Anna Maria Island Vacation Rentals

Absolute Anna Maria
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
WELCOME TO OUR FAMILY FRIENDLY CONDOMINIUM
From $131 /Night
Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
The Blue Heron is a beautiful 4 bedroom 3.5 bath brand new luxury home on Anna Maria Island for rent.
From $480 /Night
Edge of Paradise at Margaritaville - 5 Night Min - monthly's wanted
South West FL > Anna Maria Island
Condo , Bedroom(s): 3 , Sleeps: 8
Luxe Condo I Resort Amenities I Near Anna Maria Island I Margaritaville
From $170 /Night
AMI Waterfront Bradenton Beach Condo w Pool!
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Watch sunrise over the bay and walk across the street to enjoy the beach. Restaurants, bars and shopping all within walking distance!
From $890 /Week
Anna Maria Island Paradise❤️Close to beach, shops&restaurants, heated pool, private lanai!
OFFER
Anna Maria Island Paradise❤️Close to beach, shops&restaurants, heated pool, private lanai!
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Book a relaxing vacation at our condo, situated in a private complex on the beautiful Anna Maria Island, only a short walk to the beach, shops and restaurants!
From $100 /Night

OFFER Last Minute Deal - $1,105 per week ALL IN (including all taxes and fees!)

Special offer period: Oct 24, 2020 - Nov 28, 2020

Gorgeous AMI Villa with private pool & just steps to the beach!
OFFER
Gorgeous AMI Villa with private pool & just steps to the beach!
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 3 , Sleeps: 6
Welcome to AMI Villa! When you come to Anna Maria Island, make this charming Mediterranean 3 bed & 3 bath villa with a private pool your home away from home!
From $225 /Night

OFFER Last Minute Deals- November 1-7 $1,900 and November 14-21 $2,160! All taxes and fees are included!

Special offer period: Nov 1, 2020 - Nov 21, 2020

Anna Belle - Waterfront Luxury Home: North End wDock, Pool, Spa, Screened Lanai, Free WiFi
OFFER
Anna Belle - Waterfront Luxury Home: North End wDock, Pool, Spa, Screened Lanai, Free WiFi
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 8
Ground level living, 3 bedrooms, 2 baths, sleeps 8. Private Home with Waterfront Dock, Pool, Hot Tub, Wifi
From $300 /Night

OFFER November Escape - $300/per Night, 4 Night Minimum

Special offer period: Nov 7, 2020 - Nov 21, 2020

Cozy Cabana West
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 2 , Sleeps: 6
2Bed/2Bath, Private Heated Pool!
From $170 /Night
Oct 3 - Oct 10 Deal! - Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 10
Sirenia Beach House ~ Beach Resort Style Luxury - Waterfront - Dock - Htd Pool - Spa - Backyard Beach - Tiki Hut - Hammock and more!
From $233 /Night
Sirenia Cove - Htd Pool Waterfront Dock Ping Pong Outdoor Bar Backyard Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 10
Sirenia Cove is the perfect vacation home to nature lovers. Located directly on the waterfront, you are perched on a prime location to enjoy everything.
From $1,799 /Week
Sirenia By The Sea - Waterfront Pool Hot Tub Dock Sauna - Steps to the Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 5 , Sleeps: 12
Picture yourself vacationing in a huge 5 Bedroom luxurious tropical villa, the perfect vacation rental for large groups on beautiful Anna Maria Island.
From $1,999 /Week
Blue Turtle Cottage Anna Maria Island Available For Christmas & New Years!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Blue Turtle Cottage Anna Maria Island has a sparkling private pool and is just steps to the white sand beach!
From $256 /Night
Beautiful, Gulf-Front Home --Halcyon House
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
As seen in Coastal Living Magazine, this is a 3 bedroom beachfront home on desirable Bean Point with with direct access to Bean Point Beach.
From $750 /Night
Bay Watch Bungalow
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
Bay Watch Bungalow: Water Views from Every Room & Upgrades Galore
From $118 /Night
Tropical Setting and Heated Lagoon Style Pool at "Your Own Oasis"
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Your Own Oasis is a newer, 3bed/2bath Retreat with a Private Lagoon Style Pool, close to both Bay and Beach and the free trolley stop is just one block away!
From $157 /Night
Renovated 22 Cottage North End-Steps to Beach Tropical LandscapingHeated Jetted Pool
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 2 , Sleeps: 4
SURF’S UP has been completely and lovingly renovated from top to bottom and is gorgeously decorated!
From $291 /Night
22 North End Beach House near Bean Point Beach!!
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 2 , Sleeps: 4
Located on the desirable North end of Anna Maria Island just steps away from the famous Bean Point Beach, Rod N Reel Pier and Bayfront Park!
From $269 /Night
The Anna Maria Island Beach Sands 203
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
The Anna Maria Island Beach Retreat, 2 bedrooms, 1 bathroom, sleeps 6 maximum
From $152 /Night
Anna Maria Island Retreat
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $153 /Night
Playa Encantada, Steps to the Beach
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 4
Located in the sought after complex of Playa Encantada; Shell Game is a tropical beach front community on the white sandy beaches of Anna Maria Island!
From $156 /Night
North End Luxury Beach Cottage STEPS TO THE BEACH Heated Pool and Outdoor Living Area
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 2 , Sleeps: 4
Seahorse Cottage is one of our most popular properties located on the desirable North End of Anna Maria with a Heated Pool and Outdoor Living Area
From $291 /Night
The Anna Maria Island Beach Castaway 1
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $101 /Night
PRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 4
LUXURY CONDO 2 Bed 2 Bath * SEE SUNSET FROM LANAI * WALK TO SHOPS/RESTAURANTS
From $171 /Night
The Anna Maria Island Beach Paradise 10
South West FL > Anna Maria Island
Condo , Bedroom(s): 1 , Sleeps: 2
Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach.
From $143 /Night
The Anna Maria Island Beach View 209
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $121 /Night

Is Anna Maria Island a good place to vacation to?

About 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.

What cities are found on Anna Maria Island?

Cities of Anna Maria Island, Florida

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.

What are Popular Things to Do on Anna Maria Island?

Highlights and Area Attractions of Anna Maria 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 and the island Shorebird and Turtle Group offer lectures and nest excavations to educate visitors.
  • Keep your eyes out for colorful pink Roseate Spoonbills, bald eagles, osprey, brown and white pelicans, egrets, wild green parrots, and snowy plovers that call Anna Maria Island home.
  • 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.

Things To Do on Anna Maria Island

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

  • 6 award-winning beaches, don't miss Bean Point an idyllic natural spot on the north end of the island or Coquina Beach for the 4 mile-long bike trail
  • surfing, skimboarding, bodyboarding
  • fishing (beach, boat and pier fishing)
  • boating along the inter-coastal waterway, to nearby Egmont Key, Tampa Bay or out into the Gulf of Mexico all the way up and down the coast
  • kayaking in Bimini Bay, Robinson Preserve, the inter-coastal waterway where calmer waters flow
  • SUP in Bimini Bay, Robinson Preserve, the inter-coastal waterway where calmer waters flow
  • Kiteboarding
  • jet-surfing
  • biking
  • mini putting
  • boutique shopping in the 3 villages Anna Maria, Holmes Beach, and Bradenton Beach will garner you some unique coastal finds.
  • great unique restaurants

What do I need to know to rent a vacation home rental on Anna Maria Island?

Statistics about Anna Maria Island

Use the search filters on Florida Rental By Owners website to look for accommodations meeting your criteria. There are currently over 147 properties in Anna Maria Island listed for rent on Florida Rental By Owners (FlaRBO). There are 41 condos advertised out of 147 properties. The majority of properties listed have heated pools - 123 rentals which make this an ideal year-round destination. Many winter travelers are looking for long-term rental options, choosing the long term suitability filter renders 55 rental options for snowbirds. People loving traveling with their furry family members. On Anna Maria Island there are over 49 rentals where you can bring your pet along on holiday.

Vacation Rental Price information pertaining to Anna Maria Island

Currently, prices range from 75$ per night and $700 per week during the low season which typically runs from the end of August to the month of November. January is also considered a low season month. You can expect to pay the highest rates during the high-season running from February through to the first or second week of April where prices of larger homes can cost over $1,000 per night. The summer months, June and July are also favorite times for local travelers from the state of Florida, Georgia, and South Carolina to escape to the coast for cooler breezes and boating. There are 16 vacation rentals with docks available on Anna Maria Island.

Accommodation Types on Anna Maria Island, Florida

There is an abundance of vacation rental dwelling types, the majority ranging from condos to private homes: 

  • 70 rentals are listed as "house" rentals, accounting for 47.6% of the housing types
  • 41 rentals are listed as "condo" rentals, are another popular rental type accounting for 27.9% of the short term rental housing types
  • 10 rentals are listed as "townhouses"
  • 4 rentals are listed as "bungalows"

Anna Maria Island FAQ's

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. The FlaRBO property selection is filled with 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 Beach Cottage on 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 on 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. Anna Maria condo rentals are perfect for smaller families and couples. 

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

Yes! We love our pets and we are sure you do too! FLARBO.com has many pet-friendly rentals on 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 on Anna Maria Island?

Anna Maria Island is the perfect place to bring your boat or rent one from a local vendor! FLARBO.com (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 vacation rental?

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

When is the Best Time to Visit Anna Maria Island?

With the incredible weather patterns year-round, any time and month of the year are good times to visit Anna Maria. Peak seasons follow the school year and holiday patterns with peaks from February to mid-April and the summer months of June and July are great times for the whole family to visit. Off-season from mid-August to the third week in November offers the least expensive and quietest times of the year to rent a property on the island. The Off-season in the Fall does offer an abundance of festivals and events such as Bayfest, Symphony on the Sand, Stone Crab Festivals, and Arts and Craft shows which are always fun to attend.

What is the average monthly Weather Temperature for Anna Maria Island?

Looking at our average weather climate chart above. July and August are the warmest months on Anna Maria Island with average maximum temperatures of 93°F highs. Cooler temperatures prevail in the month of February, where minimum average temperatures at night average 52° lows. The wet season occurs in August. Most people travel to Anna Maria Island for the beaches and the Gulf of Mexico temperatures range in the hottest months of May, June, July, August, and September between 82°F to a steamy 87°F

What is the crime rate of the cities on Anna Maria Island?

According to area-vibes.com, crime rates in each city are the following:

Anna MariaThe crime rate in Anna Maria is 85% lower than the national average.

Holmes Beach - "The crime rate in Holmes Beach is 50% lower than the national average.."

Bradenton Beach - "The crime rate in Bradenton Beach is 15% lower than the national average.."

What's the Best Way to Travel 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. Below are some statistics in relation to driving distance that Anna Maria Island, Florida is from some major airports in the area. 

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 it 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.

Popular Best Restaurants on Anna Maria Island, Florida

Anna Maria Island is full of fantastic restaurants. It is a quieter island and does offer a few bars like The Doctor's Office but doesn't offer a large selection of drinking establishments. It is full of a great selection of award-winning bistros and local seafood and farm to table options. Some favorite restaurants include:

  • Rod n Reel Pier for a casual sea-side option for breakfast, lunch, and dinners. 
  • The Sandbar Restaurant, The Beachhouse Restaurant, and Beach Bistro are all great beachfront locations and wonderful to view the sunsets
  • The Bridge Tender Inn, Ocean Star Restaurant in Anna Maria, The City Pier Restaurant, Rod n Reel Pier, Anna Maria Oyster Bar are all great Bayside waterfront restaurants serving up delicious freshly caught seafood.
  • Eat Here Restaurant, The Waterfront Restaurant, Poppo's Taqueria, Skinny's Burgers, and Vinny & Cheryl's Italian Kitchen are also fantastic high and simple cuisine restaurants.

Read more