Anna Maria City Vacation Rentals

Located on the North side of Anna Maria Island, Anna Maria City is the perfect destination for those seeking beautiful beaches and a family-friendly atmosphere. This charming "Old Florida" town offers beautiful sunsets and is surrounded on all sides by a beautiful white sand coastline and the tranquil turquoise waters of the Gulf of Mexico. Bean Point Beach and City Pier Park are two of the main beach attractions in this lovely and quaint city. With dolphins, manatees, and other marine life all around, Anna Maria City is a nature and beach lovers paradise. Local food and attractions offer something for everyone in your family, with plenty of activities to keep everyone entertained. Please browse our selection of finely appointed Anna Maria Island vacation rentals offering modern amenities and decorations. Anna Maria Island Accommodations offers the perfect vacation home rentals for your next getaway to Anna Maria City.

Frequently Asked Questions

What is Anna Maria Island known for?
Pristine beaches, crystal-clear waters, a laid-back atmosphere, historic landmarks, fresh seafood, and water activities like fishing, kayaking, and paddleboarding.

How far is Anna Maria Island from Miami?
Approximately 200 miles northwest, about a 3.5 to 4-hour drive.

How far is Anna Maria Island from Clearwater?
Approximately 40 miles south of Clearwater, about 1 to 1.5 hours by car.

264 properties available

Seagrass Sunsets by Anna Maria Island Accommodations101 25th St N Unit 4 Bradenton Beach, FL 34217Welcome to Seagrass Sunsets, a charming 2-bedroom, 2-bathroom coastal condo located just steps from the white-sand shores of Bradenton Beach. Nestled in a modest, low-key building along a quiet street, this relaxing retreat offers a peaceful place to u

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Sunset and Sands by Anna Maria Island Accommodations 200 81st Street Holmes Beach, FL 34217 VRC17-000117 Welcome to Sunset and Sands, your ultimate fun-filled retreat! Gather your crew for unforgettable memories in this four-bedroom, three-bath paradise. You’ll love the private backyard boasting a sparkling pool, in-ground spa, and backyard essent

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Mangoes on Magnolia by Anna Maria Island Accommodations 313 Magnolia Ave, Anna Maria, FL Welcome to Mangoes on Magnolia, your ultimate island retreat nestled just two blocks from the charm and energy of Pine Avenue. This beautifully appointed three-bedroom, two-bathroom vacation home offers the perfect blend of privacy and convenience. With a priva

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Highlights•1 Minute Walk to Beach with Convenient Beach Access•Resort Style Pool and Spa with Tanning Deck•Rooftop Deck with Panoramic Gulf Views•Exciting Backyard Putting Green and Pool Table•Dog friendly with approval and additional fee•Indoor Elevator for Guest convenience•Central location with proximity to Dining and ShoppingExclusive Amenities

EXCLUSIVE COLLECTION

Island Breeze by Anna Maria Island Accommodations235 64th St. Holmes Beach, FL 34217Welcome to Island Breeze! This 3-bedroom, 2-bathroom townhome offers everything you need for a comfortable and convenient vacation, just a 2-minute stroll from the beautiful beaches. Located in a private community, Island Breeze has everything for those who value sp

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Highlights• Brand New Construction• Rooftop Deck • Less than a 5-minute walk to the beach• Private Pool and In-ground Spa• Putting Green and Ping Pong TableGone Gulfin’ by AMI Locals9605 Gulf DriveAnna Maria, FL 34216Get ready for the ultimate beach vacation at Gone Gulfin'! This brand-new, five-bedroom, four-and-a-half-bathroom home is located jus

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Highlights • Private Pool • Less than a 5-minute walk to the beach • Pet friendly + Fenced-In Backyard• Near trolley stop and restaurants • BBQ grill Walking on Sunshine by AMI Locals2906 Gulf Dr Holmes Beach, FloridaVRC19-000232Your dream vacation awaits at Walking on Sunshine, a cute three-bedroom, three-bath getaway a block from the warm sandy b

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Highlights • 2-minute walk from the beach • Private Pool • Elevator • Ping pong table Beach Retreat 208 72nd Street, Unit A Holmes Beach, FL 34217 VRC16-000857 Welcome to Beach Retreat, an amazing vacation home with a private pool that is just a two-minute walk from the white sugary sands of beautiful Holmes Beach! This four-bedroom, three-bathroo

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Highlights•Steps from the Beach with Convenient Beach Access•Resort Style Pool and Spa•Rooftop Deck with Panoramic Gulf Views•Exciting Backyard Putting Green•Dog friendly with approval and additional fee•Fully Equipped Outdoor Kitchen•Close Proximity to Historic Bridge Street Shopping and DiningExclusive Amenities: •6 Seat Club Car Cru Golf Cart fo

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West Coast Best Coast

Highlights• 2-minute walk to the beach• Dog Friendly • Shared Pool• Close to restaurants and grocery stores• BBQ grillVilla #6 Starfish by AMI Locals3605 Gulf Dr, Unit #6 Holmes Beach, FloridaDive into resort-style living at Villa #6 Starfish, a beautiful one-bedroom and one-bath vacation getaway. Island West Resort is a beautiful resort with uniqu

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Pineapple Palms by Anna Maria Island Accommodations Holmes Beach Vacation Home VRC17-000041Welcome to Pineapple Palms, the ultimate ocean-loving getaway just 2.5 blocks from the stunning beaches of Holmes Beach! Perfect for a small family or friends, this charming 2-bedroom, 2-bathroom home offers a private heated pool, lush, landscaped backyard, a

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Coconuts Gulf View #117 by AMI Locals 100 73rd St, Unit #117 Holmes Beach, Florida VRC21-000176 Get ready for an epic friends' getaway at Coconuts Gulf View #117! This two-bedroom, two-bath condo in the beachfront Coconuts complex is all about beach vibes and Florida charm. Plus, it's right next to the Anna Maria Island trolley, making it super eas

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Coconuts Gulf View #117

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