Pineapple Key: Anna Maria Island Vacation Home for Rent Close to the Beach in Holmes Beach Florida with Pool and 4 Bedrooms

Pineapple Key: Anna Maria Island Vacation Home for Rent Close to the Beach in Holmes Beach Florida with Pool and 4 Bedrooms

Holmes Beach family vacation home 4 bedrooms with pool and close to the beach on Anna Maria Island : Pineapple Key

Vacation Home in Holmes Beach Florida

4505 Gulf Dr
Bedrooms: 4 Bedrooms • Sleeps 8
Bed Arrangements: 2 Twin over Twin Bunk Bed - 1 Queen Bed - 2 King Bed - 1 Sleeper Sofa QUEEN
Bathrooms: 2 Full Bathrooms
Location Setting: Waterfront - Nearby
Beach Access: Near a Beach
Air Conditioning: Yes
Pool: Pool (Private)
Hot Tub: Hot Tub (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 $600 per night
  • Weekly Rates from $1,400 to $5,600 per week
  • Minimum Stay: 7 Days

Already Booked

Property Description

Pineapple Key

4505 Gulf Drive

Holmes Beach, Fl 34217


Pineapple Key is a completely renovated single family home with 4 bedrooms, 2 bathrooms and a private heated pool with spa! Located just 2 blocks away from the pristine white sandy beaches of the Gulf of Mexico-you are just a short walk away from experiencing some of the best beaches of the world!

Equipped with 2 living areas and upgraded furnishings, appliances and fantastic amenities-that are sure to be a hit with everyone in your group! There are 6 TV's for your enjoyment-including 4 Smart TV's-a pool table, Wii gaming station, board games, beach chairs and pool toys.

Conveniently located only 2 houses away from a Trolley stop, a free Island service, which runs from the North end of the Island to the South end from early mornings through to late evenings. You won't need to turn on your car all week-simply catch the Trolley to all of the fantastic amenities that the Island has to offer. Explore local shops, boutiques or go on the hunt for the best grouper sandwich and seafood at one of the many great restaurants.

After a day of scouting out the beaches and local amenities, return back to your own personal slice of bliss! Jump right in to the private heated pool or relax and let all of your worries slip away while you enjoy the spa. Grill up your catch of the day on the charcoal and gas grill combination or take advantage of the fully stocked gourmet kitchen to prepare a delicious homemade meal!

Offering something for everyone to enjoy-Pineapple Key will be a hit with your whole family!

Completely renovated single family home
4 bedrooms and 2 bathrooms 2 Kings, 1 Queen, 2 Sets of bunks, 1 Queen sleeper sofa 2 Blocks from the Gulf beaches Private heated pool with spa-covered living area by the pool Pool table, Wii gaming system, board games, 6 TV's and 3 DVD players Only 2 houses away from freeTrolley stop New Travertine floors, trims, molding, granite counters and more 2 Living areas-front and rear porches


Pineapple Key has 4 bedrooms and 2 bathrooms. This fantastic and newly remodeled home offers 2 King sized beds, 1 Queen, 2 sets of bunk beds and 1 Queen sized sleeper sofa. This home can comfortably accommodate a group of 8


There are 2 bathrooms. The first bathroom offers a stand in shower, while the second bathroom features a tub with glass sliding doors.


Pineapple Key features a great backyard with a private heated pool and spa. Enjoy the two separate sitting areas, fantastic for enjoying an outdoor meal or your favorite ice cold beverage before hopping into the pool! Challenge a friendly game of pool or take advantage of the BBQ grill to make up your catch of the day or explore some of the fantastic eateries the Island is known for-its great location puts you in the middle of it all!

Take the free Island trolley, take a stroll or rent bikes to explore all of the wonderful amenities the Island has to offer!

There are 2 covered parking spots available plus an additional 6 uncovered spots.

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
» Spa
» 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
» Hot Tub (Private)
» Internet Access
» Pool (Private)
» Washer/Dryer

Property Features

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


» Pool Table

Other Property Amenities

Television, Covered Parking, Deck / Patio, Spa, Deck Chairs, Ping Pong


Great House for Family Vacation! 2020-11-16

By: Amber J. Trip Date: 2020-10-10
Overall, the location and house was everything that was described. They have 4-5 beach chairs, umbrella, cooler and several beach towels. Very well stocked. I will stay again, just under different circumstances. This statement is only to help another family or group of friends, like we had during our trip. This is in a residential neighborhood (as described). If you have a rowdy group that likes to hangout outside, listen to music and enjoy the outdoors after 10p, this is not the spot. We had neighbors at 5p asking us to turn the music down. There is a noise ordinance at 10p that is outlined in your agreement. If you’re coming with a younger group, this may not be your spot. Other than that, it was in a great location with easy access to beach and a beautiful house! -- Amber, we are so happy that you liked Pineapple Key. Anna Maria is definitely a more laid back vibe than other areas of Florida. Almost all of our rentals are located in primarily residential areas and the quiet, "old Florida" feel of the island is what keeps a lot of our guests coming back year after year. I do agree that this is not the ideal place for a party crowd to come for a vacation ~ but that is by design. We hope that this wasn't too much of an inconvenience to you and that you enjoyed your time on our quiet little piece of paradise!

Perfect family getaway! 2020-07-28

By: Dawn Trip Date: 2020-06-06
Have to admit this was a backup plan. With the pandemic we had to make other celebration plans for my 50th birthday. So my family surprised me by renting this house for the week. It could not have been anymore perfect! It was such a great location and plenty of space for the entire family to relax and have fun! All pool and beach amenities were provided which was perfect since we didn't have much time to plan. And the place was spotless clean! I clean for a living so I'm very picky. No complaints here! -- Thank you so much Dawn for taking the time to leave Anna Maria Vacations a 5 star review! We are so happy to hear that you and your family enjoyed your 50th birthday celebration at Pineapple Key! We are glad there was plenty of space for the the entire family to relax and have fun! We hope to welcome you back to the Island as our guests in the future.

Wonderful week 2020-07-16

By: Diane Hoffstedder Trip Date: 2020-06-06
We had a wonderful week spent with family. The pictures don’t do this place justice! It’s such a beautiful and fun space. Our kids never ran out of things to do. This is a perfect space for families to gather - everything you could possibly need or want is here - from pool/beach gear, easy walk to beach, cooking utensils and entertainment/games. My kids found the Wii half way through the week and even the adults joined in! Property management was easy to work with and accommodating. My only suggestion is that the bath towels need to be replaced/freshened up. I would highly recommend this house. -- THANK YOU so much for the five-star review of Pineapple Key! We are so happy that you and your family found the house to be such a great fit for you all! We will be sure to pass along your suggestion regarding the bath towels to the owners of the home. We very much appreciate your feedback on your stay!

Close Enough to Beach 2019-12-30

By: Kelly Parcher Trip Date: 2019-12-20
Unit was clean and fully stocked. Good distance to beach (block away). Right on a busy street, if you have little kids that might be stressful. It was perfect for us! Would definitely stay here again. Perfect for our family (4 teenagers). -- Thank you for the kind review, Kelly! We are so happy to hear that you enjoyed the convenient location to the beach and that Pineapple Key was perfect for your family! We are glad that you enjoyed your stay on AMI and we look forward to welcoming you back soon!

Awesome location and perfect for families! 2019-11-05

By: Chelsea Quick Trip Date: 2019-10-19
This house had all we needed for our kids and parents. Perfect for a family get away with great indoor and outdoor space. Would definitely go back! -- Thank you for the 5 star review Chelsea! We are happy to hear that you and your family had the perfect getaway at Pineapple Key! We look forward to welcoming you back soon!

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