Pineapplefish Luxury Vacation Rentals

a group of select luxury rental homes on Anna Maria Island which we have created to give you the best vacation experience ever!

We are a couple of Brits – Mike and Lizzie Thrasher.  We discovered Anna Maria on our own vacation in 2003 and fell in love with the island.  We like the great people, the simple way of living, the beautiful beaches and wildlife and wonderful houses.  In 2008, after working in design and organic food businesses for many years, we created Pineapplefish – this group of fun and luxurious rental homes.

We want you to have the same holiday experience that we have enjoyed. Each house has been created to the highest design and quality standards. Each is guaranteed to give you a wonderful experience. Whether it’s seeing the pelicans and dolphins in the gulf whilst you drink your coffee each morning, or enjoying the pleasures of Bimini Bay from your own dock, we promise you will take home many wonderful memories.

At each Pineapplefish house you will find many unusual and personal touches including information about our favorite restaurants and stores, and suggestions for good places to go explore.

As part of the pleasure of your stay, please visit Beach Bums – our island rental store on Pine Avenue ('Main Street').  Here you can rent the funkiest bikes, safe and unsinkable kayaks plus the best beach and baby equipment.  All are offered at a personal discount to our Pineapplefish renters.  Beach Bums is staffed by a great team including a retired sea captain and marine biologist Ask Captain Scott about his eco-tours of many local wildlife spots.

Most of all: go ahead and relax! And have a great Pineapplefish vacation!

Lizzie and Mike
Lizzie and Mike

 

 


 

Luxury Vacation Rental Listings:


101 75th St
Holmes Beach
Dreaming of an endless summer? Stay for a week or a month at what is perhaps one of the most dazzling beach front homes on An....more
Beds: 3
Baths: 3
101 75th St

522 Loquat
Anna Maria
Welcome to Lemonfish! Lemonfish is far too pleasant to be reserved only for a week. With the feel of an adult, upscale, e....more
Beds: 4
Baths: 3.5
522 Loquat

717 N Shore Dr.
Anna Maria
Welcome to Cherryfish! Imagine the most elegant and accommodating beach home. One without compromise. Combining stylish d....more
Beds: 3
Baths: 3
717 N Shore Dr.

422 Spring Ave.
Anna Maria
You can’t imagine anyone not falling in love with the exquisite Chillifish, a peaceful gem, decorated with the utmost attenti....more
Beds: 3
Baths: 2
422 Spring Ave.

335 Tarpon
Anna Maria
Sea grape trees, tropical flowering bushes and swaying palm trees surround this beautiful ocean-blue-colored beach villa on t....more
Beds: 4
Baths: 4 bath
335 Tarpon

111 Gull Dr.
Anna Maria
Plumfish Too good to be true? Plumfish is a cottage at the beach, a bungalow on the bayou and a private spot to call home.....more
Beds: 3
111 Gull Dr.