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Pineapple Cottage, walk to the beach & Pine Ave, tropical oasis pool and spa.

Photo gallery for Pineapple Cottage, walk to the beach & Pine Ave, tropical oasis pool and spa.

A covered outdoor patio with a pool, seating area, and lush greenery.
A modern kitchen with white cabinetry, a granite countertop, and a central island with wooden chairs.
A pool area with two circular pools, surrounded by palm trees and a building with a yellow facade.
A bedroom with a bed, a ceiling fan, a window with blinds, a door leading to a balcony, and a painting on the wall.
A coastal residential area with houses, a swimming pool, and a view of the ocean.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Discover nearby landmarks
    Near Bean Point Beach

Popular amenities

  • Balcony or patio
  • Hot tub on site
  • Private pool
  • Outdoor barbecue
  • High-speed internet
  • Air-conditioning

Explore the area

View in a map
Anna Maria, FL
  • Place, Anna Maria Island Museum and Historical Park
    ‪3 min walk‬
  • Place, Bradenton Beach
    ‪6 min walk‬
  • Place, Anna Maria City Pier
    ‪8 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪41 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Single Bunk Bed

MASTER BEDROOM

1 King Bed

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Porch or lanai

Add dates for prices

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  • Kitchen
  • Washing machine
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9.6 out of 10, Exceptional, (37 reviews)
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About the area

Anna Maria

Located in Anna Maria, this holiday home is 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.
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Map
Anna Maria, FL

What's nearby

  • Anna Maria Island Museum and Historical Park - 3 min walk - 0.3 km
  • Island Players - 6 min walk - 0.6 km
  • Bradenton Beach - 6 min walk - 0.6 km
  • Anna Maria City Pier - 8 min walk - 0.7 km
  • Bean Point Beach - 18 min walk - 1.6 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 33 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬6 min walk
  • ‪Anna Maria Island Beach Cafe - ‬8 min drive
  • ‪The Ugly Grouper - ‬6 min drive
  • ‪Ginny's & Jane E's - ‬6 min walk
  • ‪The Waterfront Restaurant - ‬5 min walk

Frequently asked questions

Does Pineapple Cottage, walk to the beach & Pine Ave, tropical oasis pool and spa. have a pool?

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

Is Pineapple Cottage, walk to the beach & Pine Ave, tropical oasis pool and spa. pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Pineapple Cottage, walk to the beach & Pine Ave, tropical oasis pool and spa.?

On-site parking is available at the property.

What time is check-in at Pineapple Cottage, walk to the beach & Pine Ave, tropical oasis pool and spa.?

Check-in begins at 4:00 PM.

What time is check-out at Pineapple Cottage, walk to the beach & Pine Ave, tropical oasis pool and spa.?

Checkout is at 10:00 AM.

Where is Pineapple Cottage, walk to the beach & Pine Ave, tropical oasis pool and spa. located?

Situated near the beach, this holiday home is within a 10-minute walk of Anna Maria Island Museum and Historical Park and Bradenton Beach. Bean Point Beach and Anna Maria Beach are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 23 out of 25 reviews
Rating 8 - Good. 2 out of 25 reviews
Rating 6 - Okay. 0 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Excellent Accommodations and Location

My family and I absolutely loved staying here. It fit every one of our needs and you just can’t beat the location.. will definitely book here again
Stayed 4 nights in Aug 2020
Verified review

10/10 Excellent

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

Awesome place to stay!

Book now and you will not be disappointed. Great house, pool and location to the beach and restaurants!
Stayed 4 nights in Nov 2023
Response from VrboOwner on 1 Dec, 2023
Thanks for your review of 'Pineapple Cottage' on AMI, Steve! It truly is a perfect place for an island getaway.
Verified review

10/10 Excellent

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

Amazing AMI

Great property in a wonderful location. The outdoor space and pool were absolutely perfect!
Stayed 4 nights in Aug 2023
Response from VrboOwner on 8 Sept, 2023
Thanks for staying at 'Pineapple Cottage'! Happy to hear you enjoyed the pool and outdoor space.
Verified review

10/10 Excellent

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

Pineapple house

The house is excellent. The pool is incredible! An overall very relaxing place for a vacation. Perfect location on the island for dining and shopping. We would definitely stay here again.
Stayed 4 nights in Jul 2023
Response from VrboOwner on 4 Aug, 2023
So happy to hear you thought 'Pineapple Cottage' was excellent and that you had a relaxing vacation! Hope to see you again soon!
Verified review

10/10 Excellent

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

Wonderful property

Amazing house and outdoor pool area. Had a wonderful 4th of July stay! Walking distance to everything you want/need!! Very attentive property manager that checked in with us periodically to make sure we had everything we needed.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and an amazing pool. The property was very clean and beautifully decorated. The best part is the the pool and backyard entertaining area. Awesome! We noticed an issue with the pool on our third day, and once we called, someone came out very quickly to address the matter. When some parts needed to be ordered for the pool, the pool maintenance guy configured a way that we could still use the pool and we were never without it.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

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

Really nice stay!

There were 4 of us (55+) women who came in to attend a birthday party for our friend in Bradenton. The Pineapple House was perfect for us…from clean, to space, to privacy to location to restaurants, shopping and the beach…everything was a walk or golf cart away! We LOVED it!
Stayed 4 nights in Jul 2022
Response from VrboOwner on 30 Aug, 2022
We appreciate being able to host such wonderful guests and thank you for your feedback! We would highly recommend Kimberly to any hosts.
Verified review

8/10 Good

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

Amazing cottage

We had an amazing stay . Location was on point. The island was like no other I have ever witnessed!!! Only issue was the air conditioning quit on us our last night .
Stayed 6 nights in Jul 2024
Verified review

10/10 Excellent

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

Perfect location and backyard

This house was better than expected! The backyard is very private and nicely designed. Everything was brand new.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

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

perfect beach house for our family

Our family of six adults and two young children loved this house. The lighting was great for my husband who is vision impaired. The pool is spectacular and almost as much fun as the beach. great location and vibe. a winner
Stayed 4 nights in Jun 2024
Verified review

10/10 Excellent

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

Fam vacay

Loved Pineapple Cottage! Very well appointed decor. Loved the ceiling fans. Beds/pillows were very comfy. Had a little issue with the pool but it was handled quickly. Salty Mermaid Co. was fantastic to deal with.
Stayed 6 nights in Jul 2024
Verified review

10/10 Excellent

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

A relaxing oasis

I recently stayed at Pineapple Cottage with my extended family, including an infant. The location was great! 5 minutes walking distance to the beach and shops/restaurants. The pool area and backyard are amazing! We went outside every chance we got and enjoyed the hot tub and outdoor tv so much. There are 3 full bathrooms, one of which has a bathtub, which was convenient for bathing our baby. Highly recommend this home for larger groups!
Stayed 5 nights in Nov 2023
Verified review

10/10 Excellent

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

Great Property.

This house is in a great location, 3 blocks to the beach, restaurants, and 3 blocks to the pier and other amenities. It is charming, spacious and has everything you need to make your stay easy, effortless and pleasant. The back yard is a little oasis, very enjoyable, the swimming pool is beautiful, and the hot tub was a hit with my family. Everything is super clean: the linens, the whole house is spotless. It is a family friendly property. We will definitely come back!
Stayed 6 nights in Aug 2023
Response from VrboOwner on 8 Sept, 2023
'Pineapple Cottage' can not wait to host you again, Maggie. The back yard is the perfect personal oasis, glad to hear you took advantage. Come back soon!
Verified review

10/10 Excellent

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

Family Vacation

The property was exactly as it looks online. The pool was great, very clean, beds were comfy, plenty of towels. We rented a golf cart which was a great idea so we didn’t have to use the car to get around the island. Beaches were breathtaking, thank you for such a great experience. The only thing I couldn’t find was a cutting board.
Stayed 6 nights in Jun 2023
Response from VrboOwner on 28 Jul, 2023
Thank you, Nathan, for the 5 star review of your recent stay at 'Pineapple cottage'! Glad to hear you all had a great experience on Anna Maria Island. Hope to see you all return soon :)
Verified review

10/10 Excellent

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

Best vacation

My overall experience of this property was excellent!! Loved the pool, the location to the beach and to Pine street. Enough parking for our group was wonderful!! No complaints at all!!
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

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

Nice place

It was a beautiful property but a little smaller than what we expected. Glad my son in law backed out in the last minute. I should have read the bedrooms better, but that’s my fault. They don’t offer any beach chairs or coolers which was disappointing because all other rentals did, but we survived. The rental company was fabulous!
Stayed 6 nights in May 2022
Verified review

8/10 Good

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

Great location and communication with owner.

We absolutely loved the home and the location of this property. The owners were wonderful to work with and we appreciated their feedback when needed. It was wonderful to have been extra propane tanks available for the grill, as the gas did run out while we were there. It was great to be able to put a new one on with ease and not worrying about where to fill one. Couple items of concern: The pool was nice and clean however the hot tub was not warm at all. We followed the directions exactly how they were left to get it warm, and it never worked the entire week. It would’ve been nice to have a variety of pans and cookie sheets to cook with as we ate in every day. There is not a pantry and hardly anywhere to store food, but we made it work. A couple concerns for us as we stayed is the appliances as well. The stove and oven do not work very well at all. Many times the burners would not get hot enough and the oven would take an extremely long time to warm up and then cook food. Over we had a wonderful time because AMI is a wonderful location but some of these items would have made the trip even better if they weren’t issues.
Stayed 7 nights in Apr 2022
Verified review

10/10 Excellent

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

Great rental

We stayed here in November and had a great stay! The pool area is awesome and very private. The house was very nice, too!
Stayed 5 nights in Nov 2021
Response from VrboOwner on 2 Mar, 2022
It was a pleasure being able to host great guests. We appreciate the feedback and hope that when you return you remember us! Would recommend Becca to any VRBO host.
Verified review

10/10 Excellent

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

Beautiful cozy retreat!

The property exceeded expectations! It was so clean and had a great set up for a girls trip! Lots of privacy with backyard pool/jacuzzi. The property manager was extremely responsive with questions. The only question is , Are you selling anytime soon?!
Stayed 4 nights in Sep 2021
Response from VrboOwner on 27 Jan, 2022
Happy to hear you had an amazing girls trip! We pride ourselves on giving personalized service. We thoroughly enjoyed being given the chance to host you and in hopes, you return!
Verified review

10/10 Excellent

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

Amazing all around!

We stayed at the pineapple cottage for a girls trip- the location is amazing. So close to pine street and the beach! The house is a perfect layout and space- the backyard was our favorite part! It truly is a peaceful, tropical, private oasis! We will definitely be coming back!
Stayed 4 nights in Aug 2021
Verified review

10/10 Excellent

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

Great location

This is our third time staying on the island. We love the location of the house. Super close to the beach and The Donut Experiment which is my husband’s favorite. The pool and hot tub was great! Our family enjoyed spending time outside by the pool and if we wanted to get out of the sun. Great sitting area outside with a tv. We will definitely book this house again!
Stayed 5 nights in Jun 2021
Verified review

10/10 Excellent

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

Quiet in paradise

Great home with super quiet back patio and pool area. The house is beautiful and clean. The location is perfect since it’s so close to beach areas. Fantastic shops and restaurants close by within walking distance. We will be looking to stay there again. The Thompson’s
Stayed 7 nights in Mar 2021
Verified review

10/10 Excellent

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

Pineapple cottage is awsome

Everything about our visit was awesome! The house looks small from the street, but is very spacious inside. Everything we needed was available to us. Very clean. The backyard/ entertainment area was PERFECT!! Would highly recommend!!
Stayed 4 nights in Nov 2020
Verified review

10/10 Excellent

Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness
Stayed 5 nights in Apr 2025
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