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!
15 properties available
Bayfront Paradise by AMI Locals 238 S Harbor Dr, Holmes Beach, FL VRC18-000090 Welcome to Bayfront Paradise by AMI Locals, a spectacular 5-bedroom, 4.5-bathroom canal-front luxury home offering panoramic views of the Bay. Located in a quiet residential area of Holmes Beach, this coastal retreat combines elegance, relaxation, and adventure. With a p
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
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
A Wave From It All by Anna Maria Island Accommodations 404 Spring Ave, Anna Maria, FL, 34216 VR19-000058 / DWE5105449 Welcome to A Wave From It All, a luxurious five-bedroom, six-and-a-half-bath vacation rental in the heart of Anna Maria Island. Just a short seven-minute walk to the island’s white-sand beaches and steps from the boutiques and eate
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
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
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
Dolphin Daze by Anna Maria Island Accommodations 525 75th Street, Holmes Beach, FL 34217 VRC20-000001 Welcome to Dolphin Daze, a spacious five bedroom, four bath canal front vacation home in Holmes Beach, perfectly designed for unforgettable island getaways with family and friends. This Florida Gulf Coast rental features a private heated pool, sce
Honu Hale by Anna Maria Island Accommodations 306 55th St, Holmes Beach, FL 34217 Welcome to Honu Hale by Anna Maria Island Accommodations, a newly renovated three-bedroom, two-bath coastal retreat where tropical charm meets modern comfort. Named after the Hawaiian word for “turtle,” Honu Hale captures the calm, carefree rhythm of island life. Perf
The Curated Palm by Anna Maria Island Accommodations 520 Kumquat Drive, Anna Maria, FL 34216 Welcome to The Curated Palm, a four bedroom, four and a half bath luxury canal-front home designed for multi-family vacations, group getaways, and extended stays. This stunning retreat offers resort-style outdoor living with a private saltwater pool, oversi
Boundless Waves by Exclusive Vacations 408 Magnolia Ave, Anna Maria, FL VR24-000005 Welcome 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 panorami
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