Entire home

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

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Bradenton Beach
4 bedrooms5+ bathroomsSleeps 8

Popular amenities

  • Balcony
  • Hot tub on site
  • Private pool
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning

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

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

5 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Bathtub · Toilet · Shower only

Bathroom 4

Bathtub · Toilet · Shower only

Bathroom 5

Bathtub · Toilet · Shower only

Bathroom 6

Toilet

Spaces

Kitchen
Balcony
Garden

About this property

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 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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 9 kg per pet (limit 2 pets total)
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to 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 rubbish
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 # 4649979vb
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
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Holmes Beach

Located in Holmes Beach, this holiday 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 the opportunity to explore the area for water adventures such as scuba diving.
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 2 min walk - 0.2 km
  • Manatee Public Beach - 2 min drive - 1.8 km
  • West Coast Surf Shop - 3 min drive - 2.4 km
  • AMI Paddleboard Adventures - 3 min drive - 2.4 km
  • Holmes Beach Beaches - 7 min drive - 2.1 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 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 22 Oct, 2026, prices found for a 1-night stay for 2 adults at Pineapple Paradise ~ Pool Slide ~ Rooftop on 24 Oct, 2026 start from S$5,243, 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 9 kg 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?

Checkout is at 10:00 AM.

Where is Pineapple Paradise ~ Pool Slide ~ Rooftop located?

Situated near the beach, this holiday home is within 1 mile (2 km) of Bradenton Beach and Holmes Beach Beaches. Manatee Public Beach and West Coast Surf Shop are also within 2 miles (3 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

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
Response from VrboOwner on 14 Oct, 2025
Nancy was a wonderful guest! She is welcome back anytime!
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
Response from VrboOwner on 22 Oct, 2025
Hi Rachel! We are so glad you had a wonderful stay! We would love to have you and your family back anytime!
Verified review

10/10 Excellent

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

Rental as described

Excellent stay
Stayed 7 nights in Jul 2025
Response from VrboOwner on 22 Jul, 2025
We are so happy you had a great stay! We would love to have you back anytime 🌴
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

About the host

Hosted by Jennifer Kaleta

Host profile image
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

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