Anna Maria City Vacation Rentals
One of the best ways to experience all that the island has to offer is by staying in an Anna Maria vacation rental. These rentals come in all shapes and sizes, from cozy cottages and beachfront Anna Maria rentals to luxurious waterfront homes, and offer all the comforts of home with the added convenience of being steps away from the beach and all the island's top attractions. With so many options to choose from, you're sure to find the perfect rental for your dream vacation.
Anna Maria City is a picturesque, charming town located at the northern tip of Anna Maria Island - located just off Florida's gulf coast near Tampa. This island paradise is a perfect destination for anyone looking for a quiet and peaceful vacation away from the hustle and bustle of the city. You won't find chain stores or chain restaurants in Anna Maria, but you will find crystal-clear waters and soft sandy beaches. Anna Maria City offers a perfect setting for a relaxed vacation. One of the main attractions of Anna Maria City has to be its pristine soft white sand beaches. Fill your days with sunbathing, swimming, or enjoying water sports - Anna Maria City is sure to have something for everyone. The beaches are perfect for strolling or jogging, and you can always take a break to soak up the sun and enjoy the stunning views of the Gulf of Mexico.
Read on to learn more about our Anna Maria vacation rentals as well as all the benefits of staying with Island Real Estate.
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Discover the allure of Anna Maria Island's northern end with the delightful "Mango Beach House." This idyllic beach cottage features 3 bedrooms and 2 bathrooms, comfortably accommodating up to 8 guests with 2 King beds, 1 Queen bed, and 2 Twin beds (bunkbed).<br /><br />Relax on the secluded sugar sand beach of Bean Point, which is just a short str
Mango Beach House
Home- 3
- 2
- No Pets
- Sleeps 8
- 40 Views
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Following a beautifully sculpted path will lead you to a tropical archway of two large coconut trees, there you’ll fine your own piece of island paradise. “Anna Maria Cottage” is an island oasis that's more than worthy of its name sake. This island cottage, placed perfectly near the beaches of Anna Maria, is a treat for the eyes. Inside you’ll find
Anna Maria Cottage
Home- 3
- 3 Full Baths , 1 Half Baths
- Pool
- Dogs Allowed
- Sleeps 6
- 31 Views
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Relax and unwind in the luxurious Anna Maria Island vacation rental home “Beach Pearl”. This five star rental has everything experienced vacationers look for in a home from the perfect location to well-appointed amenities. Just a block and a half from the powder sand beaches of Anna Maria City, “Beach Pearl” is the quintessential Anna Maria Island
Beach Pearl
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 33 Views
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Fall in love with Anna Maria Island paradise when you vacation at “Over the Moonl”! This gorgeous three bedroom, private heated pool getaway accommodates up to six guests with a king bed, a queen bed and two twin beds in this ground level single family home located in the coveted north end of Anna Maria. <br /><br />The city of Anna Maria boasts so
Over the Moon
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 37 Views
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Located on beautiful canal front property in Anna Maria City, 230 Chilson Avenue "Sand Dollar Dream" is the perfect spot for a Florida vacation with a brand new, private, heated pool and spa. Relax in spacious back yard swaying the hammock amongst the lush tropical landscaping, or roast s'mores in the fire pit seating area. This lovely renovated ho
Sand Dollar Dream
Home- 4
- 2
- Pool
- Dogs Allowed
- Sleeps 8
- 30 Views
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On Anna Maria Island nothing is far from the beach, and "Maria's Way" is no exception. Walk just a short distance, about two blocks north, to the island most secluded powder sand beaches at beautiful Bean Point https://www.islandreal.com/bean-point-vacation-rentals. Not only close to the beach, also enjoy nearby Pine Avenue boutiques, restaurants a
Marias Way
Home- 3
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 35 Views
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This elevated villa boasts a private heated pool and a fenced yard. Step into the ultimate home away from home, nestled in the heart of Anna Maria city, directly along historic Pine Ave. During the updates the aim was to both preserve the charming village atmosphere of the street and create a versatile environment for boutique shopping, dining, and
AMI Outpost
Multi-Family- 3
- 2
- Pool
- Dogs Allowed
- Sleeps 8
- 48 Views
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When you visit Anna Maria Island vacation rental “A Mermaid's Tale” you are sure to have an amazing Florida getaway! Sleep up to six guests in luxury and style. This three bedroom rental is just a short stroll to the best beaches you’ll find on the gulf coast. A trip to the beach was never this much fun! When you enter “A Mermaid's Tale” you’ll be
A Mermaids Tale
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 49 Views
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“Summer Breeze” is one of the premier homes on the island. The perfect home for an Anna Maria Island getaway. With tropical landscaping, updated inside and out, and this rental home is stunning on all fronts. Elevated, high-end tropical décor, and pristine floors, “Summer Breeze” is love at first sight. Five large bedrooms, a spacious layout, this
Summer Breeze
Home- 5
- 4
- Pool
- Dogs Allowed
- Sleeps 14
- 34 Views
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The perfect spot for an extended island getaway, 523 Loquat is a stunning three bedroom, 3 full bathrooms, canal front Anna Maria Island vacation rental home with accommodations for up 6 guests in casual island style luxury. <br /><br />523 Loquat is located in a coveted vacation destination in the city of Anna Maria just a short walk to Pine Avenu
Orions Beach House
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 25 Views
Best Neighborhoods for Anna Maria Vacation Rentals
The number one way to find the perfect Anna Maria vacation rental is to find the perfect neighborhood within the City of Anna Maria. The neighborhood that catches the eye of our guests the most will most likely provide the best Anna Maria vacation rental experience for them!
Don't worry, Island Real Estate knows the importance surrounding finding the best neighborhood for Anna Maria vacation rentals. Therefore, we have compiled a list of the best neighborhoods to choose from!
- Bean Point - The neighborhood of Bean Point has the founding history of the island incorporated into stunning views and pristine white beaches, with quiet surroundings. This neighborhood is a tad more secluded than others in the city. The Anna Maria vacation rentals on Bean Point are situated in prime locations, close to the beach, and offer a range of amenities for a comfortable and memorable vacation. Whether our guests are looking for a cozy cottage or a luxurious waterfront home, Bean Point has a wide variety of Anna Maria vacation rentals to choose from, making it perfect for any type of getaway.
- Gulf Drive - Gulf Drive is a stunning neighborhood located on the western side of the City of Anna Maria. Palmetto Ave Beach is just a few steps away no matter where our guests stay in the neighborhood. Our Gulf Drive Anna Maria vacation rentals range from quaint and charming cottages to elegant homes with enough room for the whole family to enjoy. Heated pools, hot tubs, and plenty of indoor and outdoor space are just a few of the perks our guests enjoy when relaxing in their beachfront Anna Maria vacation rental.
- North Shore Drive - North Shore Drive offers marvelous views of the ocean and beachfront, as well as easy access to the historical area of Bean Point. This area offers a more secluded Anna Maria vacation rental experience compared to others located within the town. Our guests are able to walk to the Rod and Reel pier to enjoy a delicious meal and some fishing, as well as rent a bicycle built for two, or a beach cruiser to enjoy the scenery while cruising around like in the 50s.
Outdoor Activities in Anna Maria City
If you're looking for outdoor activities, Anna Maria City has plenty to offer. You can rent a bike and explore the island's many bike trails, or go kayaking and explore the mangrove tunnels. You can also try your hand at fishing, either by hiring a local guide or casting your line off one of the island's many piers.
Why Anna Maria Vacation Rentals Are The Best On Anna Maria Island
The City of Anna Maria is a prime location for vacation rentals on the island, offering a unique blend of old Florida charm and modern amenities. The beaches, streets, and overall atmosphere of the city is clean, welcoming, and relaxing. Compared to Bradenton and Holmes Beach, Anna Maria City has a more laid-back and intimate atmosphere, making it the perfect destination for those looking to escape crowds and experience a true island getaway. Many of the activities, attractions, and sightseeing opportunities are located in the City of Anna Maria which is the most beneficial to Anna Maria vacation rental guests, as they never have to travel far to reach their destination.
Anna Maria vacation rentals within Anna Maria City are luxurious and well-maintained, with many properties featuring private pools, fully equipped kitchens, and beautiful views of the Gulf of Mexico. Furthermore, Anna Maria City is known for having the best beaches on the island, which are only steps away from most vacation rentals. The City of Anna Maria is also a walkable town, with many restaurants, shops, and activities close to the rentals, making it a convenient and enjoyable place to stay. For those that don’t want to walk, there are plenty of easy modes of transportation to choose from without having to spend an arm and a leg.
Getting Around Anna Maria, FL
There are a variety of ways for our guests to travel to and from their Anna Maria vacation rental. One of the biggest reasons why our guests choose to visit Anna Maria is the fact that there is no need for a rental car. Our small island makes it extremely easy and efficient for guests to travel wherever they please in Anna Maria without hassle, or delay. Here are the top recommended modes of transportation for guests at Anna Maria vacation rentals.
- Free Trolley - Anna Maria offers a free air-conditioned, or open-air, a trolley that frequents all the important places on the island. Vacationers love to sit back, relax, and take in the scenery as they are transported wherever they please. The trolley service starts at 6 am and arrives at each stop in 20-minute intervals until 9 pm. After 9 pm the trolley continues to reach each stop every 30 minutes, until 10:30 pm.
- Monkey Bus - The Monkey Bus is free for tips ride service that travels all over Anna Maria. They offer rides as small as to a local restaurant or to the other end of the island. This bus is also not just limited to transporting guests around the island. They also have the ability to cross bridges into other towns as well
- Airport Ride Service/Ride Shares - While Anna Maria is a smaller area compared to other towns and cities in Florida, there are still ride-share options available, such as Uber and Lyft. If guests are looking for transportation from their Anna Maria vacation rental to the airport, there are local driving services available to do so. Our team has all the information necessary to assist our guests with setting up transportation when they arrive.
Why Choose Island Real Estate
Our team at Island Real Estate prides itself on our ability to provide our guests with the best Anna Maria vacation rental experience the island has to offer. Not only do we provide pristine condition Anna Maria vacation rentals with heated pools and full-service kitchens, but we also offer our knowledge and years of experience to inform our guests of all the amazing experiences and adventures they can encounter while staying with us. To book your Anna Maria vacation rental, or to learn more about the many amenities we have to offer, contact our team at Island Real Estate today!
What A Happy Client Says About Island Real Estate Vacations on Google
We have used multiple rental agencies over the years and decided to try Island Real Estate. Never have we had such prompt and courteous service. Had a minor issue with the microwave not working. Briana answered our email within minutes and was at the door in an hour with a new microwave......on a Sunday! Also, our pool was not due for cleaning yet but we had written and asked for it to be earlier and the guy was at our rental within 15 minutes. Great service. Thank you!
Jen M.
5/5 Star Rating