons under 25 to occupy property unless accompanied by someone over 25

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 20 lbs per pet)

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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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

We should mention

This property does not have elevators

Property is also known as

690a2d2daca3d9003bda80c7

Pineapple Paradise ~ Pool Slide ~ Rooftop Reviews

Reviews

9.8

Exceptional

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

9.8/10

Cleanliness

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The pool was very nice.
Stayed 7 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had such a good time at the Pineapple Paradise! Great location, awesome pool, spa and water slide. Our host Jennifer was very great and ensured the house had everything we needed. Definitely would stay here again!
Stayed 7 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I cannot say enough positive things about this rental. It was truly amazing and had everything you could possibly need, just like being at home. The location was perfect, with less than a one minute walk to the beach. My family and I had absolutely no complaints and enjoyed every minute of our stay. It was a wonderful vacation experience from start to finish.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our favorite house! It was perfect for multiple families staying together. So much space for the kids and the pool was a huge hit with everyone.
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

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

Rental as described

Excellent stay
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House had everything and more.Best time for the kids and adults.Really close to the beach.
Stayed 7 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a small hiccup upon arrival, but Jen handled it right away—such great service! The home itself is absolutely beautiful, with plenty of space for everyone to relax comfortably. The pool was perfect for unwinding, and we loved how it was just a short walk to the public beach access. Booking was easy and seamless from start to finish.We can’t wait to come back—AMI truly is an amazing destination! Thank you, Jen, for being such a wonderful host and making our stay so enjoyable.
From the roof balcony!
Pool
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay at Pineapple Paradise! Jennifer was very helpful and accommodating-we had a minor maintenance need when we arrived and Jen had someone there within the hour to address. The home is very nicely decorated throughout giving you the feeling of vacation and relaxation. Kitchenware is plentiful with everything we needed for eating in. And the pool with the slide and hot tub is pretty cool too! Very short walk to beach - great location!
Stayed 28 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect for all 9 of us! Spacious, clean, everything we needed and more, the pool area was a lot of fun and the walk to the beach was very close! Would definitely rent again
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great experience overall.
Stayed 7 nights in Jun 2026