House - Rating 5 (20)

Pineapple Key


Bedroom 4 bedrooms
Bathroom 2 baths
Guests 8 guests
Pets Not Allowed Pets Not Allowed

  • Address: 4505 Gulf Dr
  • Location: Holmes Beach
  • Type: House

Location Location

Description Description
Pineapple Key by Anna Maria Vacations
4505 Gulf Dr, Holmes Beach, FL 34217
VRC16-000364

Welcome to Pineapple Key, a charming beach house just minutes from the sugar-white sands of the Manatee Beach! This beautifully landscaped four-bedroom, two-bath home features a private pool, in-ground spa, and tropical outdoor living spaces, making it ideal for friends and family gatherings. Located within walking distance of the beach, shops, and restaurants, Pineapple Key embodies relaxed island living with all the comforts you need for a memorable Anna Maria Island escape!

Highlights
• 3-minute walk to Manatee Public Beach
• 4 Bedroom / 2 Bath
• 2 Kings, 1 Queen, 2 Twin-over-twin bunks plus trundle
• Private pool and in-ground spa
• Outdoor lanai and tiki bar
• BBQ grill
• Pool and Ping Pong Table
• Wii gaming system
• Short walk or trolley ride to shops, waterfront dining, and local attractions
• Washer and dryer
• 8 Parking Spaces

Step inside Coastal Comfort, where vibrant coastal decor and relaxed island vibes create the perfect backdrop for your beach getaway. The main living area features a spacious layout with a large sectional sofa, cozy chairs, and a smart TV, ideal for movie nights or relaxing after a day on the sand. A second living room offers a more intimate retreat, complete with its own sectional, TV, and Wii gaming system, providing a fun hangout spot for kids or an extra lounge area for guests.

The fully equipped kitchen is designed for convenience with high-end appliances, ample counter space, and all the cookware needed to prepare your favorite meals. Gather for casual breakfasts or family dinners in the open dining area or step out to the covered lanai for outdoor dining and a true taste of island living.

This home offers a thoughtful layout with two bedrooms and a shared bathroom on each side, ideal for couples traveling together or families seeking both comfort and privacy. On the East Side, you’ll find a serene king bedroom with crisp linens and a shared bathroom featuring a walk-in shower, along with a cozy queen bedroom nearby. The West Side includes another king bedroom with a premium mattress and coastal decor, plus a fourth bedroom designed with families in mind featuring two sets of bunk beds and a trundle bed. A shared bathroom with a shower/tub combination provides added comfort and flexibility for all guests.

Room Details
• Primary Bedroom: Queen bed, ensuite bathroom
• Second Bedroom: King bed
• Third Bedroom: King bed
• Fourth Bedroom: Twin-over-twin bunk beds

Book Pineapple Key today and enjoy an unforgettable getaway on Anna Maria Island. With its beautiful water views, private pool and spa, outdoor entertainment, and nearby beaches, this home offers everything you need for a relaxing and memorable escape!


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This property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high quality linens; including bedding, bath towels, wash cloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

This home is managed by Anna Maria Vacations, an Anna Maria Island property management company.

8 cars maximum are able to park at this home. 2 parking spaces are covered while the additional 6 are uncovered. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

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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Swipe Swipe for Availability

Bedding Bedding
Bedroom 1
1 Queen

Attached Bathroom

Bedroom 2
1 King

Bedroom 3
1 King

Bedroom 4
2 Twin over Twin Bunk Bed with Twin Trundle


Amenities 67 Amenities
Essentials
  • Air Conditioning
  • Beach Towels Included
  • Bed Linens
  • Dryer
  • Free Wifi
  • Hair Dryer
  • Heating
  • Hospital Close By
  • Hot Water
  • Long Term Stays Allowed
  • No Pets Allowed
  • Private Entrance
  • Towels
  • Washer
  • Wifi
Exterior
  • Backyard
  • Balcony
  • BBQ Grill
  • Covered Deck
  • Fenced Yard
  • Heated Pool
  • Hot Tub or Spa
  • Outdoor Dining Area
  • Outdoor Seating
  • Private Pool
  • Sun Loungers
  • Tiki Bar
Fun and Entertainment
  • Foosball
  • Pool Table
  • Smart TV
  • TV
  • Video Game Console
Home Safety
  • Carbon Monoxide Detector
  • Contactless Check-In
  • Deadbolt Lock
  • Fire Extinguisher
  • Keyless Lock
  • Outdoor Lighting
  • Smoke Detector
Interior
  • Bathtub
  • Ceiling Fans
  • Full Kitchen
  • Living Room
Kitchen
  • Baking Sheet
  • BBQ Utensils
  • Blender
  • Coffee Maker
  • Dining table
  • Dishes and Utensils
  • Dishwasher
  • Freezer
  • Hot Water Kettle
  • Keurig Coffee Maker
  • Microwave
  • Oven
  • Pots and Pans
  • Refrigerator
  • Stove
  • Toaster
  • Wine Glasses
Location
  • Anna Maria Island
  • Beach Access Nearby
  • Holmes Beach
  • Residential Street
  • Walking Distance to Beach
Parking
  • Covered Parking
  • Three (3) Parking Spaces

Reviews Rating 5 (20) Reviews
Rating 5
Our check in process was smooth, and all communication with the property management company was fast and easy. For example, we asked for early check in and needed the propane refilled and they responded right away. The place itself is great, exactly as shown in the photos. It's a 3 minute walk to the beach. The place cam weel stocked with kitchen supplies and tons of beach gear and toys. We were happy with our stay and would stay again!
Angela - Posted: 3/27/2025
Rating 5
Great location and stay!
Our check in process was smooth, and all communication with the property management company was fast and easy. For example, we asked for early check in and needed the propane refilled and they responded right away. The place itself is great, exactly as shown in the photos. It’s a 3 minute walk to the beach. The only downside is that the house is on a busy road and you can hear cars passing late at night and early in the morning.The place came well stocked with kitchen supplies and TONs of beach gear and toys. The one thing that was missing from the listing is that it does have a washer and dryer, which was a huge plus (at the time we booked, the listing only mentioned laundry nearby). I hope they update the listing with this info as we almost decided to pass because of this. Overall we were happy with our stay and would stay again!
Angela - Posted: 3/26/2025
Rating 5
We had a great stay here. Property was exactly how it was listed and it was in a great location. Pool and hot tub was very nice and was a hit with our teenage daughters.
Jeff - Posted: 3/14/2025
Rating 5
Very casual and relaxing
We had a great stay here. Property was exactly how it was listed and it was in a great location. Pool and Hot tub was very nice and was a hit with our teenage daughters
Jeff - Posted: 3/9/2025
Rating 5
Lawrence H. - Posted: 3/7/2025
Rating 5
House was clean and well stocked. Love the pool!
Anonymous - Posted: 2/26/2025
Rating 5
We had an amazing week here! Our children loved the pool and hot tub! Plenty of games and activities for the kids. Great location. House worked perfectly with the 2 living spaces. So close to the beach, we walked there every day. We hope to go back again!
Anonymous - Posted: 2/26/2025
Rating 5
Nice house
House was clean and well stocked. Love the pool!
Robert P. - Posted: 2/24/2025
Rating 5
We had an amazing week here! Our children loved the pool and hot tub! Plenty of games and activities for the kids, GREAT location. House worked perfectly with the 2 living spaces. So close to the beach, we walked there every day. We hope to go back again!
Rosanne Grace - Posted: 12/31/2024
Thank you so much for the wonderful review! We are delighted to hear that you and your family had an amazing time and enjoyed all the amenities our property has to offer. It's great to know that the house layout and the proximity to the beach were a perfect fit for your needs. We truly appreciate your kind words and look forward to welcoming you back in the future.
Prime Vacations staff
Rating 5
Pineapple key at AMI
Property was beautiful and had everything we needed plus more. The pool was perfect for entertaining the kids and lots of gaming options for the adults as well. The property was very clean and well prepared for guests.
Jayln S. - Posted: 6/16/2024
Rating 5
We had a great time! The location was great. The pool and spa were a hit with everyone. The 2 living spaces were nice. We kept the kids upfront in the bunk room and the adults too the back two rooms. There really isn't a master suite. The bathrooms are in hallways which made it easier to use either one. The beach carts were great to have even though the walk was maybe 5 minutes at the most. We had a great time and would love to stay there again.
Anonymous - Posted: 5/2/2024
Rating 5
Great beach house
We had a great time! The location was great. The only draw back was trying to exit the driveway with cars on the main road. The cars yield to walkers but getting out with the car took some time depending on traffic. The pool and spa were a hit with everyone. The 2 living spaces were nice. We kept the kids up front in the bunk room and the adults too the back two rooms. There really isn’t a master suite. The bathrooms are in hallways which made it easier to use either one. The beach carts were great to have even though the walk was maybe 5 minutes at the most. We had a great time and would love to stay there again.
Robert W. - Posted: 4/28/2024
Rating 5
Great location -close walk to the most beautiful beach!! The private wading pool was clean and refreshing. The home has been updated with beautifully decorated king bedrooms and one bunk room-tv in each room. We walked to restaurants and to marina daily. The trolley stop is with In a block and the kids enjoyed jumping on it to tour the island. We will be back next year for sure!! Thank you!
Anonymous - Posted: 1/8/2024
Rating 5
Anna Maria island
We were very pleased with everything. The kitchen was well equipped( but you may want to get better knives for chopping etc, I would also have liked a few more hand towels and wash clothes( only 2 for 8 people). Location was perfect as was the beach!
patrice p. - Posted: 11/25/2023
Rating 5
Great House
We had 4 couples at Spring Break and the house was awesome. Plenty of room, well equipped, clean and really close to the beach. By well equipped I mean not only the kitchen, but there is a closet downstairs with chairs, umbrellas, games, floats, even a metal detector (needs 2 (v batteries). When we weren't at the beach (mornings and evenings) we were downstairs having pool (i.e. billiard) tournaments, hanging out in the pool or hot tub and grilling. We would rent this house again if it available. Beach is 2 minutes away the way I walk, if you walk really slow maybe 5 minutes.
Thomas P. - Posted: 4/20/2023
Rating 5
We had 4 couples at Spring Break and the house was awesome. Plenty of room, well equipped, clean and really close to the beach. By well equipped I mean not only the kitchen, but there is a closet downstairs with chairs, umbrellas, games, floats, even a metal detector (needs 2 (v batteries). When we weren't at the beach (mornings and evenings) we were downstairs having pool (i.e. billiard) tournaments, hanging out in the pool or hot tub and grilling. We would rent this house again if it available. Beach is 2 minutes away the way I walk, if you walk really slow maybe 5 minutes.
Anonymous - Posted: 4/20/2023
Rating 5
We stayed here 1 week and had a great time!! They regularly cleaned the pool throughout the week for us and the hot tub was amazing. Also, all the pool toys they had were great for the kids!! When we showed up everything was clean and in great condition! Initially there was issues with the door code password not working but with one quick phone call the issue was resolved. The location is nice as well! You walk across gulf drive and in a block you’re at a pristine beach! Having two parking spots was also excellent! Great stay!! Great family destination!!
John - Posted: 1/20/2023
John, thank you for taking the time to share your experience with us. We are glad you enjoyed the home, pool, hot tub, and location. We hope to host you again sometime in the future!
Prime Vacations staff
Rating 5
Great beach house
The house had everything you need for a beach location. Pool was fun and outdoor area was well laid out with bar-b-q, table, etc. Appreciated the beach chairs and cooler. The two living areas of the house were perfect for the two families staying with us.
Cynthia H. - Posted: 10/20/2022
Rating 5
A casa é ótima, com toda infraestrutura para aproveitar as férias … praia lindas próximas….
Dangelo - Posted: 9/25/2022
Dangelo, we are happy to hear you enjoyed your stay and the location. We hope to host you again soon!
Prime Vacations staff
Rating 5
This vacation rental is top notch and has everything you need for a week on AMI! The downstairs area with pool, jacuzzi, dining, lounging pool table and grill makes entertaining easy. Just across the street to the beach and the trolley stops right in front of the place for shuttling up/down the island. Everything you need is at Pineapple Key AMI!!!
Anonymous - Posted: 8/26/2022
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