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!


Properties Available 25 properties available
Walking on Sunshine by AMI Locals 2906 Gulf Dr, Holmes Beach, Florida VRC19-000232 Welcome to Walking on Sunshine by AMI Locals, a stylish three-bedroom, three-bath coastal getaway located just one block from the pristine sands of Holmes Beach. Perfect for families and pet owners, this Anna Maria Island vacation rental features a private pool, a fe
Hot HOT 16
Walking on Sunshine
Holmes Beach Pet Friendly
Bedrooms 3 BR
Bathrooms 3 BA
Guests 6 guests
Rating 5 (59)
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
Hot HOT 13
AMI Breeze
Anna Maria Pet Friendly
Bedrooms 2 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (30)
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
Hot HOT 63
Bay View Bliss
Bradenton Beach
Bedrooms 2 BR
Bathrooms 1 BA
Guests 4 guests
Rating 5 (2)
The Hideaway by AMI Locals 117 Palm Ave, Anna Maria, FL 34216VR16-000481Welcome to The Hideaway, an Old Florida style home nestled in the heart of Anna Maria Island! This charming, modern three-bedroom, two-bath vacation rental is less than a block from the soft sands of Anna Maria Beach! Located within walking distance to cafes, boutique shops, go
The Hideaway (AMIL)
Anna Maria Pet Friendly
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 4.9 (40)
Barefoot by the Bay at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #3, Anna Maria, FL 34216VR18-000088Welcome to Barefoot by the Bay, a luxury ground-level villa offering one bedroom, two bathrooms, and a cozy den in a picturesque bayside setting! Located just across the street from beautiful Bay and within walking distance of the beach, re
Hot HOT 29
Barefoot by the Bay at Bayside Bungalow
Anna Maria Pet Friendly
Bedrooms 1 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (73)
Gulf Horizons by AMI Locals 201 17th St N, Bradenton Beach, FL VPL22-000084Experience the ultimate Florida escape at Gulf Horizons, a spectacular three-level estate with seven bedrooms and six and a half bathrooms! Located just across the street from Bradenton Beach's pristine Gulf beaches, this home offers panoramic water views from the rooftop de
Hot HOT 13
Gulf Horizons
Bradenton Beach Pet Friendly
Bedrooms 7 BR
Bathrooms 6 BA
Bathrooms 1 Half Bath
Guests 16 guests
Rating 5 (53)
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
Hot HOT 39
The Curated Palm
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (4)
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
Hot HOT 23
Dolphin Daze
Holmes Beach
Bedrooms 3 BR
Bathrooms 4 BA
Guests 6 guests
Coconut Cove by AMI Locals 205 17th St N, Bradenton Beach, Florida TPL22-000085 Welcome to Coconut Cove by AMI Locals, a vibrant six bedroom, four and a half bath luxury beach home just a three-minute walk from the soft sands of Bradenton Beach. Perfectly designed for families and groups, this retreat combines island style, modern comfort, and endl
Hot HOT 16
Coconut Cove
Bradenton Beach Pet Friendly
Bedrooms 6 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 14 guests
Rating 5 (76)
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
Hot HOT 15
Gulf View Beach House
Bradenton Beach Pet Friendly
Bedrooms 5 BR
Bathrooms 3 BA
Guests 15 guests
Rating 5 (67)
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
Salt Life
Bradenton Beach Pet Friendly
Bedrooms 5 BR
Bathrooms 5 BA
Bathrooms 1 Half Bath
Guests 11 guests
Rating 5 (40)
Atlantis Beach House by Anna Maria Island Accommodations 2119 Avenue B, Bradenton Beach, Florida RBT17-003063 / TPL18-000446 Welcome to Atlantis Beach House by Anna Maria Island Accommodations, an extraordinary nine bedroom, six and a half bath coastal retreat just a two-minute walk from the Gulf. Designed for unforgettable family gatherings and gr
Hot HOT 13
Atlantis Beach House
Bradenton Beach Pet Friendly
Bedrooms 9 BR
Bathrooms 6 BA
Bathrooms 1 Half Bath
Guests 23 guests
Rating 5 (73)

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