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 195 properties available
Bayside Cutie at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #2, Anna Maria, FlVR18-000088Welcome to Bayside Cutie, a charming bayside retreat on Anna Maria Island! This one-bedroom, one-bath condo offers a cozy and stylish escape just across the street from the breathtaking Bay beaches. Enjoy your own private patio where you can sip coffee
Hot HOT 10
Bayside Cutie at Bayside Bungalow
Anna Maria Pet Friendly
Bedrooms 1 BR
Bathrooms 1 BA
Guests 4 guests
Rating 5 (66)
Ocean's 77 by Anna Maria Island Accommodations 205 77th Street, Unit B, Holmes Beach, FL 34217VRC19-000012Welcome to Ocean's 77, a charming beach cottage just five houses from the stunning white sandy beaches of Anna Maria Island’s Holmes Beach! This two-bedroom, two-bath home offers a tropical backyard oasis with a private sparkling pool, a game r
Hot HOT 28
Ocean's 77
Holmes Beach Pet Friendly
Bedrooms 2 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (18)
North End Zen by Anna Maria Island Accommodations 112 Hammock Rd, Anna Maria, FL 34216 VR16-000360 Welcome to North End Zen, a newly renovated four-bedroom, three-bath canal front retreat just a five-minute walk to Anna Maria Beach and steps from Pine Avenue’s boutique shops, cafes, and waterfront dining. Perfect for families and groups, this Anna
Hot HOT 20
North End Zen
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (28)
Anna Maria Guest House 317 by Anna Maria Island Accommodations 317 Pine Avenue, Anna Maria, FL 34216 Welcome to Anna Maria Guest House 317, a charming three-bedroom, two-bath beach cottage located right on Pine Avenue, just two and a half short blocks from the soft white sands of the Gulf beaches. With multiple balconies, cozy living spaces, and a
Anna Maria Guest House 317
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (45)
Costa Bella by Anna Maria Island Accommodations 10107 Gulf Dr, Anna Maria, FL 34216 Welcome to Costa Bella, a four bedroom, four and a half bath luxury vacation home just steps from the beach and Pine Avenue. With chic coastal design, a private pool and spa, and ensuite bathrooms in every bedroom, this home is the perfect choice for families and gr
Hot HOT 25
Costa Bella
Anna Maria Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (15)
Coral Palms by Anna Maria Island Accommodations 209 81st St, Holmes Beach, FL 34217VRC16-000157Welcome to Coral Palms, a beautiful ground level cottage split floorplan vacation home featuring three bedrooms and two bathrooms, perfect for families or groups seeking a relaxing escape on Anna Maria Island. Just a four-minute walk to the sparkling Gulf
Hot HOT 22
Coral Palms
Holmes Beach Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (17)
Gypsy Sol by Anna Maria Island Accommodations 516 Loquat Dr, Anna Maria, FL, 34216 VR18-000034 Welcome to Gypsy Sol, your ultimate Anna Maria Island escape! This four bedroom, two bath canal front vacation home is packed with fun and relaxation, featuring a private pool, hot tub, and ping pong table for endless entertainment. Just a short stroll f
Gypsy Sol
Anna Maria
Bedrooms 4 BR
Bathrooms 2 BA
Guests 8 guests
Rating 5 (27)
It’s a Jungle Out There by Anna Maria Island Accommodations 4002 5th Ave, Holmes Beach, FL 34217 VRC19-000173 Welcome to It’s a Jungle Out There by Anna Maria Island Accommodations, a breathtaking six bedroom, three and a half bath luxury retreat located in the heart of Holmes Beach, just a short stroll from the white sand shores of the Gulf. This
Hot HOT 13
It's a Jungle Out There
Holmes Beach
Bedrooms 6 BR
Bathrooms 3 BA
Bathrooms 1 Half Bath
Guests 12 guests
Rating 5 (31)
Retreat Royale by Anna Maria Accommodations 604 Ambassador Ln, Holmes Beach, FL 34217 VRC19-000265 Welcome to Retreat Royale, a beautifully styled 2-bedroom, 2-bathroom island home nestled in a quiet neighborhood of Holmes Beach on Anna Maria Island! Designed for serenity and long-term stays, this charming retreat features a lush garden oasis, a sp
Retreat Royale
Holmes Beach
Bedrooms 2 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (1)
Beach Cottage by Anna Maria Island Accommodations 211 71st St, Holmes Beach, FL 34217 VRC16-000178 Welcome to Beach Cottage, a charming ground-level vacation home in Holmes Beach, just a 3-minute walk to the white sands of the Gulf beaches. With four bedrooms, three bathrooms, and a private pool and spa, this coastal retreat is ideal for families a
Hot HOT 19
Beach Cottage
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (40)
Bay View Beauty by Exclusive Vacations 881 N Shore Dr, Anna Maria, FL 34216 VR18-000097 Welcome to Bay View Beauty, part of our Exclusive Collection. This luxurious seven-bedroom, seven and a half bath waterfront home with unobstructed bay views. Ideally located along Anna Maria’s North Shore Drive, this luxury retreat places you steps from the whi
EXCLUSIVE COLLECTION EXCLUSIVE COLLECTION
EXCLUSIVE COLLECTION
Bay View Beauty
Anna Maria Pet Friendly
Bedrooms 7 BR
Bathrooms 7 BA
Bathrooms 1 Half Bath
Guests 16 guests
Rating 5 (64)
Casa Allegria by Anna Maria Island Accommodations 209 Archer Way, Anna Maria, FL 34216 VR16-000015 Welcome to Casa Allegria, a charming three-bedroom, two-bath vacation home located just a five-minute walk from Anna Maria Island’s stunning Gulf beaches. This stylish retreat offers modern comfort, a private sparkling pool, and easy access to local
Hot HOT 118
Casa Allegria
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Guests 8 guests
Rating 4.9 (25)

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