Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!

Top rated by guests
Exterior
Living area
Private kitchen
Private kitchen
Interior
review stars
9.8Outstanding
(10 Ratings)
"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 perf..."
Jennifer F.
Don't miss out! Price and availability may change
9.8 / 10
Outstanding(10 Ratings)

House in Holmes Beach, FL

8 guests · 4 bedrooms · 5 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

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:

🌴 Everything You Need for a Relaxing Island Stay



☀️ Starter Supplies

To help you settle 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

🧼 Two (2) dishwasher pods

🫧 One (1) small bottle of dish soap

🗑️ A Box of 10 trash bags

🛁 Shampoo, conditioner, and body wash in every bathroom Additional supplies may be needed depending on the length of your stay.



🏖️ Beach-Ready Convenience Spend less time packing and more time relaxing!

Every home is stocked with:

🌊 Beach towels for all registered guests

🛒 Beach wagon

🪑 One (1) beach chair per bedroom

⛱️ Beach umbrella

🧊 Cooler Just pack your swimsuit and enjoy the island!



☀️🐚 🐶 Pet Policy Dogs are welcome with prior host approval.

🐾 Maximum of 25 lbs per dog

🐾 Non-shedding breeds only

💲 $200 pet fee per approved dog

🚫 Cats and all other animals are not permitted.



🔞 Age Requirement At least one guest must be 25 years of age or older and remain at the property throughout the reservation. We do not accept reservations from guests under 25 years of age.



🚗 Parking Information 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.



🌙 Friendly Island Reminder 🏡 This home is located in a peaceful residential neighborhood. Please be respectful of our neighbors by keeping noise to a minimum, especially during Anna Maria Island's quiet hours from 10:00 PM to 8:00 AM. Thank you for helping preserve the relaxing island atmosphere for everyone! 🌺💙



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!



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!

Amenities at Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!

Non-smoking
Pets allowed
Family friendly

Map of Holmes Beach, FL


Ratings and reviews

9.8 / 10
Outstanding(10 Ratings)
10 / 10Outstanding·May 2026
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.
10 / 10Outstanding·Feb 2026
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!
10 / 10Outstanding·Feb 2026
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!
10 / 10Outstanding·Nov 2025
House had everything and more.Best time for the kids and adults.Really close to the beach.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Pineapple Paradise~WATER SLIDE/Heated Pool & Spa!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.