Monthly Vacation Rentals
A month-long getaway is essential for many travelers looking to escape the cold or take their annual vacation in luxury and style. We've put together a list of the perfect Anna Maria Island monthly rentals that feel like your beach home away from home! Filter the features of your desired home and check out nearby activities that will keep you busy. Our monthly vacation rentals are also within walking distance of bars and restaurants for easy dinner solutions. See what Anna Maria Island has to offer during your month-long stay!
24 properties available
Bikini So Tiny by AMI Locals 309 Pine Ave, Anna Maria, Florida 34216 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 shop
Blue Bay by Anna Maria Island Accommodations 205 S Bay Blvd, Anna Maria, FLVPR16-000138Experience the ultimate coastal retreat at Blue Bay, a luxurious and expansive vacation estate offering eight bedrooms and six bathrooms! Located just across the street from the pristine Tampa Bay, this home embodies beachside elegance with breathtaking water vie
Ob La Di Ob La Da by Anna Maria Island Accommodations 442 62nd St, Holmes Beach, FL 34217 Welcome to Ob La Di Ob La Da by Anna Maria Island Accommodations, a cheerful two-bedroom, two-bathroom ground-level retreat in the heart of Holmes Beach! This cozy bungalow radiates charm and good vibes, just like the iconic Beatles tune “life goes on.” Whethe
Coastal Couture by AMI Locals 103 Park Ave, Anna Maria, FL 34216 VR21-000085 Welcome to Coastal Couture, a coastal chic 5 bedroom, 4.5 bath luxury beach home on the north end of Anna Maria Island. You are about a 1-minute walk to Anna Maria Beach and close to Pine Avenue for boutiques, cafes, bike paths, and golf cart rentals. Designed for stylish
Honu Hale by Anna Maria Island Accommodations306 55th St, Holmes Beach, FL 34217Welcome to Honu Hale, your tropical island escape on beautiful Anna Maria Island! “Honu” means “turtle” in Hawaiian—and just like the sea turtle, you’ll find peace, comfort, and the laid-back rhythm of island life in this thoughtfully remodeled coastal retreat.Highlight
Gulf View Beach House by AMI Locals 105 4th St N, Bradenton Beach, FLTPL18-000442Experience tranquility at Gulf View Beach House, a stunning retreat just minutes from Bradenton Beach’s white sands and turquoise waters! This luxurious five-bedroom, three-bath home features panoramic Gulf views from the living room, balconies, and rooftop deck. With
Bay View Bliss by AMI Accommodations 117 7th St N Unit 29, Bradenton Beach, FL 34217 Welcome to Bay View Bliss, a newly remodeled two-bedroom, one bath coastal condo tucked in the heart of Bradenton Beach. Just a block from the beach, steps from the bay, and less than a mile from the vibrant Bridge Street district, this ground floor unit is your pe
Dolphin Daze by Anna Maria Island Accommodations Holmes Beach Canalfront Home with Pool VRC20-000147Welcome to Dolphin Daze, a stunning canal front vacation home with a dock and private heated pool, just a thirteen-minute walk from Holmes Beach! This spacious three-bedroom, four-bath getaway sleeps up to six guests. Perfect for families and friends
Boundless Waves by Anna Maria Island Accommodations408 Magnolia Ave Anna Maria, FloridaWelcome to Boundless Waves, part of our Exclusive Collection. Offering a curated luxury experience with elevated amenities, personalized services, and refined island living. This six-bedroom, six-and-a-half-bath coastal retreat features a rooftop deck with panora
Highlights • Less than a 5-minute walk to the beach • Pool with waterslide and in-ground spa • Rooftop deck • Game room • Elevator Atlantis Beach House by Anna Maria Island Accommodations 2119 Avenue B Bradenton Beach, Florida Escape to paradise at the Atlantis Beach House! This incredible nine-bedroom, six-and-a-half-bathroom home is just a short
On the Flip Side by AMI Locals2210 Avenue A Bradenton Beach, FloridaTPL23-000007Welcome to On the Flip Side, a marvelous getaway with a rooftop deck that boasts water views and an outstanding backyard with a sparkling pool with custom built-ins and an in-ground spa. This home is tucked away in a beachy neighborhood near Tampa Bay and just a quick w
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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