Blue Pineapple Vacation Rental With Private Pool Near Gulf Beaches
Home Rental in Holmes Beach Florida
Three-level 4-bedroom home in Holmes Beach with a private heated pool, elevator, and balconies, a practical place to stay near the Gulf and the Anna Maria Island trolley for dining and shops.
Why You'll Love This Rental
Blue Pineapple is a three-level home in Holmes Beach, Florida, set near the waterfront and near a beach. With 4 bedrooms, 2.5 bathrooms, and sleeping for up to 8 guests, it’s designed for a comfortable island stay with standout features that include a private pool, multiple balconies, and an elevator. The home is also dog-friendly with host approval and an additional pet fee, and it offers parking for up to four vehicles.
Inside, the layout centers on an open living area and a full kitchen with an island, supported by practical essentials such as Wi-Fi, washer/dryer, towels/linens, and a range of small appliances including a Keurig coffee maker and hot water kettle. Outdoor living is a key part of the experience, with a covered patio, grill, outdoor seating, sun loungers, and an outdoor shower for rinsing off after beach time. Sleeping options include two king beds, one queen bed, and a twin-over-twin bunk bed, with the primary suite located on the third floor and featuring an ensuite bathroom and balcony access.
Property Highlights
Blue Pineapple is located in Holmes Beach, Florida, on Anna Maria Island in the South Gulf Coast region. The home is listed as waterfront-nearby and near a beach, and the source notes a nearby Anna Maria Island trolley stop for getting around the island. The property is in a residential street setting, and guests are asked to keep noise to a respectful level in consideration of neighbors.
Rates & Availability (USD)
Live booking details are maintained by AMI Locals.
Availability Calendar
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About This Rental
CAA20-000023
Welcome to Blue Pineapple by AMI Locals, a stylish 4-bedroom, 2.5-bathroom island retreat just a 3-minute walk from the Gulf beaches of Holmes Beach. This beautiful three-level home combines tropical charm and modern comfort with a private pool, covered patio, and multiple balconies perfect for catching the island breeze. The Anna Maria Island trolley stop is just steps away, providing easy access to local restaurants, boutiques, and Old-Florida coastal adventures.
Highlights
• 3-minute walk to the beach
• 4 Bedrooms / 2.5 Bathrooms
• 2 King beds, 1 Queen bed, 1 Twin-over-Twin bunk bed
• Private pool and covered patio
• Elevator and outdoor shower
• BBQ grill and balcony dining area
• Near free Anna Maria Island trolley stop
• Dog-friendly with host approval and pet fee
• 4 parking spaces
Spend your days soaking up the sunshine in your private backyard oasis, complete with a heated pool, outdoor lounge chairs, and a covered patio perfect for relaxing in the shade. Fire up the BBQ grill for family cookouts or enjoy coffee and card games at the outdoor dining table. Between dips in the pool, rinse off in the outdoor shower, then unwind on one of the balconies as the evening breeze drifts through the palms.
Step inside and feel instantly at home in the bright, open concept living area, furnished with coastal decor and three comfy sofas for movie nights or afternoon naps. The kitchen features granite countertops, stainless steel appliances, a pantry for storing groceries, and a central island with bar seating, ideal for breakfast or meal prep. Just beside it, a formal dining table welcomes family dinners and laughter after a day at the beach.
Take the elevator or stairs to the third floor, where the primary suite offers peaceful comfort with a king bed, private balcony, walk-in closet, and a luxurious ensuite bathroom featuring a double vanity and walk-in shower. The second bedroom has a king bed, and the third bedroom features a queen bed; both with TVs and closet space. They share a hallway bathroom with a shower/tub combination. On the main living floor, the fourth bedroom includes a twin-over-twin bunk bed, balcony access, and easy entry to the half bathroom.
Room Details
-Primary Bedroom (3rd Floor): King bed, balcony access, ensuite bath with walk-in shower
-Second Bedroom (3rd Floor): King bed, shares hall bath
-Third Bedroom (3rd Floor): Queen bed, shares hall bath
-Fourth Bedroom (2nd Floor): Twin-over-Twin bunk bed, balcony access, near half bath
Enjoy the convenience of Wi-Fi, a washer and dryer, and parking for four vehicles. Blue Pineapple is perfectly positioned for exploring Holmes Beach and Anna Maria Island’s local restaurants and cafes, all within walking distance or a quick trolley ride away. Favorites like The Ugly Grouper and Scott's Deli offers delicious coastal fare just minutes from your doorstep. With host approval before check-in, dogs are welcome.
Whether you’re lounging by the pool, barbecuing under the palms, or catching a sunset from your balcony, Blue Pineapple by AMI Locals captures the relaxed elegance of Anna Maria Island vacation living. This home offers style, comfort, and a location that puts the best of Holmes Beach right at your fingertips.
Your tropical escape awaits, book your stay at Blue Pineapple by AMI Locals today!
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*Please note: 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 parking available for additional vehicles.
With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our AMI Locals Rental Policies for full details.
This home is managed by AMI Locals, an Anna Maria Island property management company.
We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.
Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property."*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
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