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USA Florida Florida Gulf Coast Anna Maria Listing #13588

Pineapple Cottage - Anna Maria, FL

13 reviews
Max occupancy: 8 2 King Bed, 1 Queen Bed, 2 Twin Bed 4 bedrooms 3 bathrooms Dog-friendly  (25 lb weight limit) 
407 Spring Ave., Anna Maria, FL 34216

Dog-friendly cottage w/ private heated pool - minutes from beaches & more!

You're sure to fall in love with this charming, dog-friendly Anna Maria cottage! Enjoy a fantastic location, beautiful beaches, and perks like a private heated pool.

You, your loved ones, and dogs under 25 pounds (for a small nightly fee) will adore this home on Spring Avenue. The street stretches to both the Gulf of Mexico in the west and Tampa Bay to the east, so you're only a two-block walk from multiple beaches! You can also explore the shopping, dining, and sightseeing of Pine Avenue, or visit the historic Anna Maria City Pier. Up to four vehicles can park at this home, but if you'd prefer to get around like a local, use the free trolley to explore!

After a long day out, relax in the living room while watching the flatscreen TV or surfing the free WiFi. The well-appointed kitchen features stainless steel appliances, gorgeous granite countertops, and a dishwasher. Cook up a delicious meal with the help of the gas grill outside, then spend the evening in the gorgeous backyard. With beautiful landscaping, a covered patio, and a private pool, it's like having your own private tropical paradise!

For an authentic Florida beach cottage experience, reserve your stay at the Pineapple Cottage today!

*Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!*



Pool : Private

Central AC

Heated pool

Washer/dryer : Private










DVD player

Wireless router




Gas grill : Private


13 reviews

Julie K. Jun 2019
Lovely, clean little cottage with nice backyard and pool. Great location—able to walk to beach, restaurants and shopping.
Lisa M. Jun 2019
Our family of five adults and two children spent a week at the Pineapple Cottage. The house was very clean, the furniture was either new or in great condition. I have a bad back and was pleasantly surprised by how comfortable my bed was and how well I slept at night. I really loved the close proximity to the shops and the beach; this was a perfect location. The pool was fantastic and consisted of multiple areas for the adults to congregate while the kids played and splashed around in the pool. This was a beautiful, well maintained and clean home, would definitely stay there again!
DeVismes S. May 2019
Great house and great location! You won’t be disappointed!
Laura W. Apr 2018
It was a beautiful house with a great backyard. Now that I've looked at other properties, I feel that is much over priced for a week's vacation based on similar rentals in the area. Anna Maria has so much to offer.
Ashley B. Apr 2018
If you've never been to AMI, this house is in a great location! Set back a block from pine but still so close to the main downtown area. Amazing pool area and walking distance to both beaches. Would definitely return!
Scott S. Aug 2017
We've enjoyed all 3- rentals ( over several years) and have always had a great experience dealing with your company. My entire experience, from reservation booking, check-in, and service request were all handled professionally & with courtesy. Very impressed with your staff!!
Eric V. Aug 2017
We booked our second trip out to the Pineapple Cottage before we even left! What a house, the back yard was loved by each and every person in my family. The kids especially enjoyed the night swimming in a rainbow lit pool. The four bedrooms gave everyone their own space, which my wife and I enjoyed the most. Even better than the house it self was the location of it. Pineapple Cottage's proximity to both the shopping on Pine Ave, just one block over, and being smack in the middle of the bay and beach heaven. We can't wait to go back!
Sarah K. Apr 2017
Just left the beautiful Pineapple Cottage. The house had quite a few issues when we first arrived but Island Real Estate took care of them quickly. The house is quite small and the washer and dryer are not conveniently located. The pool is amazing but difficult to get to unless you go through the bedrooms or around the house. Also the "4th" bedroom with the trundle bed is really a far stretch as a bedroom. They took an open desk area and made it into a bedroom. There's also no pantry closet so if you plan to buy a lot of food there's not a lot of storage. Absolutely can't beat the location of the home or back yard with the pool. The covered porch on the back yard and landscaping around the pool made it feel like an oasis.