🌴 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 décor 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 .
📍 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:
🔑 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:
📍 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:
🚗 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
☼ Starter laundry supplies for one load
Additional supplies may be needed depending on the length of your stay.
☕ COFFEE
The kitchen includes both a Keurig and a regular drip coffee maker. Coffee filters are provided.
🏖️ 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
🏊 POOL & PROPERTY DETAILS
The pool is heated to 85°F at no additional charge. Required pool-door alarms must remain active and should not be disabled. No security cameras are installed at the property.
🐾 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.
🚗 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.
👤 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:
💬 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.
Our prices include all fees. No hidden fees.
Add dates for prices
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Pets allowed: dogs less than 20 lbs per pet (limit 2 pets total)
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Smoking
Smoking is not permitted
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.
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
Important information
You need to know
Property # 4649979
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
About the neighborhood
Holmes Beach
Located in Holmes Beach, this vacation home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Fish Hole Adventure Golf and Florida Maritime Museum at Cortez are also worth visiting. Take an opportunity to explore the area for water adventures such as scuba diving.
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
Frequently asked questions
Does Pineapple Paradise ~ Pool Slide ~ Rooftop have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Pineapple Paradise ~ Pool Slide ~ Rooftop?
As of Oct 22, 2026, prices found for a 1-night stay for 2 adults at Pineapple Paradise ~ Pool Slide ~ Rooftop on Oct 24, 2026 start from $527, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Pineapple Paradise ~ Pool Slide ~ Rooftop pet-friendly?
Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 20 lbs per pet.
What time is check-in at Pineapple Paradise ~ Pool Slide ~ Rooftop?
Check-in begins at 4:00 PM.
What time is check-out at Pineapple Paradise ~ Pool Slide ~ Rooftop?
Check-out is at 10:00 AM.
Where is Pineapple Paradise ~ Pool Slide ~ Rooftop located?
Situated near the beach, this vacation home is within 1 mi (2 km) of Bradenton Beach and Holmes Beach Beaches. Manatee Public Beach and West Coast Surf Shop are also within 2 mi (3 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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!
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.
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.
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!
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
My name is Jennifer and I am a mom to 5 kids. I have lived on Anna Maria for the last 20 years! All of the homes are my site are my own homes that I self manage. I love self managing the homes to make sure that you get the ultimate vacation that you are paying for and that you deserve! Whether it is recommendations, questions, or anything that may arise I am personally here for you 24/7.
Why they chose this property
I chose this vacation rental because of its unbeatable location—just 1.5 blocks from the beach, or a 2-minute walk to the sand and surf. It offers the perfect balance of convenience and comfort: close enough to enjoy spontaneous beach trips, yet nestled in a quiet, welcoming neighborhood that feels like a true getaway.
Whether it's morning walks along the shoreline, sunset views, or quick trips back to freshen up, the proximity makes beach life easy and enjoyable. The neighborhood also has a relaxed, local vibe with nearby cafes, shops, and everything you need within walking distance—making it ideal for both relaxation and adventure.
What makes this property unique
What Makes This Property One of a Kind Welcome to your perfect beach getaway—just 1.5 blocks from the sand and packed with amenities that make this vacation home truly unique. Whether you're planning a family trip, group retreat, or coastal escape with friends, this property offers something for everyone:
🌊 Steps from the beach – Only a 2-minute walk to the shore for sun, surf, and sunsets. 💦 Heated pool and spa – Relax and unwind in your own private oasis after a day in the sun. 🎉 Private waterslide – A favorite for kids and kids at heart—make a splash without ever leaving home. 🏓 Game-ready fun – Challenge your group to friendly matches of ping pong or foosball in the game area. 🛏 En-suite bathrooms in every bedroom – Enjoy privacy and comfort with a full bathroom in each sleeping space. 🧺 Professional linen service – Arrive to crisp sheets, plush towels, and fresh, hotel-quality bedding. 🚎 Trolley stop at the end of the road – Hop on for easy, car-free access to local shops, restaurants, and attractions. From unbeatable location to resort-style amenities, this home offers the ultimate blend of convenience, comfort, and fun—all just steps from the beach.
Languages:
English
Premier Host
They consistently provide great experiences for their guests