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Pineapple Key
- 4 bedrooms and 2 bathrooms in Holmes Beach, FL

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At A Glance

  • 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

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, pool toys and more!

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!

Bedrooms & Bathrooms


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.

** If 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. We do offer pool heat as needed as a courtesy to our guests at no additional charge. All of our pools and pool equipment are closely monitored by the pool company 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 (some properties have a spa, some have a hot tub). Generally speaking, our winter months are considered from November through April. During these months we do our best to ensure that the pools are heated to a temperature of 82 degrees. However, please be aware that even in Central 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. The pump will then kick back on in the morning and begin re-heating of the pool back to 82, which 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 for time to time. Please be aware that AMV cannot issue refunds during your stay 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! Anna Maria Vacations thanks you in advance for your understanding on this issue.

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The house is great – Anna Marie Vacations – not so much

By: Trip Date: 03/30/2019

The house was great overall. We did miss having dressers in the bedrooms but was able to make do. The downstairs area was awesome and all that we had hoped it would be. Unfortunately, there were three things wrong with the house when we arrived. One, the closet door would not open and close. Two, the screen on the back porch slider was ripped. Three, the hot tub would not work. Anna Marie Vacations sent a maintenance person out right away which was awesome. Unfortunately, he was only able to fix the closet door. He said he would come back the next day to fix the screen which he did not. He said he would call the pool company to come fix the hot tub and they did not. When the pool person showed up on Friday he did not know anything about the pool not working and said it wouldn’t work as it was off line. After this experience I would hesitate to rent anything that is managed by Anna Marie Vacations.

Thank you for taking the time to write a review.  We appreciate the feedback on your experience with us and I’m sorry that you are disappointed in our service during your stay.  I know that we have spoken about this at length and unfortunately we are at a bit of a loss as our head Service Technician and the owner of the pool company that services this home both came over and found the spa to be working properly.  We also have the instructions for how to operate the equipment posted at the home in case there is any confusion on the part of our guests as to how it operates. We are happy that your overall impression of the house was great.  It really is a wonderful place to spend your time on the Island and after our last conversation, it seems as if we hopefully will be welcoming you back!

Great House

By: Trip Date: 12/31/2018

This home was perfect for our family, plenty of room with lots of seating. Close to the beach. Spa and pool were great for all of us. Lots of sand toys, beach chairs and cart to take it all to the beach. Full size washer and dryer was a plus, as was the fridge downstairs by the pool.
We would recommend this home to anyone. Doesn’t look like much from the outside but super nice on the inside.

Hi Kris,
Thank you for the great feedback on Pineapple Key! We’re glad the whole family enjoyed the location and pool area. We’re happy to hear the beach amenities and washer/dryer came in handy as well! We appreciate the kind words and hope to see again soon!

Great rental

By: Trip Date: 12/31/2018

This was a perfect home for our family vacation, close to the beach, heated pool, great spa. Plenty of beach towels, beach toys, beach chairs and a cart to take it all with you. Would definitely recommend this property.

Hi Kris,
Thank you for the awesome review of Pineapple Key! We are so glad you enjoyed your stay, as well as, the additional amenities and location. We appreciate the kind words and hope to see you again next year!


By: Trip Date: Aug 4th - Aug 11th.

Our whole family stayed ther for our 25th Anniversary & we renued our vows on the beach. We all were very surprised how big it was & the way it was set up, loved how each area had its own lil theme. We couldn’t get over all the beach towels & beach accessories ther were toys, chairs, umbrella, bikes, etc. We never ran out!! & alot of towels 4 showers also. The beds were all so very comphy & cozy we all slept great never a complaint bout the beds & big fat cozy pillows! big plus ther!! We will definitely b back ther & probly stay here again! The pool & spa were a big hit expecially for my 7 yr old Granddaughter couldn’t keep her out! 🙂 This us a very beautiful big property & I highly recommend it!! 🙂 We ❤️’D it!! Thanks 4 the great stay, Gomez Family! 🙂

Hi Jo Ann,
Thank you for telling us about your stay – we’re so happy you enjoyed Pineapple Key! We’re glad the beach amenities were plentiful for you and that the beds were cozy and comfortable. Very happy to hear that your granddaughter had fun in the pool and spa! We greatly appreciate the kind words and we’d love to have you back again!

coming down in August this year!!

By: Trip Date: 08/04/2018

We was just reading some of the reviews & it sounds & looks so beautiful we can’t wait to be there!! Were just hoping that you guys have fixed the pillow situation in the rooms & have added a shelf or 2 to put your belongings on especially when staying 4 a whole week its hard living out of a suitcase for that amount of time. & maybe update the pots & pans. Im sure we will have a great time no matter what, but good pillows are best for a good nites sleep for a fantastic next day. 🙂 WE just can’t wait to be there & enjoy this beautiful place!!! Thanks so much hope to hear from you soon, Jo Ann Gomez 🙂

Hi Jo Ann,
We are so glad to hear that you’re excited for your stay, we’re excited to have you! We hope you enjoy your time at Pineapple Key and experience all that Anna Maria Island has to offer. Should you have any maintenance or housekeeping issues for any reason, feel free to call our office so we can get it taken care of for you! Thank you for the kind words and we look forward to having you!

Fell in love at first sight!

By: Trip Date: 03/03/2018

Loved, loved, loved this place! The location is fantastic (although it is a tad tricky getting out of the driveway and back into traffic) but just a block or two to the beach, trolley stop two houses down and close to everything! The entertainment area below is superb! Fun tiki bar, pool table, comfortable seating, large dining table! The pool and spa are fantastic! The only negative was the pool was cold (the weather was mainly in the 60s when we were there) and we were not aware that you can only heat either the pool area or the spa area so we mainly lived in the spa to stay warm and jumped into the pool when we got too warm! It worked but I would have loved to have been there when the weather was warmer so hence the pool would be as well. There is also a washer/dryer and refrigerator in a room downstairs. The amount of pool tools, beach chairs, umbrella, etc. was a fantastic surprise. The house also comes with many large beach towels to use! The actual house is set up so smart with a living room area on each end and a kitchen/dining area in the middle – all open concept. The other side of the house is divided into bedroom/bathroom/bedroom and again repeat on the other side so it’s almost like having two separate areas and just sharing the kitchen/dining area. Both ends of the house have decks as well and staircases to below. There is a gas grill we put to good use. The furniture is comfortable. The bathroom has motion nightlights – nice touch! The only things I thought that could be improved were the pillows on our king bed were worn out and needed to be replaced. There are no dressers in the rooms so it would have been nice to have a shelf or something in the closet for clothes (some of the closets did have various things but ours did not), the plastic wine glasses are no longer round (victims of the dishwasher I assume – LOL!) and some of the pans in the kitchen have seen better days but overall – fantastic! Nicely decorated – great colors – lots of serving trays, bowls, utensils, dishes, etc. The kids thought the downstairs could have used a few more lights so you can see when grilling at night and/or just hanging out around the pool in the evening but it was not a deal breaker. We all loved it and highly recommend this place.

Hi Kris,
Thank you for telling us about your stay – we greatly appreciate it! We are so happy to hear that you enjoyed your time at Pineapple Key and the location of it. We’re sorry to hear about the cooler weather during your stay but glad to hear that you still enjoyed the pool and the entertainment area with the tiki bar and pool table! It’s great to hear that the layout of the house was a good fit for all of you and we appreciate the kind words about the décor. We’re thrilled to hear that you all enjoyed it and we hope to hear back from you soon for your next stay on Anna Maria Island!

Perfectly Lovely

By: Trip Date: 07/08/2017

From beginning to end of our week, this place was wonderful! Beach access is close, and even with paddle boards and skim boards, the trek was easy. The house also included lots of fun toys for the beach and pool. As a previous reviewer noted, the street is somewhat busy, but people stopped courteously every time we needed to cross, and we were back and forth from the beach a lot. The fact that the pool is partially shaded was an added bonus for our pool lovers.
In addition, when I sent a note to the property managers about a coffee pot that had been broken before we arrived, I told them that it wasn’t a big deal and that we could manage with the other coffee maker. They still showed up the same day with a replacement!
Anna Maria is what beach towns should look like… easy going and family friendly…and of course, you can’t beat the sunsets!

Hello Curt,
Thank you so much for letting us know about your stay at Pineapple Key.  We are thrilled to hear that you enjoyed the amenities the home provided and that you were happy with our service! Please let us know when you are ready to visit our beautiful island again.  We would love to have you stay with us for your future Anna Maria Island vacation needs!

Good house for family with older kids

By: Trip Date: 03/04/2017

The home was well-appointed, but a few too many knick-knacks that interfered with the placement and storage of a normal family’s vacation “stuff.” This home sits right on Gulf Ave., a very busy (noisy) thoroughfare, and so the front deck is useless unless you like looking at traffic. The sliding glass door to this front deck has no privacy shade or drapes which is disconcerting on such a busy street with the harsh street lights glaring in. The back deck is quiet and has a table and chairs, but no umbrella to shade you from the strong Florida sun. There is no safety lock on the front door to keep babies in, the 18 month old kept flinging the door open. Scary! The beds are soft pillow topped and only two bedrooms have dressers to store clothes.(one closet had no pole to hang clothes and another had one door off the track). The rental agency left a note for our arrival that there were some known issues with the house that they were aware of and would correct, but they never came while we were there. My guess is these were the issues and they will possibly be fixed soon.
The real treat about this house is the fun lower level which has a nice private pool with spa waterfall, living space, grill, table and chairs for 8, pool table, tiki bar and an enclosed laundry room which also houses another refrig/freezer, and beach and pool accessories (toys, beach towels, some chairs, umbrellas). This lower level is all open to the elements and landscaped very nicely, except the cement decking needs to be repainted.
You are close to the stop for the trolley, which is great, but we had to hold children’s hands tight as soon as we came around to the front of the house because of the proximity of the street, and to wait for traffic to stop so we could cross to get to the beach only 2 short blocks away. Overall my family adapted to the location and had a very nice time, but next year with our small grandchildren, we will look for a home that is off the highway.

Hello Mary Kate,

Thank you so much for letting us know bout your stay with us at Pineapple Key.  Your feedback is important to us as it helps us better assist our future guests.  We are sorry that the location was not as you expected it to be.  Though the deck does face Gulf Drive, the main road on the island, the speed limit is 25 mph and we have not had any negative guest experiences due to noise.  Your review has been forwarded to the appropriate departments for further evaluation.  Please note that our Service Department is available 7 days week to address any issues that may come up during your stay.  We have over 200 homes in our rental pool and are confident that we can find the perfect vacation home where you don’t have to cross the street to get get to the beach for you and your family for your next years Anna Maria Island stay.