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
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 $250 to $650 per night
  • Weekly Rates from $1,750 to $4,550 per week
  • Minimum Stay: 7 Days

Already Booked

Property Description

Island Pineapple

404 80th Street

Holmes Beach, FL 34217


Island Pineapple is a gorgeous newly renovated 4 bedroom and 4 bathroom home that features a stunning backyard oasis perfect for a great getaway. The pool area was truly designed with entertainment in mind. Sit back and relax under the covered balconies next to one of the island’s largest privately owned screened-in heated pool. There are three covered open-air lounging areas surrounding the pool for relaxing in the shade! Enjoy grilling a family meal outdoors or gather round to watch the game on the large flat screen TV-poolside. Outdoor enjoyment simply does not get better than this! In addition, a separate large air-conditioned playroom downstairs also provides additional space where everyone can enjoy playing games, compete in ping-pong or pool, and enjoy some video games on the big 58” TV. And, with the beach being only a couple of blocks away, beach towels, beach chairs, umbrella are provided for your use along with wagons to help you enjoy your time at the beach. Professionally decorated and recently renovated, the interior of this amazing home is just as grand. The open concept kitchen, dining and living areas allow everyone to spend some quality time together while still offering enough space for privacy when you want to enjoy some quiet moments. There are generous quantities of dining and cooking utensils, as well as ample linens and towels. Have small children – no need to rent equipment. For your convenience, a highchair, toddler seat and pack-n-play are provided on-site. No small detail was overlooked for your luxurious Anna Maria Island getaway.
Unwind in paradise and take advantage of the incredible location, large open layout and wonderful amenities when you choose to vacation at Island Pineapple. Call our reservations
team today to start planning your getaway!


  • 2,750 sq feet with open floor plan

  • Custom 4 bedroom and 4 bathroom home

  • Only 2 blocks from the Gulf beaches

  • Private screen-in heated pool

  • Covered lanai with plenty of outdoor seating

  • Great central location near shops and restaurants

  • Large balcony with perfect outdoor dining area

  • Professionally decorated

  • Gourmet kitchen

  • Bikes

This beautiful home features 4 bedrooms and 4 bathrooms--with 2 kings, 1 queen and 2 sets of bunk beds.

Relax and unwind in your own backyard oasis at Island Pineapple. Enjoy the large private heated pool or play a fun game of pool-side air hockey. The covered and screened lanai offers plenty of outdoor seating and makes for a great gathering place to enjoy a meal grilled on the BBQ provided for your convenience.

Our pools are heated during the months of November through April at no additional charge to our guests. We do not heat the pools during the warmer months of May through October. If you are renting between November and April and you would like to have your pool heated, we kindly ask that you please contact AMV at least 10 days prior to your arrival so that it ensures us ample time to fulfill your request. Pools are heated to a temperature of 82 degrees. However, please be aware that even in Southwest Florida we do occasionally get cold spells that can send the temperatures down into the 30's for a few nights in a row. This will cause the pool water temperature to draw down to in the 70's and a pool pump will automatically shut down if the outside temperature gets too cold. When the weather gets warmer and the pumps are able to re-engage, please be mindful that re-heating of the pool back to 82 degrees may take several days depending on the severity of the cold spell. Ultimately, these situations are beyond our control. Other issues such as severe weather conditions, equipment malfunction, temporary loss of use of equipment or amenities due to maintenance purposes or other items do happen from time to time. All of our pools and pool equipment are closely monitored by the pool companies. For your safety, we kindly ask that the controls not be tampered with -most of the systems are locked for this reason. Due to the island's strict 10pm noise ordinance, the pool heaters will not run overnight. Please remember, outdoor spas are not hot tubs. Please be aware that AMV does not issue refunds based on acts of god. However, please know that in the rare event of pool equipment malfunction during your stay, AMV will do everything in our power to expedite repairs as quickly as possible as we certainly want you to enjoy your heated pool and Florida sunshine to the fullest extent possible!

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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