Anna Maria Island Rentals
196 properties available
Bleuphoria by AMI Locals 112 Elm Avenue, Anna Maria, Florida Welcome to Bleuphoria, a four-bedroom, four-bath luxury beach home on the peaceful North End of Anna Maria Island. Just three houses away from the sugar white sands of the Gulf and steps from Pine Avenue’s boutique shops and restaurants, this designer retreat delivers modern coastal elega
Bleuphoria
House
4
bedrooms
4
baths
8
guests
Island Mojo by Anna Maria Island Accommodations 312 58th St, Holmes Beach, FL 34217 VRC16-000143 Welcome to Island Mojo, a charming three bedroom, two bathroom ground-level home just eleven minutes from the Gulf. Perfectly located near parks, restaurants, shops, and the island trolley, this cozy coastal retreat features a private heated pool, relax
Island Mojo
House
3
bedrooms
2
baths
6
guests
5
(18)
Sunset Terrace 209 by Anna Maria Island Accommodations 2312 Gulf Drive, Unit #209, Bradenton Beach, FL 34217 TPL18-000456 Welcome to Sunset Terrace 209, a two-bedroom, two-bath beachfront condo in Bradenton Beach that’s perfect for couples or small families. This inviting Anna Maria Island accommodation features direct access to the sandy shorelin
Sunset Terrace 209
Condo
2
bedrooms
2
baths
4
guests
5
(12)
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
https://www.exclusivevacations.com/rentals/bay-view-beauty/https://www.exclusivevacations.com/rentals/bay-view-beauty/
Bay View Beauty
House
7
bedrooms
7
baths
1
Half baths
16
guests
Anna Maria Wave by Anna Maria Island Accommodations 2806 Avenue E, Holmes Beach, FL 34217 Welcome to Anna Maria Wave by Anna Maria Island Accommodations, a spectacular four-bedroom, four-bathroom beachfront home that captures the essence of coastal luxury on beautiful Anna Maria Island. Perfect for families and groups, this contemporary retreat com
Anna Maria Wave
House
4
bedrooms
4
baths
8
guests
Bay Breezes at Bayside Bungalow by AMI Locals 201 S Bay Blvd, Unit #1, Anna Maria, FL 34216VR18-000088Welcome to Bay Breezes at Bayside Bungalow, a charming Anna Maria Island vacation rental offering two bedrooms, one bathroom, and a resort-style experience just steps from the beautiful bay and minutes to Anna Maria beaches! This delightful coastal
Bay Breezes at Bayside Bungalow
Villa
2
bedrooms
1
baths
6
guests
Palm Gables 110 by Anna Maria Vacations 110 36th St, Holmes Beach, FL 34217 VRC16-000126 Welcome to Palm Gables 110, a rare Gulf-front three-bedroom, two-bathroom condo perfectly situated in the heart of Holmes Beach on beautiful Anna Maria Island! With bold tropical decor, stunning panoramic views of the ocean, and a private balcony that puts you
Palm Gables 110
Townhouse
3
bedrooms
2
baths
6
guests
5
(23)
Serendipity by Anna Maria Island Accommodations 207 55th St, Holmes Beach, FL 34217VRC16-000107Welcome to Serendipity, a gorgeous villa just a four-minute walk from the pristine white sands of Holmes Beach! This home is all new, with a fully updated kitchen and new furnishings. This elegant single-level duplex features three bedrooms and two bathro
Serendipity
Cottage
3
bedrooms
2
baths
6
guests
5
(8)
Hammock Dreams by Anna Maria Island Accommodations 131 Hammock Rd, Anna Maria, FL 34216 VR16-000408 Welcome to Hammock Dreams! Escape to the peaceful island lifestyle at Hammock Dreams, a stunning canal-front home nestled in the heart of Anna Maria. With three bedrooms, two bathrooms, and a private pool, this tropical retreat is ideal for families
Hammock Dreams
House
3
bedrooms
2
baths
6
guests
5
(7)
Big Nauti by Exclusive Vacations 203 Bay Dr N, Bradenton Beach, Florida TPL22-000071 Welcome to Big Nauti, an extraordinary eight bedroom, eight and a half bath luxury waterfront home that redefines Anna Maria Island living. Located directly on the Bay in Bradenton Beach, this stunning retreat pairs breathtaking panoramic views with resort amenitie
EXCLUSIVE COLLECTION
EXCLUSIVE COLLECTION
https://www.exclusivevacations.com/rentals/big-nauti/https://www.exclusivevacations.com/rentals/big-nauti/
Big Nauti
House
8
bedrooms
8
baths
1
Half baths
18
guests
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
Barefoot by the Bay at Bayside Bungalow
Villa
1
bedrooms
2
baths
6
guests
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
AMI Breeze
House
2
bedrooms
2
baths
6
guests
Tell us what you're looking for and someone will contact you with available options.
Copyright © 2026 • Anna Maria Paradise
All Rights Reserved.