It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling... View all property information

The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and... View all property information

The Shady Mango was originally built in 1925. According to local history<BR>the heart pine used in constructing the original house came by steam boat<BR>to the City Pier and was hauled by horse-drawn lorry up Pine Avenue to the<BR>home's present site.<BR><BR>In 2004 the home was given a major... View all property information

Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view... View all property information

4 Bedroom 3 Bath Large Family Beach House Just 200 steps to the most Beautiful Beach in the World. Crystal Clear waters with plenty of fishing, wildlife and swimming. Great for Multi-Family Gatherings, Weddings, Family reunions or just plain fun. With a 2 bedroom 1 attached apartment for... View all property information

WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical... View all property information

Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 12 people. This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear, from all living spaces. With 5... View all property information

Start your relaxing vacation at Beach Walk, located just a block from the white sand beaches of Anna Maria Island. This lovely two bedroom, one bath, home has just been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during your... View all property information

Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower and comfortable furnishings. The... View all property information

Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that were not enough, it also has a heated pool and is on a... View all property information

This adorable remodeled duplex sits quietly in the highly desirable north end of the Island in the City of Anna Maria. It is a short walk of only a little more than a block to the Gulf beach where the sand is sugary white and the water is a beautiful blue-green color. There is a King in the... View all property information

When you 'have anna maria' on your mind, you'll want 'hav'anna hideaway' for your vacation home. This newly constructed 4 bedroom, 4 bath home is located just one short block to the beautiful and sparkling gulf beach. The main floor of the home consists of an open concept living room, kitchen with... View all property information

209 Spring - Private home 3 Bedroom / 2 Bath with private pool, maximum occupancy of 8 people. Spring into the waves!~ 209 Spring. 3 bedroom, 2 bath raised home in quiet, residential area of Anna Maria. Private pool. Pool heat optional @ $20/day. 1 block to the beach. Large screen high def... View all property information

Ahhhhhh. Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! <BR>Vacationers, dreamers, honeymooners, would-be family-reunion planners and... View all property information

Steps from the white sand beaches of Anna Maria, this four-bedroom, three bath, elevated house is just the place to build sand castles and memories! Located on Pine Avenue in Anna Maria, this charming beach vacation rental with a newer backyard pool is beckoning you to start your vacation now. A... View all property information

Beachy Keen 408 - Private home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. Here delightful and fun Caribbean Cool décor welcomes you to the sub tropic cozy of Anna Maria Island. A charming island home within easy walking distance to the beach, offers an ideal location... View all property information

BON AMI will be your 'good friend' after a vacation stay. Located on the north end of Anna Maria Island and a short distance to Bean Point, this heated pool stilt home will beckon you back year after year! Beautifully decorated, this three-bedroom, two-bath vacation rental is spacious, airy, and... View all property information

Lazy Lagoon has it all! This remodeled 2 bed/2 bath home is anchored in splendid the north end of Anna Maria on a deep water canal with dock, has its own heated pool and hot tub, and is a short walk to the beach, restaurants and free island trolley. The serene canal-front setting coupled with quiet... View all property information

Start your relaxing vacation at Sea Oats, located just a block from the white sand beaches of Anna Maria Island. This lovely two-bedroom, one-bath vacation rental has just been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during... View all property information

The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm... View all property information

Look no further for the perfect vacation rental! This three bedroom vacation rental is located on the serene north end of Anna Maria Island. Tastefully decorated with beautiful beach décor, and boasting a wonderfully open living and dining space, this vacation rental creates an exceptionally... View all property information

Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just around the corner from the Rod & Reel Pier, Bayfront Park, and just a couple of blocks to Fabulous Bean Point Beaches and Sunsets. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor lounging... View all property information

Great Ground Level 3 Bedroom/2 Bath Home with a Heated Pool located in the quiet north end and just 3 houses to the beach!! King-Sized master bedroom with TV, Queen in the 2nd Bedroom with TV, and Twins in the Third with TV. Cable TV, DVD, and Flat Screen TV in Living Room. High speed Internet,... View all property information

**SPECIAL** 20% off bookings in September, October and November! Ask about the discount when booking! Anna Cabana A is the perfect getaway! Located on the north end of Anna Maria Island and just a short stroll to the beach, this cute bungalow beckons you to stay and relax. This adorable vacation... View all property information

Toes in the Water is an amazing ground level 4 bedroom/3 bath home, just 90 Steps to the beach! This north end gem boasts a large, private, and heated pool with swim-up tiki table. Quiet setting in the beautiful north end of Anna Maria, and located west of Gulf Drive for easy beach access with no... View all property information

Completely remodeled 2 bedroom/2 bath duplex, with a beautiful tropical HEATED pool, just over a block to the beach, and the free island Trolley! There is a King and a Queen bedroom in the North Unit, and a King and Twin Bedroom in the south unit. Both units also have a queen sleeper sofa. Sleeps... View all property information

103 Pelican - Private canal home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. At this spacious, family friendly home with private pool, grab your fishing pole, take the hand of a child and meander to the private dock, cast a line while dangling your feet and spending the... View all property information

Beachcombers is a spacious 3 bedroom/2 bath home with all of the 'Old Florida Charm' you could ask for. Situated on Spring Avenue, just a couple of blocks to the Gulf of Mexico on Anna Maria's beautiful north end! Easy walking distance to many shops, restaurants, the Anna Maria City Pier and a... View all property information

Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information

Located in the heart of Anna Maria, a gorgeous and spacious Mediterranean style 4 Bedroom/3 Bath Home with a Heated Pool in a very private and peaceful setting. Only steps to Pine Avenue shopping and Trolley Stop, 2 blocks to the Beach, and walking distance to the Pier. The open floor plan features... View all property information

This great 2 Bed/2 Bath Home with Private Heated Pool resides in Anna Maria and is only one block to the beach and has no busy streets to cross to get there. You can quickly make your way to the Gulf Sands and to all of the great shops and restaurants that Anna Maria and Holmes Beach have to offer.... View all property information

Located directly across from Tampa Bay, this gorgeous new custom luxury vacation rental looks out onto the beautiful bay waters from multiple large balconies. A rooftop deck provides outstanding 180 degree views of the turquoise waters, as well as the Anna Maria City Pier and the Sunshine Skyway... View all property information

744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Live the Florida lifestyle in this beautiful, comfortable 3 bedroom, 3 bath private home with private pool and with screened lanai. The home is located on Anna Maria Island in the prestigious north... View all property information

This adorable remodeled duplex sits quietly in the highly desirable north end of the Island in the City of Anna Maria. It is a short walk of only a little more than a block to the Gulf beach where the sand is sugary white and the water is a beautiful blue-green color. There is a King in the master... View all property information

The adorable Coastal Cottage, located in the laid-back city of Anna Maria, is the perfect place to take a totally carefree vacation. The white sand beach of Anna Maria Island and the azure blue waters of the Gulf of Mexico are only a short stroll from this delightful three-bedroom, two-bath... View all property information

Anna Maria Island Oasis- Pamper yourself by staying in this brand new Island home with vaulted ceilings, custom tile and cabinetry, along with your own private heated pool. This home offers 4 Master Bedroom Suites each with it's own private Bath. Each bedroom has a King bed and each en-suite bath... View all property information

Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long... View all property information

Beautiful ground level 3 bedroom/2.5 bath home, with a quiet north end location only a block to the beach! There is a King in the master with a private patio, a Queen in the second, twin beds in the third, and a queen sleeper sofa in the sunroom (which has blinds for privacy), all accommodating up... View all property information

This cute beachy Canal front 3 bedroom, 2 bathroom Home has a Pool and a boat dock and is just 2 short blocks to the beach. Kitchen includes a dishwasher and microwave. Enjoy the Gulf breezes down the canal from the screened lanai or the back yard area. Bring your boat and go fishing or just enjoy... View all property information

We call this home "A Time Out" cottage and you will definitely say, "We deserve a time out at this place!" This completely remodeled private home on Anna Maria Island's north end features four bedrooms, two baths and the most wonderful tropical and lush pool and patio area! On the main level of... View all property information

Beautifully remodeled 3 bedroom/2.5 bath home with luxury amenities on the North End of Anna Maria, just 4 houses to Bean Point, one of the quietest beaches on the island, and 2 blocks to the famous Rod & Reel Pier! Private Backyard with Heated Pool, and an open floor plan with vaulted ceilings!... View all property information

**SPECIAL** 20% off bookings in September, October and November! Ask about the discount when booking! Anna Cabana B is the perfect getaway. Located on the north end of Anna Maria Island and just a short walk from the beach, this cute bungalow beckons you to relax and stay a while! This adorable... View all property information

Welcome to Canal Place, an inculpable island home that is outfitted to offer occupants an unforgettable vacation experience! In your privately cultivated backyard is an assemblage of accessories providing plenty of options for fun in the sun. There is a heated pool, hot tub, kayaks, boat dock,... View all property information

Looking for that place to kick back and relax your cares away? Check out ‘Triple Play Guest House.' There's a triple chance to play: (1) walk to the beach, (2) lounge in the pool or spa or patio or (3) launch a kayak, fish or just relax on one of our two docks on the canal. Nothing quite compares... View all property information

Completely Remodeled 3 bedroom/2 bath home with private Heated pool. Beautiful new tile, Granite countertops, all new appliances, and living room overlooking the heated pool. Bright, open kitchen, dining and living area! Sleeps up to 8. 1500 Sq. ft. 204 Archer Way, Anna Maria 3 Bedroom/2Bath... View all property information

Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information