Where We Flip Flop

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Vacation Rentals We Love

The Amie House

Rooftop Ocean Views

The Amie House

The Amie House is perfectly situated a short 2 minute walk to the pristine white sands of Anna Maria Island’s North Shore. This luxury getaway is ideal for groups of families & friends. Enjoy the panoramic views of the ocean and island from the rooftop deck while enjoying early morning coffee or evening cocktails. Our spacious well equipped kitchen easily handles multiple cooks preparing gourmet feasts. The poolside patio is your perfect oasis in the midst of life.

The Barefoot Gypsy

Steps to Tampa Bay, Bean Point, Rod & Reel Pier

The Barefoot Gypsy

The Barefoot Gypsy is an enchanted cottage tucked in the north end of Anna Maria Island in the City of Anna Maria, Florida, mere steps to the white powder sands of Tampa Bay leading to Bean Point and the Gulf of Mexico. For a taste of Old Florida Charm, meander a few steps to the Rod & Reel Pier, built in 1947. This is a favorite of locals and visitors alike to see dolphins, manatee, and an abundance of shore birds. If you are looking for a special place to dine on local fare, you won’t be disappointed.

Bay Breeze Cottages

3 Cottages to Choose From, or choose them all for your larger group!

Bay Breeze Cottages

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer.

Beach Walk

Short Walk to Gulf Beaches

Beach Walk

2000 square foot home on beautiful Anna Maria Island, Florida, with all the upgrades and amenities. Short two block walk to the most beautiful white sand Gulf beach in the world, and if you want to kick back at home at your private in-ground swimming pool. There is a spa with jets off the pool.

Bimini Bay Breeze

Breezy and Beautiful Canal Front Home

Bimini Bay Breeze

Bimini Bay Breeze is a gorgeous canal front home with a focus on outdoor living. The back yard has a private dock for guests to put in kayaks or paddle boards and paddle right around the corner to Bimini Bay and beyond. A multitude of amenities include a five hole putting green on Astro Turf, ocean kayaks, pool and spa, outdoor kitchen near pool, stand up paddle boards, ping pong table, fire pit, and much more. Just two blocks from Gulf of Mexico beaches, it is an easy stroll with the provided beach cart and beach chairs.

Castaway Cottage

Cast Away Your Stress and Worries at this Adorable Piece of Old Florida

Castaway Cottage

Located a short leisurely stroll down a charming sandy pathway (or quick golf cart ride) from sparkling crystal clear water, the cottage locale also provides access to delicious island eateries or come home, grill your own cheeseburger in paradise, and dine around the pool. Don’t miss the blackened grouper and scallops at the renowned Rod & Reel Pier or a festive cocktail at the Sandbar!

Coral Cove

Walk to the Beach! Heated pool! 2 King beds! Florida charm!

Coral Cove

Welcome to your beach vacation paradise, Coral Cove! Situated on a quiet corner lot on the north end of Anna Maria, this elevated home offers a short walk to the white sand beaches of Anna Maria, a heated saltwater pool, multiple spaces for outdoor living and coastal Florida charm with all of the comforts of home.

Dragonfly

Just steps away from the Sands of Bean Point

Dragonfly

Extensively renovated in 2016, Dragonfly is a private retreat located right across the street from the sugary white sands of famous Bean Point Beach in Anna Maria, Florida. Glimpse sparkling turquoise waters from upper floor bedrooms, frolic in the pool with spa and sundeck, or create culinary delights in the gourmet kitchen with dual-zone wine cooler and Thermador gas range.

Halcyon House

Beautiful Beach-Font Home

Halcyon House

As seen in Coastal Living Magazine, this is a beachfront home on desirable Bean Point with with direct access to Bean Point Beach. You will enjoy panoramic views of the Gulf of Mexico from your two balconies. The house has a charming, cottage-style decor with an open floor plan. The living level has a full size, modern kitchen, a dining area, a half bath and a great room that opens up to a generous balcony for enjoying the breath-taking sunsets over the ocean. Halcyon, which means calm, peaceful, and tranquil, is exactly how you will feel during your stay at our house.

Holly Beach House

Close to Bean Point Beach, Private Saltwater Pool & Spa

Holly Beach House

Perfect location: Highly desirable NORTH END location in the City of Anna Maria. Just 5 minutes to the beach, and easy walk to the bay side, and to Pine Avenue with all its stores and restaurants. This beach house features cool tile floors, a 60″ flat screen TV, complimentary WiFi and YouTubeTV and fans in every room. Recently remodeled, there is a new metal roof and new windows to let the sun stream in. The backyard is fully landscaped with a 5 1/2 foot deep (at one end) salt water pool and an air bubble spa.

Island Hideaway

Adorable Vintage Anna Maria Cottage

Island Hideaway

Charming 2 Bedroom/1 Bath Cottage on the quiet North End, only a block to the Rod Reel fishing pier and restaurant! Just a short walk(2 blocks) to the Bean Point beach access, one of the most beautiful beaches on the island! Hide away in the lushly landscaped back yard oasis. Or, get out of the sun and relax in the very comfortable screen porch. This pristine vintage Anna Maria cottage is Island living at it’s finest. This cute cottage sleeps 6!

A Lazy River Day & Night

Island Vacation Home with Custom Lazy River Pool

A Lazy River Day & Night

Versatile 4 bedroom 3 1/2 bath home perfect for families or friends traveling together but may not have the same schedules. With 2 kitchens, 2 living/dining rooms and separate washers and driers, you can move about during your vacation at your own pace without disturbing the rest of your crew. There is so much for your enjoyment right here. We’ve included so many amenities! An interior door connects the two sides.

The Mahi Mahi

Cottage 1 of Bay Breeze Cottages

The Mahi Mahi

“The Mahi Mahi” comes with a full kitchen, 1 full bathroom with walk in showers and sleeps up to 4 people with 2 full queen beds. Perfect for a nice quiet vacation with a loved one!

My Private Beach

Entire Home is Anna Maria, Florida

My Private Beach

Key West style remodeled one level 4,571 square feet bay front beach house. Heated pool on .8 acre, 120 ft wide private beach. Tesla charger, 9.5 ft beam (width) boat slip across street (last one on right) with a massive shared dock with lights for fishing, kayaking, boating.

Our Blue Heaven

Short Walk to Holmes beach!

Our Blue Heaven

Our single story beach house is recently redecorated and includes a large, brand new heated pool. The home is located in a quiet, residential neighborhood and only a short, straight walk to one of the most beautiful beaches on the Gulf Coast.

Palm Beach on AMI

Custom Built with Beach View!

Palm Beach. onAMI

This custom built 5 Bedroom 4.5 Bath Heated Pool and Spa will make you feel right at home. At 3,200 sq ft, this home has plenty to offer allowing space for family and friends. Located on the North Shore of the Island, the retreat sits one house over from the beach for short trips back and forth.

Pelican Perch - 3

Tropical Paradise Cottage

Pelican Perch - 3

This quaint cottage is located “on the beach” on beautiful Holmes Beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4 with additional space for a pull-out. The cottage is hidden away on a dead end street away from it all, yet close to shopping and restaurants.

Pelican Perch - 4

Tropical Paradise on the Beach

Pelican Perch - 4

This quaint cottage is located “on the beach” on beautiful Holmes Beach. It is the upstairs unit (1 of 2) with a private deck and direct Gulf views. The cottage is very comfortable and sleeps 4 with plenty of space. The cottage is hidden away on a dead end street away from it all, yet close to shopping and restaurants.

The Redfish

Cottage 2 of the Bay Breeze Cottages

The Redfish

The Redfish” comes with a full kitchen, 1 full bathroom with walk in showers and sleeps up to 4 people with 2 full queen beds. Perfect for a nice quiet vacation with a loved one!

Rum Cove

Pool, Hot Tub, Water Equipment & Bikes!

Rum Cove

This magical home is a one-of-a-kind oasis on a one-of-a-kind island located right in the heart of Anna Maria! Rum Cove is placed perfectly within walking distance to all the prime entertainment spots! You will find restaurants, so many fun little shops to check out on historic Pine Avenue, cute places to grab a cup of java, donut, or waffle and of course, the many beach entrances are all just steps out your front door.

The Sailfish

Cottage 3 of the Bay Breeze Cottages

The Sailfish

“The Sailfish” is our largest unit with a full kitchen, 2 full bathrooms with walk in showers and sleeps up to 7 people with 3 full queen beds and a single bed. Perfect for a family!

Shell We Dance

Less than a Block from the Beach

Shell We Dance

Sweet vintage 1950’s bungalow/cottage with all the charm of the island! Located on the island’s much sought after north end. A short walk to Bean Point Beach, and just a few minutes more to Bay Front Beach and Park, and Rod and Reel Pier. Crystal clear waters of the gulf, white sands, and island breezes await.

Silver Palm Beach House

Expansive Private Backyard with Salt Water Pool

Silver Palm Beach House

It is just one of block (we have a long block) to the beach (short 5 min walk) and centrally located on Anna Maria Island in the city of Holmes Beach on a relaxing super friendly residential street! While the inside of the home is pristine, gorgeous, and beautifully decorated, the real feature of this home is the outdoor backyard oasis! It is private and lushly landscaped surrounded by beautiful palms, birds of paradise, a large coconut palm and tropical plants.

Simplicity Cottage

Traditional Home Located on Canal

Simplicity Cottage

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Summer Strand

Resort-like Pool; Rooftop Deck; Canal Front

Summer Strand

The spacious modern design boasts beautiful natural views of canals lined with mangroves and an abundance of bird and fish life, including the gentle manatees. The idyllic balconies are perfect for morning coffee. Fish from the private dock. Launch your kayaks and paddleboards right from the property. Take in the stunning sunsets while enjoying cocktails on the rooftop deck. Enjoy the pool and spa after a day out at the beach. All of this is just a short walk from the beach, making this the perfect getaway for nature lovers and water enthusiasts alike.

Surfside

Steps to the Gulf of Mexico Waters

Surfside

This fun and convenient private home is a favorite amongst guests who return year after year! Located in the heart of Anna Maria Island, “SURFSIDE” is close to all of the beach activities, shopping, dining, and entertainment. Amenities that set it apart include a LARGE, private fenced yard with heated pool and plenty of outdoor living area. The pool and deck have been recently resurfaced in September 2018! The home has been completely updated and furnished with well-appointed coastal decor.