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Beach Front at “The Shore”

Welcome to The Shore —a beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to John’s Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

Waterfront Retreat• Private Pool• Golf• Ping Pong!

Dive into the ultimate summer getaway! Relax at this cozy waterfront cottage with a private pool, & a short drive to AMI’s white-sand beaches. 2BR/2BA with two living areas include a bright Florida room overlooking the canal. Enjoy ping pong and a putting green ⛳. Start your mornings with coffee on the dock, watching fish jump out of the water. Fast WiFi, workspace, beach gear, and a kitchen with cooking essentials. Perfect for beach days, family getaways, or a relaxing coastal escape.

2nd House from the Beach with No Roads to Cross

Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is thirty steps from one of the most pristine beaches on the Gulf of Mexico. The house is located on a quiet residential street near the north tip of the island. The front deck is a great place to watch the sunset. The house is clean, comfortable and well appointed. We welcome well behaved dogs and have a fully fenced yard for your pup to play.

KING Bed + AMI Beaches + Beach Gear!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

1/2 Block from Beach- Private Boat Dock & 30' Pool

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

This waterfront home with a private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage—set in a private, tranquil setting, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

Sea Vue -King Beds | Stunning Views | 2MI to Beach

Welcome to Sea Vue, a luxury Western facing home offering unparalleled water views, superior outdoor living, 5 bedrooms with dreamy hotel style bedding and activities for the entire group. Located just 2 miles to award winning St. Pete Beach & a short drive to the booming Downtown area this home is sure to exceed guest's highest expectations. Prepare to experience the highest level of customer service and indulge in your own private oasis inside and out.

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

Dockside Dreams - Pool, Spa & Waterfront Dock

Welcome to Dockside Dreams - Your Waterfront Paradise! Escape to our home nestled along the serene waters, less then 3 miles from Bradenton Beach. This is not just a vacation; its an aquatic adventure waiting for you! - Private Boat Dock - Dolphin and Manatee Sighting! - Close to the Beach! - Fully Equipped Kitchen - Outdoor Oasis: Soak up the sun on your deck or cook out by the water! Stays of 28+ Days welcome on request!