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
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
Welcome to Just Beachy on beautiful Anna Maria Island!Have the trip of a lifetime at this beautifully appointed 6 bedroom 4.5 bathroom luxury beach house, just steps away from the sugary soft sandy beaches.This navy and white stunner is settled in the middle of Anna Maria Island, and is 400 feet away from the 65th Street beach access! The home was
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
Highlights • Canal front with private dock and is Pet Friendly• Less than a 10-minute walk to the Manatee County Beach • Private Pool and Hot Tub• Game room with Pool Table and Ping Pong Table Bayfront Paradise by AMI Locals 238 S Harbor Dr Holmes BeachVRC18-000090Welcome to Bayfront Paradise, a truly spectacular vacation home with some of the mos
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
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
Beach Breeze by AMI Locals 205 Elm Ave, Anna Maria, FL 34216 VR16-000510 Welcome to Beach Breeze by AMI Locals, a vibrant four bedroom, three bath coastal retreat perfectly situated in the heart of Anna Maria Island. Just a two-minute walk to the beach and two minutes from Pine Avenue’s charming shops and restaurants, this home combines island styl
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
AMI Breeze by AMI Locals 507 Spring Ave, Anna Maria, FL VR20-000022 Welcome to AMI Breeze! Tucked away in a relaxed neighborhood just minutes from the soft white sands of Anna Maria Beach, this two bedroom, two bath retreat is perfect for families, couples, or friends. With a private heated pool and spa surrounded by lush landscaping, plus styli
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
Salt Life by AMI Locals 112 11th St S, Bradenton Beach, Florida TPL 18-000551 Welcome 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 e
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
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