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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.

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AMI Locals
Connect directly with the local vacation rental manager.
Rates from
$175 / night
Additional fees may apply
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Rental overview

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.

Good fit for
Pet-friendly stays Long-term stays
Private pool Enjoy a private pool plus outdoor seating and sun loungers in the fenced yard.
Elevator access Three-level home includes an elevator for moving between floors.
Dog-friendly stay Dogs are allowed with host approval before check-in and an additional pet fee.
Outdoor shower Outdoor shower is available for rinsing off after beach time.
Parking for four Parking is limited to four vehicles total, including two garage spaces.
At a glance

Property Highlights

Waterfront - NearbyLocation Setting
Near a BeachBeach Access
4 BedroomsBedrooms
2 Full, 1 Half BathroomsBathrooms
Sleeps 8Guest Capacity
1967 sq. ft.Living Space
Pool (Private)Pool
Internet AccessInternet
TelevisionTelevision
YesAir Conditioning
YesPet Friendly
YesWasher / Dryer
Location & nearby Explore the Area

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.

Plan your stay

Rates & Availability (USD)

Rates from
$175 per night
7-day minimum stay
Check current rates & availability

Live booking details are maintained by AMI Locals.

Check Availability

Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

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About this rental

About This Rental

Blue Pineapple is a 1,967-square-foot, three-level vacation home in Holmes Beach on Anna Maria Island. It offers 4 bedrooms, 2 full bathrooms, and 1 half bathroom, accommodating up to 8 guests. The setting is listed as waterfront-nearby and near a beach, and the home includes an elevator for easier movement between floors. A private pool anchors the outdoor space, supported by a fenced yard, patio areas, and outdoor seating.

The main living areas are arranged for day-to-day convenience, with a full kitchen that includes a refrigerator, stove, oven, microwave, dishwasher, and ice maker, plus cookware, dishes, and utensils. A kitchen island and dining table provide dedicated spots for meals, while the living room offers a comfortable place to gather. In-home essentials include air conditioning, heating, internet access, televisions, and a washer/dryer. Safety features noted include a fire extinguisher, smoke detector, and carbon monoxide detector.

Bedroom setup includes 2 king beds, 1 queen bed, and a twin-over-twin bunk bed. The primary bedroom is on the third floor with balcony access and an ensuite bathroom with a walk-in shower. Two additional bedrooms on the third floor share a hallway bathroom with a shower/tub combination. The fourth bedroom is on the main living floor with balcony access and is located near the half bathroom.

Outdoor amenities include a grill, outdoor shower, sun loungers, and beach chairs provided. Parking is limited to four vehicles total, including two garage spaces, and long-term stays are allowed. Dogs are permitted with host approval before check-in and an additional pet fee; other animals are not allowed.

Blue Pineapple by AMI Locals
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.
Before you book

Vacation Rental Policies

Check In

4:00 PM

Check Out

10:00 AM

Things to enjoy

Activities and Special Interests

This property provides access to the following activities and special interests:

Fishing
Golfing
Pet Friendly
Family Vacations
Boating
Canoeing
Fly Fishing
Kayaking
Beach
Deep Sea Fishing
Ocean
Surfing
Scuba Diving
Wind Surfing

Other Activities and Special Interests

Museums Nearby
Boating Nearby
Local Eco Tourism Nearby
Horseback Riding Nearby
Outlet Shopping Nearby
Wildlife Viewing Nearby
Fitness Center Nearby
Laundromat Close By
Tennis Court Nearby
Basketball Court Nearby
Hiking Nearby
Jet Skiing Nearby
Parasailing Nearby
Sailing Nearby
Snorkeling Nearby
Surfing Nearby
Swimming Nearby
Health Beauty Spa Nearby
Marina Nearby
Shopping Nearby
Bird Watching Nearby
Kayaking Nearby
Water Sports Nearby
What's included

Property Amenities

Property Features

Full Kitchen
Towels/Linens
Coffee Maker
Hair Dryer
Microwave
Oven
Refrigerator
Stove
Toaster
Balcony
Elevator
Blender
Ceiling Fan(s)
Freezer
Ice Maker

Featured Amenities

Television
Internet Access
Air Conditioning
Dishwasher
Washer/Dryer
Grill
Pool (Private)
Pets Allowed

Other Property Amenities

Holmes Beach
Anna Maria Island
Dishes and Utensils
Fire Extinguisher
Living Room
Clothes Hangers
Heating
Hot Water
Long Term Stays Allowed
Private Entrance
Smoke Detector
Hospital Close By
Carbon Monoxide Detector
Deadbolt Lock
Pots and Pans
Contactless Check-In
Pack 'n Play
Backyard
Iron and Ironing Board
Patio
Residential Street
Fenced Yard
Kitchen Island
Dining Table
Two (2) Garage Spaces
Four (4) Parking Spaces
Bathtub
Keurig Coffee Maker
Outdoor Seating
Outdoor Shower
Clothing Storage
Hot Water Kettle
Sun Loungers
Beach Chairs Provided
Desk
Uncovered Deck
Helpful details

Frequently Asked Questions

Blue Pineapple is located in Holmes Beach, Florida.

Blue Pineapple accommodates up to 8 guests.

4 Bedrooms and 2 Full, 1 Half Bathrooms.

The listed beach access for Blue Pineapple is Near a Beach.

Yes. The property lists Pool (Private).

Yes. Blue Pineapple is listed as pet friendly. Review the manager's policies for any pet restrictions or fees.
Local management

Professionally Managed By

AMI Locals View Manager Profile

Questions about this rental?

Connect directly with AMI Locals for current rates, availability, and local assistance.

Contact Reservations and Guest Services AMI Locals
Daytime Phone
Property reference
#191929 · Blue Pineapple
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