Entire home
Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!
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Reviews
9.8 out of 10
Exceptional
4 bedrooms5+ bathroomsSleeps 83600 sq ft
Popular amenities
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~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! 🌊
📍 207 65th St, Holmes Beach
✅ 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 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!
🍍 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! 🌊
📍 207 65th St, Holmes Beach
✅ 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 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!
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
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
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs less than 9 kg per pet (limit 2 pets total)
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.
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
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
We should mention
This property does not have any lifts
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 H2O Watersportz are also worth visiting. Take the opportunity to explore the area for water adventures such as scuba diving.

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 - 2 min drive - 1.8 km
Getting around
Restaurants
- The Ugly Grouper - 10 min walk
- Anna Maria Island Beach Cafe - 4 min drive
- The Sandbar Restaurant - 4 min drive
- Ginny's & Jane E's - 4 min drive
- Skinny's Place - 4 min drive
Frequently asked questions
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 window9.8/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
14 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Oct 2025
10/10 Excellent
Rachel M.
8 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rachel M.
Stayed 7 nights in Sep 2025
10/10 Excellent
Dawid W.
8 Nov, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Dawid W.
Stayed 7 nights in Nov 2025
10/10 Excellent
john B.
21 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rental as described
john B.
Stayed 7 nights in Jul 2025
10/10 Excellent
Jeff I.
14 Feb, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jeff I.
Stayed 7 nights in Feb 2026
10/10 Excellent
John J.
10 Feb, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy

John J.
Stayed 28 nights in Jan 2026
About the host
Hosted by Jennifer Kaleta
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.
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.
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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