Anna Maria Island & Holmes Beach Vacation Rentals

Anna Maria Island luxury vacation beach rental homes with pools are our specialty!  Our Impressive large luxury vacation homes are the finest you will find anywhere. Considered the premier beach destinations in South Florida, Anna Maria Island should be right at the top of your vacation bucket list. Fishing, tennis, sailing, fine & local dining and terrific designer shopping are just a few of the activities available to our visitors. We invite you to call our knowledgeable Emerald Kite Destination Agent who will be delighted to share more about luxury rental homes and condos as well as  Anna Maria Island activities and fun things to do. 

Choose from Anna Maria Island & Holmes Beach Condos and Private Vacation Homes

Whether you are looking for a cozy beach cottage or a luxury Anna Maria Island beach house with pool & staff we have them all. With over fifteen years in the vacation rental business and thousands of satisfied customers we are Anna Maria Islands premier provider of quality luxury vacation rental pool homes. Anna Maria Island boasts year round wonderful weather & fun activities.  View award winning accommodations even better call our local Emerald Kite Agent who will strive to provide the best possible vacation rental options available for your dates. 

Explore Anna Maria Island & Holmes Beach

View of the Gulf from this Anna Maria Island Rental
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When it comes to dining, Anna Maria Island is best known for its fresh, local seafood however, there are plenty of options to suit any taste. Emerald Kite Vacation Rentals guides its thousands of annual visitors to the best local dining establishments on the Island and recommends the following restaurants located on and close to Anna Maria Island.


The Beach Bistro
6600 Gulf Drive, Holmes Beach, Florida - this is beachfront dining at its finest. Enjoy steaks, seafood, signature cocktails, and decadent desserts at this acclaimed restaurant, which has been honored by ZAGAT, Wine Spectator, and The James Beard Foundation. Open for dinner only. By Far one of Emerald Kites top dining picks on Anna Maria Island.


Sharky's Seagrill 
2519 Gulf Drive North, Bradenton Beach, Florida.
Owned and operated by a European-trained chef, Sharky's offers seafood, steaks, pastas, and a full bar. The restaurant opens at 4 p.m. — just in time for happy hour! — and sandwiches and light bites are available at the bar until midnight.


The Sign of the Mermaid 
9707 Gulf Drive, Anna Maria, Florida
Nestled in a quaint, antique-filled home, The Sign of the Mermaid is a local favorite. The restaurant has a unique fusion menu, offering seafood favorites, vegetarian options, and Asian-inspired dishes. They serve breakfast, brunch, lunch, and dinner, and also have a full beer and wine list.


Mr. Bones
3007 Gulf Drive, Holmes Beach, Florida
Home to some of the most famous baby back ribs in the country, Mr. Bones is the place for BBQ on Anna Maria Island. Additionally, they also offer tasty vegetarian and vegan items, and are open daily for lunch and dinner.


Joe's Eats & Sweets

219 Gulf Drive South, Bradenton Beach, Florida
Craving something sweet? Joe's offers outrageous ice cream flavors, including key lime cheesecake, pineapple coconut, and white chocolate peppermint bark, just to name a few. They also have sorbet and sugar-free options, and are open until 10 p.m.

Anna Maria Island offers a great range of shopping options. From basic necessities to gifts and souvenirs and high end imported designer shopping.


Consider it Done
Consider it Done is a terrific concierge service utilized by  Anna maria Island vacationers. Services include grocery shopping, errands, yacht charter, babysitting and much much more. Nothing is to much trouble and this great company bends over backwards to ensure all your vacation needs are met and exceeded! Call your Emerald Kite Destination Agent to learn more about this amazing local service.


Publix is Anna Maria Island's full-service grocery store. Located at 3900 East Bay Drive on Holmes Beach, it offers a bakery, deli, and fresh fruits and vegetables.


Specialty Boutiques and More
Stroll along Pine Avenue for boutiques galore. Pine Avenue also intersects with the Historic Anna Maria City Pier, where you can catch a fabulous glimpse of the bay. Additionally, Holmes Beach offers plenty of small gift shops, cafes, jewelry stores, and art galleries.


Outlet Malls
If you venture 30 minutes outside of Anna Maria Island, you'll find the Ellenton Outlet Mall, which features over 100 spectacular stores.Emerald Kite the leading supplier of high end vacation rentals brings thousands of visitors to Anna Maria Island from the U.S.A and International visitors just wanting to shop till they drop and fill their empty suitcases before they head back home. 

Anna Maria Island is regarded as one of Florida’s most laid-back locales, but that doesn’t mean it lacks excitement! There are plenty of activities for the whole family to enjoy. Check out our list of Anna Maria Island vacation activities. 


There are plenty of options for golfing near Anna Maria, and some of the best are in nearby Bradenton. For a quick round, visit the Pinebrook/Ironwood Golf Course. For a more challenging game, we recommend the Waterlefe Golf and River Club, which is also in Bradenton (and home to many PGA events).

For Kids and Teens
Anna marias Yolo Adventures offers exciting activities for the whole family, including parasailing, sunset cruises, and dolphin watching. You can also spend a day at the Clearwater Marine Aquarium, or rent bikes, boats, and kayaks from Just4Fun.



No vacation is complete without relaxation. For the ultimate spa experience, we highly recommend Acqua's Aveda on the Beach Spa, which offers hair design, massage, skin care, and men's services. Another great choice is the full-service Blue Door Spa and Salon, voted "Best Spa" by the Bradenton Herald for four years running.

Anna Maria Island is situated between peninsular Florida and the Gulf of Mexico, just south of Tampa Bay. It's divided into three cities — Anna Maria occupies the north, Holmes Beach claims the center, and Bradenton takes up the southern portion of the island. Learn more about transportation on Anna Maria Island below:


Airports Close to Anna Maria Island
The Sarasota-Bradenton International Airport is located just 15 miles away, and the Tampa International Airport is 51 miles away. While the Sarasota Airport is closer, the Tampa Airport has a wider variety of air carriers.


Anna Maria island FreeTrolley
The Anna Maria Island Trolley is absolutely free, and offers an efficient way of exploring both Anna Maria Island and its posh sister barrier Island,nearby Longboat Key & St Armand's Circle. The Anna Maria Island trolley operates daily from 6 a.m. to 10:30 p.m. and many Emerald Kite guests forgo rental cars and pick up a driver or UBER at the airport and save, save, save! Following in the footsteps of world class resorts such as Vail Colorado & Positano Italy Anna Maria Island boasts this free transportation service resulting in guests returning year after year! The shuttle leaves every 20 minutes or so and many of Emerald Kite Anna Maria Island luxury vacation rental homes are situated within steps of the trolley stops. This incredible service is ideal for teenagers and those to young to drive rental cars. Young people love the freedom and independence to get around and parents simply take a well earned break from driving the young ones around!

Wherever you stay on Anna Maria Island the trolley stops are between 2 - 4 blocks apart with a few exceptions. Enjoy a shaded seated area at your stop and remember the trolley is air conditioned!  While the Anna Maria Island trolley (right now) is totally free the Longboat Key Trolley charges 75c. What a deal though. Pick up the trolley at Coquina beach and enjoy a breathtaking drive down picturesque Gulf of Mexico Drive, Longboats key main road that frames the Gulf of Mexico. Some of Florida's most amazing, ritzy beach homes are situated on Longboat key and you may spot the odd celebrity heading down to the beach.  Depart from the trolley pretty much anywhere along Longboat Key and enjoy the quiet, unspoiled and frankly underestimated world class beaches. No crowds here! Take the trolley further down Gulf of Mexico drive where you can visit St Armand's Circle, a fun and sophisticated  European style open plaza with an abundance of upscale boutiques, grocery stores, and fine and casual dining. Remember to check the trolley return times from St Armand's Circle as 11.00 pm is typically the last departure but holidays and weekends may vary.

Rental Cars
If you enjoy the convenience of a car — or you want to travel to other destinations, such as nearby Sarasota — you can find rental cars at nearby airports . Call your Emerald Kite agent today who will be delighted to assist with all your rental car needs while staying on lovely Anna Maria Island.