Anna Maria Island Vacation Rentals Guide

South West FL / Anna Maria Island


Found on Florida's Southwest Gulf coast just south of Clearwater and north of Sarasota, Anna Maria Island is the perfect vacation spot for a quiet Old-Time Florida holiday. 

Known for their 7-miles of pristine award-winning, white, sandy beaches, fishing, boating and an abundance of outdoor sporting activities from kayaking to jet-surfing. As well as their small Key West style villages dotting the island creating a small town feel. 

There are tons of things to do on Anna Maria Island and the Islanders host a myriad of great events throughout the year, fun festivals and events to partake in while you visit this little island in the sun. This Florida gem will quickly have you addicted and keep you coming back year after year to explore what you missed. With the pride of ownership, Anna Maria Island is home to some of the most beautiful vacation rentals in the entire state.


Anna Maria

Anna Maria is a city located on the northernmost tip of the island in Manatee County, Florida. The population is a little over 1,800. Known for its picturesque Key West-style main street on Pine Avenue and its historic 100+ year-old fishing pier.  Walkable from east to west and north to south it's the perfect backdrop for island living. It's the perfect place for couples, snowbirds, and families to relax and enjoy a sleepy small town atmosphere.

 The perfect place for couples, snowbirds, and families to relax and enjoy a sleepy small town atmosphere.

Holmes Beach

Holmes Beach is a city located in the center of the island in Manatee County, Florida. The population is close to 5,100. Holmes Beach is known for being the heart of the island, supplying the island with a grocery store, pharmacy, many restaurants, and stores. It's the perfect place for active couples, snowbirds, and families with an abundance of volleyball nets and beach activities provided at the County's Public Beach.

Bradenton Beach

Bradenton Beach is a city located on the southernmost tip of the island in Manatee County, Florida. The population is a little over 1,500. Known for its beautiful Bridge Street Pier it has a down to earth & lively vibe. Bridge Street has many shops and restaurants to enjoy. Coquina Beach has an incredibly scenic bike path of 1.5 miles to enjoy on the Gulf. It's the perfect place for couples and snowbirds. This city has the most condos and townhomes offered on the island.


  • There are six award-winning beaches on Anna Maria Island and there is something for everyone from toddlers to octogenarians. You'll find the perfect spot for you on the pristine sandy beaches here.
  • Don’t be surprised to see golf carts instead of cars on this quaint little island in the sun. A super fun way to zip around the island with the salty air blowing in your hair.
  • A Free Trolley service runs the entire length of the island and is a hop on hop off service.
  • Sea Turtles are sacred and protected on this island. Hundreds of turtles return to nest each year. 
  • There are only 3 bridges to the island and speed limits are below 35 mph. Expect slow traffic during the spring, summer seasons and holidays.
  • This is an extremely quiet and sleepy island where most restaurants and bars close up by 10 pm. 
  • Best Suited for outdoorsy types, such as active families, couples, and snowbirds.


Anna Maria Island is a special place, perfectly suited for outdoor living. Here’s a handy list of things to do on the island to help you find out if it’s the perfect fit for your next vacation. 

  • 6 award-winning beaches
  • surfing, skim boarding, body boarding
  • fishing (beach, boat and pier fishing)
  • boating
  • kayaking
  • SUP
  • Kiteboarding
  • jet-surfing
  • biking
  • mini putting
  • boutique shopping
  • great unique restaurants


Search, find and book your Anna Maria Island, Florida vacation rental on Florida Rental By Owners website. Exclusively for travelers wishing to communicate and book directly with the owner. There are no traveler fees for using Florida Rental By Owners website. Owners are verified for ownership. All transactions occur directly with the owner. Read reviews and guest experiences to ensure your vacation rental will meet your goals.

Do you have questions about the Anna Maria Island area? 

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Traveling to Anna Maria Island

There is an abundance of airports to choose from all within 2 hours of Anna Maria Island. Whether you live in the United States, Canada, Europe and beyond you are sure to find a final destination close by.

Sarasota - Bradenton International Airport - (SRQ)

Sarasota - Bradenton International Airport is the closest airport to Anna Maria Island. It is 17 miles (27 km) away from Anna Maria Island. Travel time is approximately 35 minutes. This airport is serviced by seven major carriers, two of them Canadian. Air Canada & West Jet. U.S. carriers are United, American, Delta, Elite, and Jet Blue Flights are not offered year round since it is considered a tourist destination check with each carrier.

St. Pete - Clearwater Airport - (PIE)

St. Pete - Clearwater Airport is located in mid-way between Clearwater and St. Petersburg. It is 45 miles (72.3 km) away from Anna Maria Island. It usually takes 55 minutes to an hour to travel this route. This route has a toll. It is a destination for low-cost carriers. The main airline carrier is Allegiant Air. PIE is less busy than Tampa International Airport and is frequently used by pilots of private planes and executive jets.

Tampa International Airport - (TPA)

Tampa International Airport is 52.6 miles (85 km) away from Anna Maria Island. This route has a toll and usually takes 1 hour and 15 minutes to travel. This airport is served by over 20 major airline carriers.

Southwest Florida International Airport - Fort Myers - (RSW)

The Southwest Florida International Airport services many airline carriers notably Southwest, Delta, American, Spirit and Jet Blue. It is located 111 miles (179 km) away from Anna Maria Island which takes approximately 1 hour and 50 minutes to travel.

Orlando International Airport - (MCO)

Orlando International Airport is 126 miles (203 km) away from Anna Maria Island. Travel time is approximately 2 hours and 10 minutes. Be careful of traffic in Orlando, it is a busy city but is also a nice stop for shopping and of course Disney and other amusement parks before arriving on the island. It also has a hotel on site for late night arrivals or early departures.

This airport is the second busiest in the state of Florida and services 39 airline carriers. in addition to U.S. and Canadian options, it is the best option for European flights.

Transportation on Anna Maria Island

We've compiled a handy list of transportation options to get you to Anna Maria Island from the airports. Anna Maria Island is a walking community meaning once you are on the island you can pretty much walk everywhere or take many car-free transport options to get you where you need to go.

Dolphin Limousine


The Monkey Bus

The Island Beach Monkey Bus is just one of the modes of transportation this fun company has. You’ll see their golf carts zipping around the island as well. Whether you need a quick ride somewhere on the island, or need golf cart or bus transportation for an event, like a wedding, or to an event, like a baseball or hockey game, this is the company who can help. Contact  ISLAND BEACH MONKEYS 941-565-6542

Golf Carts, Sports Rentals, Bikes and More!

Anna Maria Island is very Golf Cart Friendly. It’s a fun way to get around in our warm climate. There are several businesses that rent Golf Carts by the day or by the week. There are also a ton of other fun things to try like biking, kayaking, paddle boarding, and so much more. You can rent from our preferred vendor at FUN AND MORE RENTALS. They all deliver to your rental and pickup too. Head to their website to see their full assortment.  FUN AND MORE RENTALS

Free Trolley

There is a free Trolley service on Anna Maria Island. It is super convenient to travel the island from one end to the other from 6:00 AM until 10:00 PM. Go touring, pick up your groceries or go out to dinner and have a drink.

AMI Water Shuttle

Island Pearl Excursions offers three vessels Island Pearl, Now and Then, and Island Girl operating from Cortez on the North end of Sarasota Bay! All vessels depart from the Seafood Shack in Cortez. Take a tour or shuttle across the bay or charter your own private boat for an epic excursion. Contact   ISLAND PEARL EXCURSIONS  today.

Anna Maria Island Monthly Average Weather Chart


What types of property can I rent in Anna Maria Island, Florida?

Florida Rental By Owners is full of a wide variety of vacation rentals in Anna Maria Island, Florida including condos, cottages, town-homes, duplexes, villas, holiday and private homes. Our 2018 property selection is filled many properties in Anna Maria Island. We recommend selecting a property based on your needs such as proximity to beach areas, waterfront docks, parking, wheelchair accessible, nearby attractions, and whether or not the property is pet-friendly or boat-friendly.

Should I rent a Cottage in Anna Maria Island?

Yes, if a cottage is right for you! Most cottages in Anna Maria Island offer amazing beachfront views! Some include free beach gear and countless amenities such as pools, hot tubs, backyard beaches, tiki huts, fitness rooms, and ping pong tables. If this is what you are looking for, then you should rent a cottage in Anna Maria Island.

Should I rent a Condo in Anna Maria Island?

Of course! Anna Maria Island accommodations include condos which often offer unique amenities and the perfect space rather than an Anna Maria Island cottage or large private home for example. House rentals are often great for family vacations, larger groups or those who prefer having an entire house and outdoor property to themselves.

Can I rent a pet-friendly rental in Anna Maria Island?

Yes! We love our pets and we are sure you do too! has many pet-friendly rentals in Anna Maria Island. You can use our search feature to narrow down our Anna Maria Island rental properties to just show those that are pet-friendly.

Can I rent a boat-friendly rental in Anna Maria Island?

Anna Maria Island is the perfect place to bring your boat or rent one from a local vendor! (Florida Rental By Owners) has many boat-friendly rentals in Anna Maria Island. Use our search feature to narrow down our Anna Maria Island rental properties to just show those that are boat-friendly.

Is Anna Maria Island a good place for Snowbirds looking for a monthly rental?

Yes, there are many homes and condos that rent monthly on Anna Maria Island that would be perfect for longer stay guests. Also, look just off the island to nearby Perico Key Island.

Will I pay any fees to book a property on Florida Rental By Owners?

Never! We never charge any fees to book a property on Florida Rental By Owners. And we never take a commission from an owner.  If you are looking for VRBO or Airbnb type rental or lodging accommodation why pay the extra fees? Use! We put you in direct contact with the owner or manager of the property or cottage rental in Anna Maria Island so you always get the best price.

Start looking for your Anna Maria Island Vacation Rental

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