Entire home

Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!

Vacation home in Holmes Beach with a fitness center and an outdoor pool

Photo gallery for Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!

Exterior
Pool
Bathroom
Room
Room

Reviews

9.6 out of 10
Exceptional
4 bedrooms5+ bathroomsSleeps 83600 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, Island Gallery West
    ‪12 min walk‬
  • Place, Holmes Beach Beaches
    ‪17 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪31 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
Dining area

About this property

Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!

Summary:

🍍 Pineapple Paradise is a 4BR/6.5BA luxury home just steps from the beach, perfect for families and groups ☀️. Enjoy a heated pool with water slide, spa, waterfall grotto, poolside bar, games, and a rooftop deck with Gulf views 🌊. Featuring 4 king suites, a bunk loft, spacious indoor/outdoor living, and a prime location near Pine Avenue, this owner-managed retreat offers the ultimate Anna Maria Island escape 🏖️🍹.



The Space:

🍍 Pineapple Paradise – Water Slide, Heated Pool & Spa! 🌊

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 stunning Gulf views ☀️🌅.



✨ Top Highlights

• Private heated pool with water slide & spa 💦

• Waterfall grotto & poolside bar 🍹

• Rooftop deck with Gulf views 🌊

• Outdoor living, dining & grill 🔥

• Foosball, ping pong & Connect 4 🎯

• Steps to the beach & near Pine Avenue 🏖️

• Owner managed for a personal touch



🏡 Stylish & Spacious Interior

Inside, hardwood floors and charming coastal décor create a serene island atmosphere. The fully stocked 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 & 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 & 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 🌴🍔.



📍 Prime 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:

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. 🌴



Other Things to Note:

🏖️ Beach-Ready Convenience 🌴

To make your stay effortless, the home is fully stocked with 6 beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️🐚



🚗 Parking Information

Parking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.



🌙 Friendly Island Reminder

This home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere 🌺



Interaction with Guests:

If you need anything during your stay, I’m here to help! You can call or text me directly on my cell. I’m available 24/7 to answer questions, offer local tips, or assist with anything that comes up. Your comfort is my priority!
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot Tub
Kitchen
Washer
Dryer
Pet friendly

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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 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

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

We should mention

This property does not have elevators

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 Bean Point Beach and Anna Maria Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Take an 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
  • Island Gallery West - 12 min walk - 1.1 km
  • Palmetto Avenue Beach - 15 min walk - 1.3 km
  • Holmes Beach Beaches - 17 min walk - 1.5 km
  • Manatee Public Beach - 3 min drive - 1.8 km

Getting around

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

Restaurants

  • ‪The Ugly Grouper - ‬10 min walk
  • ‪Anna Maria Island Beach Cafe - ‬4 min drive
  • ‪The Sandbar Restaurant - ‬4 min drive
  • ‪Skinny's Place - ‬4 min drive
  • ‪Ginny's & Jane E's - ‬4 min drive

Frequently asked questions

Does Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa! have a pool?

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

Is Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa! 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~WATER SLIDE/ Heated Pool & Spa!?

Check-in begins at 4:00 PM.

What time is check-out at Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa!?

Check-out is at 10:00 AM.

Where is Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa! located?

Situated near the beach, this vacation home is within a 15-minute walk of Bradenton Beach and Island Gallery West. Palmetto Avenue Beach and Holmes Beach Beaches are also within 1 mi (2 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 3 out of 4 reviews
Rating 8 - Good. 1 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

8/10 Good

Nancy B.

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

10/10 Excellent

Rachel M.

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

10/10 Excellent

Dawid W.

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

10/10 Excellent

john B.

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

Rental as described

Excellent stay
Stayed 7 nights in Jul 2025

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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