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.


Properties Available 267 properties available
Blue Crush by Anna Maria Island Accommodations 111 Cedar Ave Anna Maria, Florida VR21-000015Welcome to Blue Crush, a fantastic vacation home with a sparkling pool near Pine Avenue’s shops and restaurants and a quick walk to the sugar-white sands of the Gulf of Mexico. This four-bedroom and three-bathroom getaway is perfect for hosting family and
Hot HOT 58
Blue Crush
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (30)
Highlights • Less than a 10-minute walk from the beach• Pet friendly• Private pool and hot tub• Two blocks from restaurants and shops on Pine Ave• Half a mile from AMI City Pier Mangoes on Magnolia by Anna Maria Island Accommodations313 Magnolia Ave Anna Maria, Florida Your island getaway awaits at Mangoes on Magnolia! This three-bedroom two bath v
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Mangoes on Magnolia
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (12)
Bay Breezes at Bayside Bungalow by AMI Locals 201 S Bay Blvd Bradenton Beach, FL 34217 VR18-000088 Welcome to Bay Breezes at Bayside Bungalow! This adorable Anna Maria Island vacation rental has two bedrooms and one bathroom, all decorated with a delightful coastal theme to give you that perfect beach getaway. With stunning Bay beaches directly ac
Hot HOT 25
Bay Breezes at Bayside Bungalow
Anna Maria Pet Friendly
Bedrooms 2 BR
Bathrooms 1 BA
Guests 6 guests
Rating 5 (63)
Salty Margarita by AMI Locals106 81st St, Holmes Beach, FL 34217Highlights:•1-minute walk to the beach•Heated Pool and Spa•Rooftop deck•Elevator •Ping Pong and Pool Table•Putting Green•Outdoor Dining AreaWelcome to Salty Margarita, a luxury vacation rental just one house from the beach on Anna Maria Island. With sweeping Gulf views from multiple de
Hot HOT 22
Salty Margarita
Holmes Beach
Bedrooms 4 BR
Bathrooms 5 BA
Guests 8 guests
Coconuts Beachfront #107 by AMI Locals Holmes Beach Gulf Front Condo VRC18-000060Experience beachfront bliss at Coconuts Beachfront #107, a beautifully recently refreshed one-bedroom, one-bath condo in Holmes Beach! Just steps from soft sands and sparkling surf, this beachfront vacation rental offers panoramic ocean views, and a private screened-in
Hot HOT 30
Coconuts Beachfront #107
Holmes Beach
Bedrooms 1 BR
Bathrooms 1 BA
Guests 4 guests
Rating 5 (23)
Highlights• Brand New Home with Rooftop Deck• 2-minute walk to the beach• Private Pool and Hot Tub• Near Herb Dolan Park with playground and basketball courtInto the Sunset by Anna Maria Island Accommodations 2516 Avenue CBradenton Beach, FloridaPack your bags for an unbeatable luxury vacation at Into the Sunset! This brand-new home has seven bedro
Hot HOT 41
Into the Sunset
Bradenton Beach
Bedrooms 7 BR
Bathrooms 7 BA
Bathrooms 1 Half Bath
Guests 15 guests
Rating 5 (8)
Highlights • 5-minute walk to the beach • Newly renovated • Private dock • Private pool • Outdoor shower North End Zen by Anna Maria Island Accommodations 112 Hammock Rd Anna Maria, FL 34216 VR16-000360 We warmly welcome you to North End Zen, a four bedroom and three bathroom escape! This stunning canal-front home is a haven for travelers in search
Hot HOT 46
North End Zen
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (28)
Highlights • Canal front home • Private pool • Washer and dryer • Dog friendly with host approval and $250 pet feeLove Shack by Anna Maria Island Accommodations 317 Tarpon St Anna Maria, FL 34216VR16-000399Welcome to Love Shack, an inviting canal-front home with a private pool less than a five-minute drive to Palmetto Ave Beach. This rental has th
Hot HOT 33
Love Shack
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 3 BA
Guests 6 guests
Rating 5 (3)
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
Gone Gulfin'
Anna Maria
Bedrooms 5 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (11)
Highlights• Less than a 10-minute walk from the beach• Private pool and hot tub• Near parks• Outdoor shower• Near restaurants and shopsIsland Mojo by Anna Maria Island Accommodations312 58th StHolmes Beach, FL 34217VRC16-000143Welcome to Island Mojo, an adorable Anna Maria Island getaway with a sparkling pool and hot tub just four blocks from the s
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Island Mojo
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (22)
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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Villa #6 Starfish
Holmes Beach Pet Friendly
Bedrooms 1 BR
Bathrooms 1 BA
Guests 4 guests
Rating 5 (62)
Welcome to The Hideaway!A classic, “Old Florida” style home nestled in the heart of Anna Maria Island! This simple modern, 3 bedroom, 2 bath vacation rental is located less than a block from the sugary sands of the turquoise Gulf waters. Walking distance to cafes, golf cart rentals, island boutiques, and even the local island trolley stop! A beachy
Hot HOT 24
The Hideaway (AMIL)
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (31)

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