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Anna Maria Vacations Holmes Beach

Book Your Anna Maria Island Beachfront Vacation Rental

Things to do in Holmes Beach! | Anna Maria Island

Anna Maria Vacations has been serving the Anna Maria Island community for a long time. Our team is here to help you plan your dream vacation, offering so many Anna Maria Island Rentals for you to pick from. Once you find the best beachfront rental, go ahead and reserve it right here on our site. If you have any questions feel free to contact us. We also have specially selected luxury vacation rentals and 5+ Bedroom rental properties for more fun!

Holmes Beach Vacation Accommodation Rentals

Located on Anna Maria Island off the Gulf Coast of Florida, Holmes Beach is a small, friendly and charming Old Florida town, with a wonderful all year climate and beautiful sunsets perfect for your vacation escape!

With a population in the region of 5,000 residents a blend of permanent and seasonal, Holmes Beach is the largest of three island communities on Anna Maria Island. Bordered to the north by the City of Anna Maria and to the south by the city of Bradenton Beach, Holmes Beach boasts three miles of gorgeous white, sandy beaches.

At Holmes Beach you will find your perfect vacation rental accommodation. Here at Anna Maria Vacations we specialise in luxury rentals throughout Holmes and Anna Maria Island. Whether you are seeking a small intimate villa for your romantic getaway, a beautiful beach front condo rental, bay front rentals with docks, or a large villa with pool and elevator we have 1-8 bed vacation accommodation to suit, with plentiful beach front rentals.

The city of Holmes Beach itself provides everything you will need for your vacation stay, our small, quaint town offering restaurants, bars and retail outlets with some local history culture, parks and wildlife thrown in!

When you are not too busy relaxing. You will also find fitness, fishing and water sports facilities of course not forgetting our beautiful sugar white sand beaches with lifeguards, excellent washroom and child facilities.

Anna Maria Island The Perfect Beach Destination

What do you picture when you think of the perfect beach getaway? Sandcastle competitions? A fishing pier towering over deep blue waves? White sand dotted with seashells and dolphins silhouetted by the setting sun? Great seafood restaurants with character and outstanding menus? What about beachfront rentals, pet-friendly vacation rentals sheltered by lush gardens, or vacation rentals located close to shopping?

Throw in a free trolley line and you have Anna Maria Island located on the gulf coast of Old Florida. After receiving the 2014 Travelers Choice Award as the #3 Island in America from Trip Advisor, people have started giving this relaxing and fun destination credit for being a quaint oasis, but it still keeps its charm and small-town feel. The seven-mile island is packed with activities, but not packed with people. Sail, fish, swim, bike, kayak, shop, and explore by day, and relax at night in one of our bright and colorful Anna Maria Island vacation rentals!

Many have been recently renovated, and have luxury amenities like heated pools, king-sized beds, Wi-Fi, and fully equipped kitchens. Gather for grilling parties with your whole family or group rentals with 1-5+ bedroom accommodations, and plan on bringing four-legged friends because we offer many Anna Maria Island pet-friendly vacation rentals as well.

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Anna Maria Island Homes With 4 To 8 Bedrooms

Anna Maria Island is home to some of the best beaches in Florida. In addition, AMI boasts fantastic fishing, delicious restaurants, plenty of sweet shops and of course an abundant collection of large vacation rental homes. Almost all of our four to eight bedroom homes on this page are outfitted with a private heated pool and many of these rentals have hot tubs. We have a great inventory of Anna Maria Island homes that can sleep 8 or more people. Feel free to use the Filter tool to help narrow down your search. It will help you locate the perfect home for your needs. From beachfront and canalfront to homes with fun & games, we have something for every group and every budget. Happy searching.

Luxury Vacation Rentals On Anna Maria Island


Some members of our team were born and raised here, others migrated here, but all of us are now Locals. This area is incredibly special, so we want to make sure your experience on Anna Maria Island, Bradenton Beach, and Holmes Beach is better than anyone else could offer.

Our focus is on you, our guest, during your Anna Maria Island vacation rental, customizing vacations to meet your needs, and providing deeper experiences through the use of our local knowledge. Stay with us, and vacation like a local!

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Guest Reviews

Our little family of three enjoyed our relaxing stay in AMI. Short walk to the beach and the pool was lovely.We had a plumbing issue during our stay at the house but we had Immediate access to the manager even though it was quite late at night. Plumbers were on site within an hour and quick action was taken to get the repairs completed by the next day.Love the little town and enjoyed the sandbar at sunset as well as the ice cream shops!Thank you for sharing your home.~ Jennifer M.

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Stay With Island Vacation Properties

When youre searching through Anna Maria Island accommodations, youre probably looking for somewhere safe, comfortable, and affordable with plenty of room for your entire group. At Island Vacation Properties, weve got all that and more! Our team is always happy to help you select your ideal rental and tell you all about the incredible sites of Anna Maria Island, guaranteeing that you have the vacation of your dreams. Theres never been a better time to escape your worries and retreat to the Old Florida paradise of Anna Maria Island!

City Of Anna Maria Vacation Accommodation Rentals

Located in the North of Anna Maria Island off the Gulf Coast of Florida, Anna Maria City is a small, friendly and charming Old Florida town, with a wonderful all year climate and beautiful sunsets perfect for your vacation escape!

With a population in the region of 2,000 residents a blend of permanent and seasonal, Anna Maria City is one of three island communities on Anna Maria Island, neighbored with the small island cities of Bradenton Beach and Holmes Beach.

In Anna Maria City you will find your perfect vacation rental accommodation. Here at Anna Maria Vacations we specialise in luxury rentals throughout Anna Maria City and across the Island. Whether you are seeking a small intimate villa for your romantic getaway, a beautiful beach front condo rental, bay front rentals with docks, or a large villa with pool and elevator we have 1-8 bed vacation accommodation to suit, with plentiful beach front rentals.

The city of Anna Maria itself provides everything you will need for your vacation stay, our small, quaint town offering restaurants, bars and retail outlets with some local history culture, parks and wildlife thrown in!

Because of its position in the North of the island, Anna Maria City is blessed with wonderful views and sunsets over the Gulf, which serves as inspiration for budding artists. Several boutique art galleries can be found in the city. Bottle nose dolphins and manatees are also common sightings!

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Things To Do On Anna Maria Island

Our Anna Maria Island, Florida, beachfront rentals provide all the amenities one would need to make the most out of their vacation. Over the last decade, AMI has put itself on the map as one of the best islands in the world and the best in Florida. Our Anna Maria Island beaches are as stunning as any other vacation destination on the Gulf or the East Coast. Enjoy some of the best island fishing and gorgeous Anna Maria Island sunsets and return to one of our amazing beachfront vacation rental homes.

Vacation Home Inholmes Beach Florida

Holmes Beach eliminates nearly 1,100 beach parking spots on Anna Maria Island
1 Twin over Twin Bunk Bed – 5 King Bed
Bathrooms: 5 Full, 1 Half Bathrooms
Virtual Tour:
  • Daily Rates from $500to $3,745per night
  • Weekly Rates from $2,625to $8,400per week
  • Minimum Stay: 7 Days
  • On our Professional Linen Service Program
  • 6 bedroom and 5.5 bathroom luxury private home
  • Multiple covered decks-Gulf water views
  • Just a short 1 minute walk to the beach
  • 5 Kings and 1 set of bunk beds-sleeps 12 in beds
  • Private heated pool with sun deck and spa, outdoor shower and covered lanai
  • Short 10 minute stroll to local eateries and shops on North AMI
  • Wireless Internet and 8 Flat Screen TV’s
  • Gourmet kitchen with stainless steel appliances, granite throughout


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What Makes Holmes Beach Special

Holmes Beach is a tiny little encapsulation of everything that makes coastal cities lovely. Right between the city-esque appeal of Bradenton and the Old Florida quaintness of Anna Maria , Holmes Beach manages to capture the best of both worlds. Its an exciting community on Anna Maria Island, filled with gorgeous vacation rentals.

The City of Anna Maria is directly north of this area, and guests can indulge in its many attractions with a quick drive or free trolley ride right from their accommodations. Holmes Beach itself also features one of the most frequently visited and scenic beaches on the Gulf of Mexico: Manatee Public Beach. Or venture directly south into the quaint and laid-back setting of Bradenton Beach. No matter how you plan on spending your time on Anna Maria Island, these Holmes Beach vacation rentals are sure to please your entire group.

Great For Couples And Small Families

The house is open and light with plenty of space to relax in. Its over three floors, garage level first floor with cooking cleaning facilities and sitting room with balcony access. Top floor is bedrooms, so if you have trouble with stairs you may need to factor this, but the stairways are wide and easy to use. Bars and restaurants are within walking distance, as is the beach and pool. Great for couples and small families.

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Is Anna Maria Island A Good Place To Rent A Vacation Rental

Anna Maria Island Vacation Rentals

Found on Florida’s Southwest Gulf coast with 7 miles of pristine beaches and 4 miles wide, Anna Maria Island offers an abundance of vacation rentals on the beach, with private pools and in waterfront spots along the island.

Anna Maria Island has thousands of unique and gorgeous vacation rentals to choose from. If you are looking for a beachfront holiday or a rental with a dock to fish and boat from, Anna Maria is one of the best areas in Florida to rent a beach house, condo or pool home.

What Is The Difference Between Anna Maria And Anna Maria Island


For sure this can be confusing. Anna Maria Island is made up of three cities. Bradenton Beach, the most Southern City. Holmes Beach which is in the middle of the Island and the most Northern City is Anna Maria City. So when someone refers to Anna Maria it could be short for Anna Maria Island or it could be short for Anna Maria City. Most of the time when a local references Anna Maria means Anna Maria City.

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Wildlife And Water Sports In Anna Maria Island Beaches

Whether you want to hit the waves, sun on the sand, or view the wildlife, Anna Maria Island has a variety of unique beaches that cater to different vacationers. Vacation home rentals can put you right in the heart of the beautiful beaches, such as Manatee Public Beach, a soft-sand beach with clear turquoise waters, or Coquina Beach, a pristine natural beach with a backdrop of Australian pine trees. You could also try you luck spotting sea turtles nesting at Anna Maria Beach, or experience the quiet Florida lifestyle at Bayfront Park, a beachfront location with a pier and seaside attractions.

What Are Some Fun Things To Do On Anna Maria Island

While staying in an Anna Maria Island rental there are tons of activities available to you. The island is best known for its soft, sandy beaches and stunning turquoise water. With seven miles of beach to explore, there’s plenty to keep the kids and parents entertained. If you want to shake things up on your trip, check out what the locals say are the best things to do on Anna Maria Island.

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Things To Do In Anna Maria

Once youve made yourself at home in one of our Anna Maria vacation rentals, you can get out and start exploring! In the City of Anna Maria, youll find the popular Pine Avenue for all of your shopping needs. Add something new to your closet at the Pink and Navy Boutique or pick up a souvenir at Bella by the Sea Home Boutique. Grab a quick treat at Anna Maria Donuts or sit down for a family meal at Rod and Reel Pier Restaurant. Check out a show at The Island Players or learn about the area at the Anna Maria Island Historical Museum and Park. No matter what you and your group are interested in it, you can find it here!

Beaches Of Anna Maria Island

Take a look at Anna Maria Beach Resort

Whats the difference between Anna Maria Island and the city of Anna Maria? Where is Bradenton Beach in relation to the city of Bradenton? The City of Anna Maria is located at the northern end of Anna Maria Island. Holmes Beach is in the middle section of the island right off Highway 64 , next to the Manatee Public Beach. Bradenton Beach is at the southern tip of Anna Maria Island, off Highway 684 . The City of Bradenton is located about 20 minutes inland from Anna Maria Island, next to the famous Manatee River. Longboat Key is the island just south of Anna Maria Island and is easily accessible via the main road, Highway 789 .

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What Sort Of Restaurants Are On Anna Maria Island

The island has a vast collection of unique eateries to choose from, offering everything from gourmet donuts to delectable sushi to mouthwatering seafood. The island is proud to offer such a wide selection of restaurants that are not chain restaurants and unique to the island. To see more of our restaurant selection check out the dining and nightlife page of our site.

Where Can I Find Your Vacation Rentals On Anna Maria Island

Our vacation rental properties are spread throughout Anna Maria Island, giving our guests the power to choose where they want to stay on the island. For those traveling with their dogs, we offer pet friendly vacation rentals that are perfect for the whole family. To be as close to the ocean as possible, be sure to check out our beachfront rentals.

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About Island Vacation Properties

Island Vacation Properties, LLC was founded in July, 2000 by Ann Caron, a real estate broker with fourteen years of property management experience on Anna Maria Island. It was Anns firm belief that by providing unique services otherwise unavailable to property owners and guests, Island Vacation Properties would fill a void desperately needed in the marketplace. By focusing on ethical behavior and quality service, she knew that a competitive advantage was attainable. She also believed that the opportunity existed to cultivate trust and integrity into the real estate and property management field on Anna Maria Island. When Ann retired in 2016 Bill and Sara Annis bought the company and carry on Anns founding beliefs. Sara has been with Island Vacation Properties since 2005 and at the time of purchase was the rental manager. Bill joined Island Vacation Properties in 2013 as a sales agent and a CAM associate.

Starting with less than forty rentals in mid 2000, we have today numbered 250 properties, making us one of the top rental offices on Anna Maria Island. Property managers include Ken Richards, Susan Hollub, Jason Mooney and Amy Niedzwick.

The company is also actively involved in condominium management under Michael Northfield Community Association Managers leadership and Ellsworth Helms assistance.

Where Is Anna Maria Island Located

Breezy Beach: Anna Maria Island 4 Bedroom Pet Friendly ...

Anna Maria Island is 109 miles west of Florida as the crow flies, but it’s just over 117 miles by car. It’s about an hour and a half southwest of Tampa International Airport and 30 minutes northwest of the Sarasora-Bradenton International Airport. Anna Maria Island is also abour 2 hours southwest of Orlando and Disney World.

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Anna Maria Island Beachfront Vacation Rentals

Anna Maria Island boasts some of the best beachfront vacation rentals in the area. We have stunningly clear turquoise waters and some of the softest sand in the world. The breaking waves are right outside your door. So relax, leave the business behind, get away from the hustle and bustle of city life, and find yourself in one of our beachfront vacation rentals. Return to your Anna Maria Island beachfront rental and experience amenities like:

  • Spacious and inviting homes
  • Breathtaking views of the Gulf
  • Close proximity to AMI attractions
  • High-speed internet access

Family Fun In The Sun In Holmes Beach

For shining sands and stunning seas, Manatee Public Beach is a must! There is so much family fun to be had in the sun here with volleyball nets lying in wait as well as picnic tables, a childrens playground and even a beach-side cafe. Hop on the free Holmes Beach trolley and head downtown for some retail therapy or enjoy some fabulous fresh seafood in one of the towns restaurants. Appreciate the art by spending an afternoon enjoying the towns art galleries. You never know, you may even find a special souvenir!

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