Island Pineapple: Holmes Beach Florida 4 Bedroom Vacation Home for Rent with Pool and just a Quick Walk to the Beach

Island Pineapple: Holmes Beach Florida 4 Bedroom Vacation Home for Rent with Pool and just a Quick Walk to the Beach

Vacation home with pool on Anna Maria Island with 4 bedrooms an easy walk to the beach in Holmes Beach FL : Island Pineapple

Vacation Home in Holmes Beach Florida

404 80th Street
Bedrooms: 4 Bedrooms • Sleeps 8
Bed Arrangements: 2 Twin over Twin Bunk Bed - 1 Queen Bed - 2 King Bed
Bathrooms: 4 Full Bathrooms
Virtual Tour: Island Pineapple - Virtual Tour
Living Space: 2744 sqft.
Location Setting: Waterfront - Nearby
Beach Access: Near a Beach
Air Conditioning: Yes
Pool: Pool (Private)
Internet: Internet Access
Television: Cable/Dish TV
Washer/Dryer: Yes
Map of Holmes Beach

Rates & Availability  
(Displayed in USD)

  • Daily Rates from $260 to $1,270 per night
  • Weekly Rates from $1,750 to $4,550 per week
  • Minimum Stay: 7 Days

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Property Description

Island Pineapple

404 80th Street

Holmes Beach, FL 34217


Tropical landscaping, modern updated interior spaces, and room for the whole family are waiting for you at Island Pineapple. This large four-bedroom, four-bathroom private home can comfortably accommodate up to eight guests. With a prime location in Holmes Beach, you will find yourself close to local favorite restaurants and shopping. The newly updated pool with multiple water features and ambient lighting is sure to be your favorite feature of the home. The expansive pool deck is viewable throughout the home’s main living spaces, including a wraparound balcony overlooking the pool.

You’ll find Island Pineapple’s main living space on the home’s second floor. With an open floor plan and vaulted ceilings, the home welcomes natural lighting through its many oversized windows. The living area was designed with vacation in mind and provides the perfect place for relaxing together after a day spent enjoying your private pool! The modern kitchen has granite countertops, custom white cabinetry, and a full suite of stainless steel appliances. The kitchen comes fully equipped with cookware and dishware for preparing your favorite meals. With a large breakfast bar and open dining area, you’ll find space for everyone to share a meal together.

All four bedrooms are located on the second floor. The oversized primary bedroom enjoys views of the pool deck. With comfortable furnishings, a flat-screen TV, and private en-suite bathroom with new modern shower, you’ll easily find your home away from home here. The remaining three bedrooms include charming beach décor and flat-screen TVs as well. The massive balcony overlooking the pool deck is accessible from multiple places throughout the home’s second floor. The balcony features one of the two outdoor dining spaces.

Island Pineapple’s first-floor spaces feature the amenities that are going to take your vacation to the next level. The private game room has everything you need to entertain the kids and kids at heart in your party! Here you’ll find a pool table, ping pong table, and card table, along with a wall-mounted TV with cozy seating. The outdoor spaces at Island Pineapple rival the indoor spaces. The outdoor kitchenette and private gas grill will serve up lasting memories all vacation long. You’ll also enjoy multiple outdoor seating options and the home’s second outdoor dining space on the first floor.

The private pool will steal the show of your vacation! With three waterfall features and ambient lighting, the pool can be enjoyed throughout the day and into the evening! A bonus highlight of Island Pineapple is the whole home air purification system designed to disinfect the air by neutralizing airborne pathogens including bacteria and viruses. Book your vacation to Island Pineapple by Anna Maria Vacations today!


  • 5 Minute Walk to the Beach

  • Screened-In Pool with Three Waterfalls and Ambient Lighting

  • Whole House Air Purification System

  • Covered Lanai with Outdoor Seating

  • Outdoor Kitchenette, Private Gas Grill, Outdoor TV

  • Great Location Near Shopping and Dining

  • Large Balcony Overlooking Pool Deck

  • Pack N Play, Highchair and Booster Seat Provided

  • Off street parking for boat trailer

  • On Our Professional Linen Program

  • Poolside Air Hockey Table

  • Game Room with Ping Pong and Pool Table

  • Primary Bedroom, Second Floor: King

  • Second Bedroom, Second Floor: King

  • Third Bedroom, Second Floor: Queen

  • Fourth Bedroom, Second Floor: Two Twin/Twin Bunks

  • Primary En-Suite, Second Floor: Soaking Tub, Walk-In Shower

  • Second Bathroom, Second Floor, Hallway: Tub/Shower Combination

  • Third Bathroom, Second Floor, Hallway: Walk-In Shower

  • Fourth Bathroom, En-Suite, Second Floor: Walk-In Shower

Island Pineapple participates in our Professional Linen Service Program which provides the guest with freshly laundered, high-quality linens 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.

~103 Island Pineapple is a perfect rental for those who love to spend time at the pool and the beach. The ground floor of the home is likely where you’ll spend a lot of your vacation. There is a covered patio area with a grill, full-sized outdoor dining set, an outdoor kitchenette, poolside air hockey table, and plenty of lounge chairs. The large private screened-in heated pool features 3 waterfalls, ambient lighting, and in-water seating for guests.

In addition to these incredible amenities, Island Pineapple is a short walk to Holmes Beach, allowing guests easy access to white sugar sand and the salty Gulf waters. It’s also near lots of local shops and eateries and close to the famous Anna Maria City Pier and Rod and Reel Pier. The five-star reviews say it all – book this rental fast because it’s a gem in the Holmes Beach community perfect for spending your memorable Florida vacation!

Please note: 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. This property requires a 7-night minimum stay as set forth by Holmes Beach’s Land Development Code. Occupancy may not exceed 8.


Activities and Special Interests

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

» Beach
» Biking
» Boating
» Canoeing
» Fishing
» Deep Sea Fishing
» Golfing
» Horseback Riding
» Hunting
» State National Parks
» Nightclub and Disco
» Ocean
» Sailing
» Scuba Diving
» Surfing
» Fly Fishing
» Wind Surfing
» Hiking
» Family Vacations
» Kayaking

Other Activities and Interests:
Dining, Shopping, Yoga Sessions, Paddle Boarding, Parasailing, Rent a Jetski or Waverunner, Sightseeing, Visit the Marine Lab and Aquarium, Local Farmers Market, Marie Selby Botanical Gardens, Downtown Venice Art Classic, Enjoy Main Street Live, Beach Bistro’s St. Patrick’s Day Parade, Beach’N Food Truck and Music Festival, Spring Fest, Experience Blue, Brews, & BBQs in late April, Stunning Beaches, Kayak Tour, Nature Hike, Rent a Boat to Go Fishing, Incredible Wildlife, Head to the Best Bars in Florida, Unique Boutiques, Easy and Fun Day Trips, Golf Cart Rentals on Anna Maria Island, Visit the Anna Maria Island Historical Museum, South Florida Museum, Bishop Museum of Science and Nature, Florida Maritime Museum

Featured Amenities

» Air Conditioning
» Cable/Dish TV
» Dishwasher
» Grill
» Internet Access
» Pool (Private)
» Washer/Dryer

Property Features

» Balcony
» Ceiling Fan(s)
» Coffee Maker
» Deck/Patio/Porch
» Dishes/Utensils
» Filtered Water
» Freezer
» Full Kitchen
» Ice Maker
» Microwave
» Oven
» Parking
» Refrigerator
» Towels/Linens


» Game Room
» Pool Table

Other Property Amenities

Television, Bikes, Deck / Patio, Close to Gulf, Deck Chairs, Ping Pong


Paradise 2020-11-10

By: Crystal Popp Trip Date: 2020-09-19
We’ve traveled a lot to Florida over the years but this place by far was the most beautiful place we’ve ever stayed! When you walk in it is huge! It takes your breath away! It’s decorated beautifully. The master bedroom is amazing and elegant! We didn’t need anything, the house has everything you need for traveling to the beach, cooking in, etc! The game room was fantastic for our kids and don’t even get me started on the pool! The pool was amazing and was screened in so we didn’t have to worry about getting burned yet could still enjoy the beautiful weather! We had lunch outside by the pool most days! Quiet community and close to the beach. We enjoyed the short walk to the beach looking at all the other houses and palm trees along the way. People are so friendly on Anna Maria Island. Will definitely be back and wouldn’t stay anywhere else!

Wonderful 2020-10-16

By: Karen H. Trip Date: 2020-09-12
We had an amazing time at this house. It is spacious and you cannot ask for a better pool area. Unfortunately we had a tropical storm and flooding for 3 days of our stay but the pool, outside TV and all the entertainment choices at this house the rain didn't phase us at all. The few times I reached out to the rental company they were responsive and helpful. We plan to rent this house again! -- Karen, thanks for the kind words about Island Pineapple and Anna Maria Vacations! We are so sorry that the weather wasn't cooperative to your beach getaway, but so glad that the home provided you some options for indoor, rainy days! We look forward to having you back on AMI very soon!

Big and beautiful 2020-07-25

By: Melody Metzger Trip Date: 2020-07-11
We had an amazing time visiting the Island Pineapple house! When you walk in, you are blown away by the size of the house and the beautiful decor! The rooms were great sizes and we (3 families) felt very comfortable with the amount of space we all had! The game room was a nice bonus which included legos, a tv with systems, pool and ping pong table, and games. The pool was refreshing and clean. Laying by the poolside was a great way to relax after the short walk by from the beach. We will definitely be back. -- Thank you for the review of your recent stay at Island Pineapple! We are so happy to hear that you enjoyed your time on AMI and laying poolside was a great way to relax. We look forward to welcoming you back again to the Island!

Loved this large open home and pool! 2020-03-08

By: James Roadman Trip Date: 2019-03-02
We had an amazing time at this beautiful home! It is such a big home to spread out in, which was great because we have such a big family. The pool is so big, we could barely get the kids to get out of it. ? we loved all the living area being on one level so we weren’t up and down stairs to get to the bedrooms. The beach and weather were truly amazing, can’t wait to come back! -- Thank you so much for the 5 star review! We are so happy that you had an amazing time at Island Pineapple and that there was room for the whole family! We are glad that you had good weather for the duration of your stay and look forward to welcoming you back to AMI soon!

Perfect big family rental 2019-03-06

By: Christy Raulerson Trip Date: 2019-02-02
My sister and I and our 2 big families stayed here for 3 weeks. We loved it! SO MUCH room and all on one floor. No multiple flights of tiles stairs that we’ve experienced at other rentals. We all had large rooms with our own bathrooms, the kitchen is great, a large relaxing living room, plenty of parking, and an Awesome pool. The pool was so big the kids could kayak in it and they played on the air hockey and ping pong tables for hours. We loved having lunch in the outdoor dining/kitchen area. The house was well stocked with games, movies, and beach supplies. The kitchen was well stocked as well. The master bedroom was Beautiful and we loved the huge soaker tub! It was also a really quiet street. A short walk to the beach...We took White Ave (one street over) out to the beach everyday because they have a shower and a bathroom at that beach entrance. We enjoyed our time here very much! Happy memories made at The Island Pineapple! ❤️?❤️ -- Christy, thank you for the 5 star review of Island Pineapple! We are so glad you enjoyed this property and it's amenities including the large pool, air hockey and ping pong table, and short walk to White Ave. We thank you for staying with us and hope to have you back soon for more happy memories!

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