Vacation Rentals

Cancel 14+ days before arrival for a 100% refund or 7-13 days before for a 50% refund.

42 properties available

We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!Cancel 14 days prior to arrival receive 100% refundCancel 7-13 days prior to arrival receive 50% refundExperience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolHurrica

Anna Maria Island Bridge Port Beach Resort

Anna Maria Island Bridge Port Beach Resort 2

Anna Maria Island Bridge Port Beach Resort 3

Anna Maria Island Bridge Port Beach Resort 4

Anna Maria Island Bridge Port Beach Resort

2 BR 2BA Condo

$121^.00 - $527^.00 / per night

Anna Maria Island Beach Palms 6B

2 BR 2BA Condo

$134^.00 - $533^.00 / per night

Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants 3

Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants 4

Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants

2 BR 2BA Condo

$185^.00 - $740^.00 / per night

Island Time-Private Beach Access-Heated Pool-Water Views 3

Island Time-Private Beach Access-Heated Pool-Water Views 4

Island Time-Private Beach Access-Heated Pool-Water Views

2 BR 2BA Condo

$152^.00 - $592^.00 / per night

HOT 22

Anna Maria Island Beach Palms 5B

2 BR 2BA Condo

$177^.00 - $667^.00 / per night

Welcome to Cottage Lighthouse! This beautiful and charming holiday home located in Bradenton Beach is a short walk to the beautiful white sands of the Gulf of Mexico. This quaint cottage offers air-conditioned accommodations with its very own private backyard with patio eating area, propane grill and free WiFi. It features 1 bedroom (Queen bed) wit

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks 2

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks 3

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks 4

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

1BR 1BR Cottage

$3,000^.00 - $7,246^.00 / per night

Anna Maria Island Beach Palace

4BR 3BA House

$413^.00 - $1,485^.00 / per night

The Sunshine Kissed Villa has everything you need for a complete holiday! Our villa has all you need for staying in, and when you are ready to get out you are moments away from anything that sparks your interest. Your dream tropical getaway awaits on Anna Maria Island, Florida! Located on the Gulf of Mexico, less than 1-hour from Tampa or Sarasota

Anna Maria Island Sunshine Kiss Villa

2 BR 2BA Condo

$114^.00 - $431^.00 / per night

HOT 21

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach 3

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach 4

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach

2 BR 2 1/2 BA Condo

$120^.00 - $558^.00 / per night

Boasting a large, resort style heated outdoor pool with a hot tub, and a prime location on Anna Maria it's easy to fall in love with this island getaway. The private location on the north end of Anna Maria Island, near Bean Point is ideal to give you space and privacy and only a five minute walk to all local food and activities.Perfect for a romant

Serenity Cottage

2BR 2 BR Cottage

$2,000^.00 - $4,779^.00 / per night

1 bedrooms

4 guests

Anna Maria Island Retreat

2 BR 2BA Condo

$167^.00 - $629^.00 / per night

Relax on the 3rd floor veranda, and gaze out across the serene aquamarine waters of the Gulf of Mexico. The sea breeze is scented with jasmine and frangipani. Fresh air and sounds of the surf will lower your blood pressure and make you glad to be alive! This elegant, sunshine-yellow, 4br/3ba, Victorian-style vacation home will help you to cherish e