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.

190 properties available

Three Little Birds Cottage by Anna Maria Island Accommodations Welcome to Three Little Birds Cottage by Anna Maria Island Accommodations, a stylish two bedroom, two and a half bath modern retreat with a bonus loft, located just a five-minute walk from the pristine sands of Holmes Beach. Perfect for families or groups, this inviting home offers a pr

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Three Little Birds Cottage

Salt Life by AMI Locals Vacation Rental License #TPL 18-000551, DWE5105473Welcome to Salt Life by AMI Locals, a breathtaking five bedroom, five a half bath bayfront retreat located on the serene south end of Bradenton Beach. Perfect for families, boaters, and beach lovers, this luxury home offers the ultimate Anna Maria Island vacation rental exper

Another Paradise by Anna Maria Island Accommodations Home in Anna Maria, FloridaVR16-000382 Welcome to Another Paradise, a beautifully designed three-bedroom, three-bath coastal retreat located just a two-minute walk from the white sands of Anna Maria Beach. Perfect for families or small groups, this Anna Maria Island accommodation offers a private

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Absolutely Anna by Anna Maria Island Accommodations Home in Anna Maria, FloridaVR16-000095 Welcome to Absolutely Anna, a charming two-bedroom, two-bathroom vacation home with a private pool, cabana lounge, and screened-in porch, just a two-minute walk to Bean Point Beach. This dog-friendly Anna Maria Island rental is the perfect mix of coastal comf

Silver King by Anna Maria Island Accommodations VR16-000118 Welcome to Silver King, a stunning four-bedroom, three-bathroom canal-front vacation home with a bonus bunk room, rooftop deck, and a backyard designed for endless fun. Located just four blocks from the Gulf beaches and three blocks from the charming shops and dining on Pine Avenue, this l

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Take Me Away by AMI Locals VRC20-000170 Welcome to Take Me Away by AMI Locals, a freshly renovated 4-bedroom, 4-bath luxury beach home just a 3-minute walk from the soft sands of Holmes Beach. Designed for families and friends seeking both comfort and style, this coastal retreat offers a private pool, a covered patio with seating and grill, and bri

Bikini So Tiny by AMI Locals Welcome to Bikini So Tiny, a charming one bedroom, one bath pet-friendly vacation rental that captures the character of historic Anna Maria Island with modern comforts. Located right on lively Pine Avenue, you’ll be just a five-minute walk to the beach and steps from boutique shops, local eateries, and island attraction

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

Private Palms by Anna Maria Island Accommodations VRC23-000027Welcome to Private Palms, a beautifully remodeled four-bedroom, two-bath coastal retreat just a 3-minute walk to Holmes Beach and close to the shops and dining of Holmes Beach Towne Center. This bright and stylish home features a private pool, relaxed outdoor living, and comfortable inte

Sweet and Salty by Anna Maria Island Accommodations VRC20-000160Welcome to Sweet and Salty, a luxury vacation home in Holmes Beach featuring four bedrooms and four and a half bathrooms! This modern coastal retreat is perfect for families or groups looking for ultimate relaxation. Enjoy a dazzling private pool and spa, a spacious outdoor patio with

Anna Maria Guest House 212 by Anna Maria Accommodations Cottage in Anna Maria, Florida Experience the relaxed charm of Anna Maria Island at Anna Maria Guest House 212. Located just one and a half blocks from the warm Gulf waters and beaches, this cozy and inviting three-bedroom, two-bath vacation home offers the perfect island escape. Situated abov

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Anna Maria Guest House 212

High Tide Haven by Anna Maria Island Accommodations Welcome to High Tide Haven, a newly renovated three-bedroom, two-bathroom vacation home in the heart of Anna Maria City. Just two blocks from the Gulf beaches and steps from the boutiques and restaurants of Pine Avenue, this elevated villa offers a private heated pool, multiple balconies, and brig

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