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Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life

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Pool
Pool
Pool
Pool
Pool

Reviews

9.0 out of 10
Wonderful
4 bedrooms4+ bathroomsSleeps 8

Popular amenities

  • Private pool
  • Garage parking available
  • Pet-friendly
  • Kitchen
  • Washer
  • Air conditioning

Explore the area

View in a map
Holmes Beach, FL
  • Place, Palmetto Avenue Beach
    ‪6 min walk‬
  • Place, Bradenton Beach
    ‪6 min walk‬
  • Place, Bean Point Beach
    ‪4 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪31 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bunk Bedroom with 4 Twin Beds, TV, 2nd Floor

2 Twin Bunk Beds

King Bedroom 1, TV, Ensuite, 2nd Floor

1 King Bed

King Bedroom 2, TV, Ensuite, 2nd Floor

1 King Bed

King Bedroom, TV, 2nd Floor

1 King Bed

4 bathrooms, 1 half bathroom

Guest Bathroom 1, 2nd Floor

Toilet · Shower only

Guest Bathroom 2, 2nd Floor

Bathtub or shower · Toilet

Half Bathroom 5

Toilet · Shower only

King Bathroom 1, Ensuite, Dual Sinks, 2nd Floor

Bathtub · Toilet · Shower only

King Bathroom 2, Ensuite, 2nd Floor

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Garden
Dining area

About this property

Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life

Island Pineapple by Anna Maria Life Vacation Rentals
404 80th Street, Holmes Beach, FL 34217

What You'll Love About This Home:
Location! 5 Minute Walk to the Beach!
4 Bedrooms / 4 Bathrooms
3 King Beds / 2 Sets of Twin over Twin Bunkbeds
Private, Heated, Screened Pool with Waterfalls & Ambient Lighting
Wrap Around Balcony Overlooking Pool
Covered Lanai with Outdoor Seating
Outdoor Kitchen with Gas Grill & TV
Whole Home Air Purification System
Professional Linen Service and Washer & Dryer
Complimentary WIFI
Beach Towels, Chairs, Wagon
Parking for 5 Cars

Details:
Island Pineapple will delight the beach vacation in you! Located a quick, five minute walk to the sugar sand beaches of Anna Maria, our home is made for vacation!

With the main living space on the second floor and many oversized windows, the home is bathed in natural light. Have the chef in your family create your favorite meal in the modern kitchen. The large breakfast bar and open dining area provide ample space for everyone to dine together. Outdoor dining is also an option on the covered lanai with patio seating.

The bedrooms are all located on the second level and have access to the wrap around balcony overlooking the pool. The master has a king sized bed, en-suite bathroom and views of the pool deck. Two of the guest rooms have king beds with the third guest room with two sets of twin over twin bunkbeds. Two of the king guest rooms have an ensuite bathroom. Each of the bedrooms features a TV. Guests will enjoy crisp linens and plush towels from our professional linen company. Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.

The main level of Island Pineapple is for fun! A kitchenette with BBQ grill and outdoor patio dining set make poolside meals easy! The large private screened-in heated pool features 3 waterfalls, ambient lighting, and in-pool seating.

After a day soaking up the sun at the beach, the sparkling heated pool welcomes you home with three waterfalls, ambient lighting, and in-pool seating, all under the comforts of a pool screen.

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.

Island Pineapple is easy walking distance to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. Island Pineapple is the perfect location for your next beach vacation.

This home is dog friendly with a pet fee of $150 plus tax per dog. If you have added a pet to your reservation, the fee including tax ($168) has been included in your total.

All Bedrooms are on the 2nd Floor (main living level)
Master Bedroom: King Bed with Ensuite Bathroom
Second Bedroom: King Bed with Ensuite Bathroom
Third Bedroom: King Bed
Fourth Bedroom: Two Sets of Twin over twin Bunkbeds

Please note:
Amenities are subject to change.

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. The minimum requirement for this home is no less than seven nights. The maximum occupancy is eight.

VRC19-000013

Golf Cart DEAL ALERT!!!
Reserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.
FUN way to explore the island for the entire family.
Mention Anna Maria Life Vacation Rentals and receive this VIP deal!
www.FunAndMoreRentals.com
941-462-2719

IMPORTANT INFORMATION:

Your booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.

** Your signed rental agreement must be returned in order to receive your check-in details.

VRBO BOOKINGS

Anna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.

Your final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance.

The instructions for making your final payment will be included in your final payment reminder.

Please review the cancellation policy prior to booking.

GOOGLE VACATION RENTAL BOOKINGS

Your payment is due in full at the time of booking and the final balance information above does not apply to your reservation.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock

About the neighborhood

Holmes Beach

Located in Holmes Beach, this vacation home is near theme parks and near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Looking to enjoy an event or a game while in town? See what's happening at LECOM Park or IMG Bollettieri Tennis Academy. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
View more Vacation Homes in Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Palmetto Avenue Beach - 6 min walk - 0.6 km
  • Bradenton Beach - 6 min walk - 0.6 km
  • Island Players - 18 min walk - 1.6 km
  • Anna Maria Island Museum and Historical Park - 3 min drive - 2.1 km
  • Bean Point Beach - 4 min drive - 2.7 km

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 31 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬6 min drive
  • ‪The Ugly Grouper - ‬3 min drive
  • ‪The Sandbar Restaurant - ‬17 min walk
  • ‪The Waterfront Restaurant - ‬4 min drive
  • ‪Ginny's & Jane E's - ‬14 min walk

Frequently asked questions

Does Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life?

As of May 6, 2026, prices found for a 1-night stay for 2 adults at Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life on Jul 18, 2026 start from $744, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life?

Check-in begins at 4:00 PM.

What time is check-out at Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life?

Check-out is at 10:00 AM.

Where is Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life located?

Situated by the sea, this vacation home is within a 10-minute walk of Palmetto Avenue Beach and Bradenton Beach. Island Players and Anna Maria Island Museum and Historical Park are also within 1 mi (2 km).

Reviews

9.0

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 16 out of 23 reviews
Rating 8 - Good. 3 out of 23 reviews
Rating 6 - Okay. 3 out of 23 reviews
Rating 4 - Poor. 1 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.4/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jess B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved this house! The listing doesn't even do it justice!! We had the best time! The pool area is phenomenal, with lots of seating! The beds were all comfortable and the kitchen had everything we neede to maje meals. We cant wait to come back!
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Katherine R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay

Loved our time at the home and in Anna Maria!
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Jeffrey S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place

Property was nice and good location
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Jordan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay

Impression was great. The outdoor hockey table is pretty much unusable but we loved the pool, closeness to the beach, and the size of the property. Would stay here again
Stayed 7 nights in Feb 2024
Verified

10/10 Excellent

Barbara C.

Liked: Cleanliness, check-in, location, listing accuracy

Family vacation

This property was amazing as it had lots of space. The pool area was incredible and the living space huge. We had 7 adults and it was perfect
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Veronica S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Island Pineapple - Bliss

Beautiful, clean property in a prime location. Would highly recommend.
Stayed 7 nights in Mar 2023
Verified

10/10 Excellent

WPZ22

Liked: Cleanliness, check-in, communication, location, listing accuracy

The Host Services were Excellent

Our stay was delayed due to the Hurricane and the host was able to assist us during the emergency. Great job !!!!
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Michael P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anna Maria Pineapple House

Loved the house and location. Only complaint was the sheets in Master Bedrrom didnt fit properly. My adult daughtet's flew down for a 5 day stay and loved the house. Pool was wondetful
Stayed 14 nights in Jan 2024
From a partner site

10/10 Excellent

Patricia R.

Pineapple House

Lovely home and pool, spacious and well equipped (ping pong, air hockey, pool toys). We had a heating issue with the pool and it was promptly addressed and fixed.
Verified

10/10 Excellent

PAUL C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous.

Upstairs is absolutely gorgeous, with plenty of room and facilities. The pool must be one of the biggest on the island? Certainly the biggest that we've seen! Great for families!! The only downside really is the outside space downstairs around the pool, could do with some sprucing up.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Jamie N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

AMAZING

The house was exactly as pictured, no suprises. We are a family of 6 with children ages 13- 15 months. It was perfect for our family. All the shared areas of the house were very spacious. Kitchen and island were wonderful. The pool was absolutely amazing. It was a very large and warm pool, you could swim in day or night or rain or shine. The house had everything you could need including all kinds of baby items for our 15 month old. We had a wonderul stay. We would recommend this house to anyone!!
Stayed 7 nights in Feb 2021
Verified

8/10 Good

André B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spacious and beautiful house in the best location

The generously sized house in a prime location and within walking distance of the endless white sandy beaches is modernly furnished and has a large pool that can't be seen The master bedroom and accompanying bathroom and walk-in closet are fantastic. In contrast, our friends in the guest room were not completely satisfied with the room size, bathroom and mattresses. Especially the generator, which ran directly in front of the bedroom every morning at 0500 a.m. with great noise for two hours, robbed them of sleep. The alarm system on the only door to the gallery above the pool made going in and out tedious. Otherwise a good house at a fair price in this exclusive location.
Stayed 7 nights in Nov 2022
From a partner site

8/10 Good

Christie A.

Location is perfect! House is wonderful-Just needs attention to a few things.

This was our first time at AMI. We made the most amazing memories and will definitely be returning. This company was truly wonderful to work with AND receptive to suggestions and feedback. We had some issues at check in with the house not being completely cleaned which they remedied. We also made notes of some repairs and updates that need done to the house to make it even more wonderful and they listened and were grateful. It is such a spacious property, the pool is HUGE, and you are truly secluded in your own little oasis when relaxing in the pool. We had a family of 7 and it was perfect amount of space for all of us to not feel like we were on top of each other. The walk to the beach was only 5 min if that and a private access point with very few people. This house truly was a gem and I just would love to see a few upgrades done and some repairs done to make completely perfect. Do not rely on the poolside air hockey table, it doesn't work at all and is just an eye sore really. There is not a pool table as written in the amenities. Another thing to note: getting in and out of the pool is very difficult for elderly people or anyone with a disability/handicap. There is no railing at all and we had to help the older folks in and out. Overall our family loved this house and its location is spot on. Very residential and quiet. Anna Maria Life Vacations went above and beyond listening to our feedback and respected our concerns. This was a wonderful first experience and we will absolutely be back!
Verified

4/10 Poor

Jay P.

Liked: Cleanliness, check-in, communication, location

Beauty is Only Skin Deep

I was disappointed with the property from the beginning. When we arrived we notice that the interior of the house was humid. I attempted to turn on the A/C to decrease the humidity, but because it was 72 in the house the a/c would not go on. Although management sent someone there was no solution. THE HOUSE'S CHIMNEY NEEDED TO BE REPAIR WE KNOW BECAUSE THE REPAIR CREW CAME UNANNOUNCED ON TUESDAY MORNING AND STAYED THE WHOLE DAY HAMMERING ON THE ROOF! The heat was anther story, due the cold weather we needed to heat the house at night, unfortunately one on the bedrooms received little to no heat. By the way the bedroom with a king bed has no closet making us live out of our suit cases. The ice maker doesn't work ,when I brought this to the attention of the management I was told they were aware! Also the hockey table as well as all the ping pong table paddles are also in need of replacement. The provided beach chairs need to be replaced. All have their carrying straps torn, and when our young daughter sat in one of the chairs it broke. The Pluses include a great pool once the heat came on, well equipped kitchen although the dishwasher kept falling away from its position under the counter because it isn't anchored to the counter . All the TV's come with ROKU and the main sitting area allows for a large gathering.
Stayed 14 nights in Dec 2022
Verified

8/10 Good

Virginia G.

Liked: Check-in, communication, location, listing accuracy

May 2021

We have stayed in this beautiful home three times now but this is the first time under new ownership/management. The updated painting is very pretty. The previous bedroom with the daybed has been converted into a bunk bed room which is quite nice. We did have trouble with the WiFi though especially in the back bedroom (not the master). I don’t remember this being a problem before. In general, the home upon entering was very clean but there was candy, candy wrappers, and an opened water bottle left in the master bedroom. There were also a few cockroaches this time. Although encounters with wildlife can’t always be controlled, we did come out to the pool one morning to find a poor exhausted rat swimming in the pool. After rescuing the rat, we contacted management. They in turn contacted the pool company who did clean it but we lost use of the pool for a full day. Rat poop was also discovered to the side of the grill. We also had some issues with water pressure. Work was being done a couple of streets over but it affected our pressure for almost the full two week stay. For the most part, the kitchen was well stocked but some of the pans (especially the skillet pans) were not in great condition and food stuck to them. Some of the small appliances, such as the blender, had not been properly cleaned in a long time. There was dried food stuck to the blender blades. There were no spices other than salt and pepper. Also, we ran into some problems with the washing machine. The first load of clothes that we washed came out with oil/grease stains that ruined several items of clothing. We were never able to get those spots out. Towels/beach towels are provided. Bring plenty of paper products for your stay along with hand soap. With that being said, it is a beautiful home with lots of space. We absolutely love the screened in pool area and the location is very close to the beach. It is only a five minute walk to a gorgeous white sand beach
Stayed 14 nights in May 2021
From a partner site

6/10 Okay

Catherine S.

3 Stars

We had a few problems with door to the upstairs deck door would not lock problem with security alarm because of this, boards on deck were stick up had to call and let them know what was going on they never fixed the door while we were there. Beds were very uncomfortable except for the master bedroom. Very nice home needs some tlc would not rent again very disappointed was to expensive for what you get.
From a partner site

6/10 Okay

Catherine S.

3 Stars

We had a few problems with door to the upstairs deck door would not lock problem with security alarm because of this, boards on deck were stick up had to call and let them know what was going on they never fixed the door while we were there. Beds were very uncomfortable except for the master bedroom. Very nice home needs some tlc would not rent again very disappointed was to expensive for what you get.
From a partner site

10/10 Excellent

Gail R.

Wonderful Rental Experience!

Our family of 6 adults and 2 toddlers had a great time! Plenty of room to spread out, play games, eat, chill, etc. Working with Anna Maria Life Rentals was exceptional. They were quick to answer all questions and went above and beyond. The house is super clean with plenty of floaties, boogie boards, wagon, beach chairs, etc. TV's everywhere! We paid the small extra fee for more pool heat and loved it! They provide just starter essentials, but Publix is within 2 miles. Just a five minute walk to the beautiful beach. We also had a small dog with us and lots of friendly walking areas in the neighborhood. One tip: There's an alarm on the door to the pool balcony that has to be disarmed before opening. Very alarming if you forget! LOL. Thank you AMI Life! Five stars!
From a partner site

6/10 Okay

Jeanne B.

Island pineapple stay

The master bath & bedroom were lovely as well as the kitchen & family room. The whole house could use a good cleaning & touch up painting. The bedroom with the king bed could use a luggage rack or somewhere to put things since it's missing a closet. The bathrooms in the second & third showers are not accommodating for soap, shampoo,etc. The front & two garage side doors could use better doors & locks. I hope this is helpful information, overall we really enjoyed our stay! The outside & pool were fabulous!!!!
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful just beauiful

Property was incredible, amazing, fantastic. It totally surpassed all expectations we had and we had HIGH expectations. Thank you for the wonderful experience.
Stayed 7 nights in Feb 2022
Verified

10/10 Excellent

Darren N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay at Island Pineapple

Both the interior and the exterior of the home were well kept. Plenty of room for the whole family. The pool area and the shaded areas downstairs were absolutely wonderful. The game room was a nice bonus for our youngest and a few of his friends who stopped by. Great house for a family. Location is perfect.We will be back next year.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Karen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

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!
Stayed 7 nights in Sep 2020
Verified

10/10 Excellent

mildred p.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Necesitaba mas limpieza

Necesitaba mas limpieza en la ropa de cama, toallas , pero la casa esta en muy buenas condiciones ,grande ,exelente ubicacion
Stayed 7 nights in Jul 2019

About the host

Hosted by Anna Maria Life Vacation Rentals

Host profile image
Family-owned and operated, Anna Maria Life Vacation Rentals offers everything you are looking for in an Anna Maria Island vacation rental company – exceptional properties and quality service with a personal touch. Whether it's a family vacation or a romantic getaway, AMLVR has something for everyone. From beachfront to bayside, you can choose from a quaint one-bedroom cottage, a waterfront condo with stunning views of the Gulf of Mexico, or a six bedroom pool home. AMLVR's vacation rentals offer authentic island living at an affordable price. Accommodations can be as upscale or as casual as you like and most are pet-friendly so you won't have to leave your furry family member at home.

Languages:

English

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