Families will LOVE Anna Maria Island! Lots to do, kid-friendly beaches, restaurants that welcome kids and adults alike, and we’re a day trip from Disney – Beach and Mouse in one house! Check out our Family Fun posts to get ideas for planning your visit to Anna Maria Island today!
If you’re looking for a family friendly restaurant try checking out one of the island’s waterfront restaurants featuring live entertainment and a comfortable inviting atmosphere.
Things To Do
If you’re getting tired of swimming or visiting the many beaches in the area there are plenty of public pools to visit as well. Take a trip to one of the area aquariums to get a close up look at the sea life! A short trip to the Florida Maritime Museum will be both educational and fun for the whole family.
If you’re visiting during the summer there are plenty of additional options, such as participating in the turtle watch which takes place between May 1st-October 31st. The kids can learn about the local turtles and see some of the nesting grounds that are penned off with stakes and tape right on the beaches. Kids can also learn to surf with the kid’s summer surfing camps!
Take a water shuttle trip on the Island Pearl to various locations and maybe even see some dolphins! Or for those who prefer solid ground the Anna Maria Island Trolley the Crown Jewel will take you around the island for free!
If you would like you can take a video tour of Anna Maria Island before you visit to get acquainted with some of the sights and locations!
Accommodations and Vacation Rental Properties on Anna Maria Island
Island Real Estate is the best choice when looking for the perfect family fun accommodations. With the largest inventory of vacation rental homes on Anna Maria Island, Island Real Estate is sure to please with great customer service and a knowledgeable staff.
There are several great Anna Maria Island Holiday Events this year! Throughout December there will be celebrations across the island’s three cities.
Anna Maria Island Holiday Events 2016
Get into the spirit of the holiday with these fun family events.
Holmes Beach Holiday Open House and Tree Lighting
December 2nd will be the Annual Holiday Open House. This event is organized by the Anna Maria Island Chamber of Commerce and sponsored by local businesses. From 5-8pm walk around the Holmes Beach Shopping District for snacks and libations while local businesses stay open late. These businesses will have specials going on too!
At 6pm watch the annual lighting of the tree in front of the Chamber at 5313 Gulf Drive. Santa and his sleigh will also make an appearance, so everyone better be on their best behavior.
The Chamber will provide lite snacks, coffee and wine. Next door, Eat Here restaurant will be showing the movie “A Miracle on 34th Street” in addition to serving mulled wine.
Bring a toy to donate to Toys for Tots. There will be a donation box at the Chamber of Commerce.
Anna Maria Pine Avenue Holiday Treasure Walk
Celebrate the holiday in Anna Maria on December 9th with the Holiday Treasure Walk. Pine Avenue and Gulf Drive Merchants will be open late from 5-8pm with special sales and tasty treats.
Stop by The Studio at Gulf and Pine for refreshments from the Sandbar Restaurant. Additionally, Roser Church Joyful Noise Children’s Choir will be performing at the Historical Society at 6pm.
There may even be an appearance from Santa too!
Bradenton Beach Christmas on Bridge Street
Christmas on Bridge Street is an annual family friendly event with tons of entertainment and holiday fun. The event will take place December 17 from 4:30-8:30pm.
Enjoy music from Russ Adams Project, The Dickens Carolers, and more!
There will be a kids crafts and cookie bazaar where children will be selling their baked goods and handmade gifts.
In addition to the gift market, you’ll find a wreath raffle, and gift basket silent auction.
You’ll also find a Hot Chocolate Bar, Snow and Santa.
Enjoy Christmas on Anna Maria Island with these fun events for the whole family!
Island Real Estate has what you need for an Anna Maria Island Mediterranean style vacation! Why travel across the world for beautiful beaches when they are waiting right here on the Florida Gulf Coast?
Anna Maria Island Mediterranean Style Vacation for Less
A Mediterranean vacation is full of relaxation, blue seas, and beautiful sunshine. The countries around the Mediterranean offer great sight seeing and interesting history too. All of these things are on Anna Maria Island! An exotic destination, with perfect weather and fun leisure activities is waiting for you. All you need is the quintessential Mediterranean style beach rental to set the tone for your Anna Maria Island vacation. Best of all, you won’t break the bank during your coastal siesta to Anna Maria Island!
This beach rental is about two-three blocks from gulf beaches, and one of the island’s most popular public accesses. Under the Tuscan Sun offers 3 bedrooms and 3 bathrooms with plenty of space for up to 9 guests. Not only will you be close to the beach, but you’ll be able to walk to shops, restaurants and free trolley stops! Enjoy the private heated pool too.
Beach Escape is three blocks from Gulf beaches and also centrally located to Anna Maria Island activities and attractions. This 3 bedroom, 3 bath rental offers accommodations for up to 8 guests. Inside you’ll find an updated style with the cool blues and whites characteristic of Mediterranean decor. Enjoy the heated pool and spa, or open air balconies at this fantastic Anna Maria Island beach rental!
Located in Anna Maria, Blue Waters is a platinum rated rental on direct canal front. This 4 bedroom, 4 bath home sleeps 8 guests, and is a few blocks from coveted Anna Maria gulf beaches. You’ll find luxury amenities including a large heated pool and spa, boat dock and a lovely Mediterranean style. You’ll truly love this one of a kind destination.
Casa Sierra Rentals
Casa Sierra is a small 4 unit condo complex just a short two blocks from gulf beaches. These great Mediterranean style condos offer 2 bedrooms and 2 baths with accommodations for up to 6 guests. These rentals are relaxed, however, they do have all the great amenities that come with their gold rating. Enjoy the community heated pool along with a fabulous location too. Casa Sierra Unit 205 A, Unit 205 B, Unit 203 A.
The L’Plage complex is on direct gulf front in Holmes Beach. This luxury condo offers everything you’ll need for the perfect Mediterranean style holiday. Enjoy the community heated pool and spa just steps from the powder white sands of the Gulf of Mexico. Inside this unit you’ll find 3 bedrooms and 3 baths with room for up to 8 guests too!
Beach House on 5th is a great spot for up to 10 guests! This 3 bedroom 3 bath rental is less than 3 blocks to gulf beaches, shopping, dining and free trolley stops too. You’ll love the heated pool and the fun coastal decor in this Mediterranean style home.
You’ll enjoy direct gulf front views when you spend a holiday at Vista Grande. This lovely platinum rated villa sleeps 6 guests with 3 bedrooms and 3 bathrooms. Not only does this beach rental have million dollar views, but also luxurious amenities fit for a Mediterranean style vacation.
Perfect for a family getaway, The Oasis has accommodations for up to 6 guests with 3 bedrooms and 3 bathrooms. You’ll be 3 blocks from pristine Gulf of Mexico beaches, and centrally located on Anna Maria Island. Enjoy the heated pool during your stay!
The La Casa Costiera is a gorgeous luxury condo complex right on the Gulf of Mexico. Here you’ll find many well-appointed rentals to pick from. These units sleep 6 or 8 guests, and each has unique tropical decor. They have 3 bedrooms and either 2, 2.5 or 3 bathroom. Enjoy the heated pool and spa or relax all day long on the beach.
This canal front Anna Maria rental is just a short walk to Tampa Bay beaches. You’ll love the fantastic style and amenities at Cayman Bay. Sleep up to 8 guests with 4 bedrooms and 4 bathrooms. Each of the bedrooms at this home have a great luxury feel. Enjoy the beautiful backyard with a heated pool and spa. Dock your boat in the canal too!
Enjoy the beach on a budget when you travel to sunny Anna Maria Island! We have some of the best powder fine coastline on the gulf coast, and the best deals too! Find affordable accommodations, cheap eats, and tons of free activities to make your vacation fun and easy on the wallet.
Beach on a Budget
Anna Maria Island is a fantastic place to beach on a budget for any size group and all ages too. You will find a large selection of economical accommodations with Island Real Estate.
Below is our list of money saving ideas to try out on your next Anna Maria Island beach vacation. Not only do we have tips for finding affordable accommodations, but a guide to assist you in an authentic Florida vacation.
Finding Affordable Anna Maria Island Beach Rentals
Travel in the off season
When looking for the best rates on accommodations you should avoid traveling in the high season. Off season travel yields the best deals on accommodations, and this is especially true of Anna Maria Island. The peak busy season on the island is March. For off season deals book your stay August through October or January.
How to find online specials
Once you pick a time of year to visit look for specials at IslandReal.com. Each individual beach rental will offer different types of specials through the year in both high and low season. Those booking last minute stays can find great deals on beach rentals that are looking to fill dates. Also check for seasonal sales. Typically promotions you come across will not apply to big holiday weeks.
Sign up to be added to the Island Real Estate news letter list. We are always sending out promotions and specials via email!
Island Real Estate regularly offers promotions and specials through our social media too! Be sure to find us on your favorite social media platform for regular updates on deals. Facebook, Twitter, Instagram, Pinterest.
Eat like a local!
Locals places are not only the best way to save money, but they are the most authentic version local culture. Sure, Anna Maria Island has tons of places that attract tourists for a good time. However, there are a few places you just may overlook.
Mr. Bones BBQ is a great locals spot with large portions and reasonable prices. Not only do they have the areas best BBQ, but they have vegan options, burgers, and a large beer selection. You’ll find just something for just about everyone when you visit Mr.Bones BBQ in Holmes Beach.
Starfish and Tide Tables restaurants are owned by the same fishing family out of Cortez. You only have to ride just over the bridge into Cortez Fishing Village for the best seafood on the gulf coast. Both of these restaurants are the spot for fresh seafood that won’t cost you too much. Be sure to bring cash when visiting Starfish.
Danny’s Pizza is also just off island. Head over the Manatee bridge into Bradenton and you’ll find the best New York style pizza the area has to offer, The prices are always reasonable, the service is great, and the food is consistently a crowd pleaser.
Poppo’s Taqueria is on the north end of the island in the city of Anna Maria’s Pine Avenue. The portions here are huge, the food is conscientiously sourced and prices are fair for the quality. Poppo’s is some of the best Tex-Mex style food you’ll find. One taco and you’ll be hooked like the island locals.
Duffy’s Burgers has the best the island can offer. They have been in business for years. The locals can tell you this authentic burger and beer joint has a reputation. Must bring cash too!
Dine in for a Penny Pincher Beach vacation
One of the nice things about getting an Anna Maria Island beach rental is the benefit of a full kitchen. All of the Island Real Estate beach rentals come with fully equipped kitchens to accommodate all your basic needs. If you are looking to dine on a budget then prepare meals at your rental. Many of the beach rentals you’ll find will even come with an outdoor grill to make cooking easy while enjoying the beautiful tropical climates. Check out the information here for cooking in a beach rental.
A great way to save money on vacation is to avoid paying for transportation when possible.
Anna Maria Island has a free trolley to help. The trolley runs almost the entire length of the island from morning until night. This is a great way to get around for free!
Additionally, there are many local transportation services that are free, but accept tips only. You can set an appointment or flag down services such as The Monkey Bus with little cost.
Rent a bike
Occasionally beach rentals homes may be equipped with beach bikes, but you can rent one for very little. This is a great way to get around the island for very little money. Anna Maria Island also has bike paths. This is a great way to sight see, stay active and do it all on a budget.
Anna Maria Island is full of free or inexpensive activities! While the beach is always free, there are many other areas to explore too!
Anna Maria Island has plenty of beaches to visit, and it won’t cost you a dime! There are over seven miles of coastline, so you can find just the perfect beach spot. Additionally, parking is free at just about any beach you can find. As long as you follow all parking signs, parking is free.
Anna Maria Island has interesting local wildlife, and all our local parks and preservers are free! Check out Leffis Key on the south end of Anna Maria Island or Robinson Preserve in Bradenton. Nearby Perico Island offers Neal Preserve, Perico Preserve and an access to Robinson Preserve. This area is fantastic for exploring both wetlands and upland Florida environments. Best of all, it’s free!
If you are looking to book a fishing charter this is a great way to pay for both the cost of a meal and an excursion around island waters. Nothing tastes better than fresh fish you caught and cooked!
Learn about Anna Maria Island history at the Historical Society. This free activity will give you some insight into how the island came to be, and who lived here. Find out how Fig Newtons built the island! See like the old city jail, and much more.
When looking for an affordable island vacation be sure to come prepared. While Anna Maria Island is not an expensive destination, there are some things you can avoid buying to save money. Bring all the clothes, toiletries and accessories you’ll need with you. This is especially true if you are traveling by car. Buying a bathing suite and touristy accessories on island can drive your spending up. Think about the things you can fit in your travel bag or car before you come. You don’t want to spend extra money on things you left at home.
Enjoy the Beach on a Budget during your next Anna Maria Island vacation in Florida!
An Anna Maria Island Winter is absolutely wonderful! While temperatures vary, typically you won’t see day time cold weather below 50 degrees Fahrenheit during island winters.
Anna Maria Island Winter Fun Activities
Follow our list of cold weather activities and you’re sure to have a great time for your Anna Maria Island Winter vacation!
Sand Angel and Sand Men too!
We don’t have snow in Florida, but we do have sand. Tons of it! On Anna Maria Island there is over seven miles of powder fine sand coastline ready for you to play in. Instead of the traditional snow angels and snow men try your hand at a sand man or sand angel.
Dining and Shopping
Naturally, when visiting even warm winter climates, you’ll want to have indoor activities. Luckily, Anna Maria Island has tons of great dining and shopping spots! You’ll find shopping and dining spots peppered across the island, but there are a few hubs to keep in mind. Pine Avenue in the City of Anna Maria offers great boutiques and restaurants. The Central city of Holmes Beach has a commercial district at the corner of Marina and Gulf Drive. Then a second spot on East Bay Drive and Manatee Avenue. Bradenton Beach, the southern island city, offers great shopping and dining on Bridge Street.
Since there are fewer people on the beach in the winter, your chances of finding the best seashells increases. Beach combing is a relaxing pass time. Bundle up with a thick sweater and head out to the beach for some great winter shelling!
Hot Chocolate with an Island Twist
Cold winter months were made for curling up with a blanket and a cup of hot chocolate! This is a great way to relax at an Anna Maria Island beach rental during the cold months. Try this recipe for Toasted Coconut Hot Chocolate and you’ll have an island twist for an old standby.
Winter is a lovely time for kayak trips around Anna Maria Island. Since the Gulf may be too cold for your liking, you can still get out and not get wet with a kayak. Often, during winter, you will find the Gulf is flat like glass. This makes kayaking fun, safe and relaxing. You could also head over to the Intracoastal side of the island to find Mangroves and diverse wildlife.
Dolphins are not hard to find around Anna Maria Island. This is especially true when you book a boat tour. Many of the local charter captains know where to find pods of Dolphins jumping and playing around the island. A trip to the island isn’t complete without spotting a dolphin.
Fishing is great anytime of year in Florida, and winter is no exception! Head to a pier, or book a fishing charter. Either way you’re sure to catch something good!
Winter Beach Rentals
While visiting Anna Maria Island in the summer is fun, the cooler months still bring a great opportunity to visit the gulf coast. You will find great economy options on beach rentals during the winter. Especially during January, rental prices are at some of their lowest! You won’t have to break the bank to escape the winter snow and ice.
Salt a Margarita instead of your driveway!
Don’t spend winter salting your driveway, come to Anna Maria Island and salt a Margarita instead!
A New Years Anna Maria Island style is full of relaxation and fun. What’s a better way to transition from one year to the next than doing it on the beach? Here is our suggestions of fun things to do on New Years Eve and Day on Anna Maria Island!
New Years Anna Maria Island
Anna Maria Island might be a little chilly in the winter, but it sure beats spending winter up north. Even with the cooler weather, there’s plenty of things to do on Anna Maria Island around New Years. Typically new years on the island is very laid back. You won’t find lots of loud crazy shenanigans. People enjoy time with family and friends while relaxing in paradise.
New Years Eve
Sunset. When visiting the island on New Years Eve, be sure to catch the last sunset of the year. Anna Maria Island always has a beautiful sunset, and the last one of the year is always special.
Go for a swim! If you visit an Anna Maria Island beach rental with a heated pool or spa, you can totally swim in January. How many of your northern friends can do that? If you are from the north, you may even be brave enough to jump in the gulf!
Party. Traditionally, people love a party on New Years Eve. While the island doesn’t have a local ball drop, there are many places to celebrate. Just about all island restaurants and bars are open on New Years Eve. Even better, the free trolley passes by almost all of them! You can have fun, and drink responsibly too! Many of the restaurants will close before 11pm, but all the bars will be open until midnight or 2pm.
Eat. If you plan on staying in for New Years Eve try out some fun tropical recipes for an island twist on a New Years Eve party! Instead of a traditional champagne toast, try out pineapple mimosas. These Hawaiian sliders are a great twist on a pulled pork sandwich, and make great finger food for a party. Grouper and Shrimp are both caught locally. Get some local seafood and make seafood tacos!
New Years Day
Sandbar Jazz Brunch.Sunday Jazz Brunches at the Sandbar Restaurant have become very popular on Anna Maria Island. This year January 1st falls on a Sunday, and therefore, coincides with this event. Enjoy a special menu while listening to local Jazz performers in paradise. This is a fantastic way to start the new year!
Beach Photos. Start the new year off with pictures on the beach! Gather all your family and friends and get a great shot to remember the day.
Try a new Island Activity. Begin the new year with an island style activity you never tried before. A new year is for new experiences. See the Ultimate Anna Maria Island Bucket List for inspiration and activities that you’ve never tried before.
New Years Anna Maria Island Beach Rentals
Anna Maria Island beach rentals are a great option for any size group spending New Years in paradise! Book your stay with Island Real Estate, and find the perfect accommodations for you.
Beach Comber is a great direct gulf front beach rental. Enjoy accommodations for up to 6 guests with 2 bedrooms.
Bay View Inn 201 sleeps 4 guests with 1 bedroom. You’ll love this location just a couple blocks from gulf beaches, dining, shopping and trolley stops.
Sea Palm Cottage is a charming rental just a block from gulf beaches in Holmes Beach. Sleep up to 6 guests with 3 bedrooms and 2 baths.
Runaway Bay 272 sleeps 6 guests with 2 bedrooms. This condo rental is just across Gulf Drive from the beach. Enjoy the heated community pool and Bay viewing dock.
This is the ultimate Anna Maria Island Bucket List! There are tons of great activities to enjoy during your visit, however, there are some must dos. Follow this great list and you’ll be sure to have a blast on Anna Maria Island!
The Ultimate Anna Maria Island Bucket List
Visit an Anna Maria Island vacation rental on the beach. – This is the best way to visit Anna Maria Island!
Eat a burger from both Duffy’s and Skinny’s. Locals are divided about the best burger on island, so find out for yourself.
An Anna Maria Island Thanksgiving is a great way to spend the holiday with friends and family by the beach! Once you arrive, enjoy a relaxed location with family friendly activities and accommodations. You’re sure to love filling up on a turkey feast in tropical paradise.
Anna Maria Island Thanksgiving Guide
We have put together a list of everything you need to know about spending Thanksgiving on Anna Maria Island. Get ready for a family gathering you won’t soon forget with this helpful guide!
Anna Maria Island Beach Rentals and Accommodations
Island holiday rentals fill up fast on Anna Maria Island, but Island Real Estate still has availability! Whether you are looking to sleep a couple or even a large group, we have openings.
Bay View Inn 102
This Bradenton Beach Condo sleeps up to 4 guests with 1 bedroom. You’ll be just a couple blocks from gulf beaches, shopping, dining and free trolley stops!
Sunfish sleeps 4 guests with 2 bedrooms. This Holmes Beach duplex rental has a shared heated pool and is less than a block to gulf beaches.
La Casa O’Bar
A luxury beach front rental, La Casa O’Bar sleeps 6 guests with 3 bedrooms. Enjoy glimpses of the gulf and the heated community pool too.
This Holmes Beach rental sleeps 8 with 4 bedrooms. Enjoy a private heated pool and spa, and tons of kitchen space for making Thanksgiving dinner.
Just two blocks from gulf beaches, Sunset Glow sleeps 10 guests with 5 bedrooms. This platinum rated rental offers a heated pool and spa along with a gorgeous kitchen.
Thanksgiving Restaurant Openings
There are many restaurants open for Thanksgiving on and around Anna Maria Island. Here is our list of the five places to dine out for Thanksgiving on Anna Maria Island. These are not the only local options, but rather, just the places open on island.
There are some fun things to do during an Anna Maria Island Thanksgiving. Keep your friends and family entertained during the day with activities!
Beach It! A Thanksgiving on Anna Maria Island isn’t complete without a trip to the beach. The water might be a tad crisp, but the weather is sure to be warm enough for beach time.
Bike Rides are a great activity for the family. Enjoy sightseeing while you burn off all that food you ate!
Nature walks are a lovely and relaxing Thanksgiving activity. Head over to Leffis Key or Robinson Preserve for beautiful wildlife viewing. Both these preserves are open dusk until dawn.
Trolley Hop. Ride around the island with the free trolley. This is the best way to explore those hard to find beach accesses of north end.
Pier Fishing. Head over to one of the island’s three public piers and bring your fishing pole too! All public piers have a blanket fishing license, so even visitors can catch their own island style Thanksgiving dinner. Fish off the Bradenton Beach city pier at the end of Bridge Street. Also find the Rod and Reel Pier and the Anna Maria City Pier located near Pine Avenue.
The license free fishing days are a great opportunity for Floridians and visitors to experience a day on the water. These free days apply to onshore, pier and boat fishing. These fishing holidays only apply to recreational fishing, and do not cover commercial fishing.
Additionally, seasons, size limits and bag limits do still apply. When fishing during these times be sure you know what you may and may not keep! The saltwater dates do also cover any type of recreational harvest, in season, including scalloping, lobstering and many other angling activities.
Enjoy license free fishing days on Anna Maria Island on your next visit!
Fishing from Anna Maria Island vacation rentals
Honeywood House is a great Anna Maria Island vacation rental for a little dock fishing! This canal front home has a dock for relaxing while doing a little fishing. If you bring a boat on vacation you can dock it here too! This canal takes you out to Bimini Bay and Tampa Bay for great fishing trips! Book your stay at Honeywood House today!
The Cortez Stone Crab Festival is back in it’s fifth year of tasty fresh seafood and family fun. Join in this claw cracking good time November 5th and 6th in the old Fishing Village of Cortez.
Cortez Stone Crab Festival
Hosted by Swordfish Grill and Tiki Bar, the Stone Crab Festival is the best time to enjoy this local delicacy. Find the festivities in the fishing village at 4628, 119th Street West. The event starts at 9am and ends at 6pm on Saturday and Sunday.
In addition to Stone Crabs, there will be live music, kids activities, arts and crafts vendors, and a beer tent. There will also be a large tent for shade, and you may bring your own folding chairs.
Parking will be available at 116th Street at the F.I.S.H. Preserve with shuttles going back and forth through both days.
Live music will be happening on three different stages around the event.
For Stone Crab claws that are so fresh they never travel by land, head over to the Cortez Stone Crab Festival!
Historic Bridge Street is a quaint strip of restaurants and shops on the south end of Anna Maria Island. Once the site of the first bridge connecting the island to mainland Bradenton, Bridge Street is still a special place. Check out our list of things to know about Bridge Street.
Historic Bridge Street – Bradenton Beach City Pier
At the very end of Bridge Street you’ll find the Bradenton Beach city pier. Here you’ll enjoy views of Sarasota Bay as you walk along the site of the original bridge to the island. After many updates the pier still stands today. Now you can find great fishing, a bait shop and the Anna Maria Oyster Bar restaurant.
There are a variety of places to dine on Bridge Street including casual, high end and breakfast too. Enjoy The Blue Marlin, Island Creperie, and the Bridge Street Bistro to name a few. For the nightlife scene you can visit Bridge Tender Inn, Island Time Bar and Grill, or even the Drift Inn. You’ll find these places open a little later than the average island establishment.
Happenings and Events
Throughout the year you’ll find different things to do on Bridge Street. The local Merchants host several events such as Christmas on Bridge Street, pubic art shops and the occasional market.
Nearby Accommodations and Beach Rentals
There are many great Anna Maria Island Beach rentals near Bridge Street. You’ll find cottages, condos and single family homes available in Bradenton Beach.
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How To Find Island Real Estate
Office LocationsIsland Real Estate 6101 Marina Drive Holmes Beach, FL 34217