Vacation Rentals

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


Properties Available 43 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 Pool​Hurrica
Hot HOT 29
Anna Maria Island Beach Sands 201
2 BR 2BA Condo
$268.00 - $939.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (46)
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 PoolWhat's I
Hot HOT 77
Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach
2 BR 2 1/2 BA Condo Pet Friendly
$151.00 - $526.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
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 the sounds of the surf will lower your blood pressure and make you glad to be alive! This elegant, sunshine-yellow, 4br/3ba vacation home will help you to cherish every sunrise
Anna Maria Island Sun's Up B
4BR 3BA House
$3,000.00 - $7,243.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (11)
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 Pool​Hurrica
Hot HOT 22
Anna Maria Island Beach Palms 2A
2 BR 2BA Condo
$142.00 - $516.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (28)
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 Pool​Hurrica
Hot HOT 24
Anna Maria Island Bridge Port Beach Resort
2 BR 2BA Condo
$142.00 - $490.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (16)
Relax on the lanai, sip your morning coffee or freshly squeezed citrus juice. The sea breeze is scented with jasmine and frangipani. Fresh air and the sounds of the surf will lower your blood pressure and make you glad to be alive! Anna Maria Island Coquina Tropics is a second-floor, 2br/2ba condo in the seashell-pink Coquina Moorings development,
Hot HOT 27
Coquina Tropics-3 Bedrooms- Bathroom-Water Views From Every Room
3 BR - 2BR Condo
$211.00 - $717.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (12)
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
Hot HOT 20
Anna Maria Island Sunshine Kiss Villa
2 BR 2BA Condo
$114.00 - $431.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 (10)
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 PoolGulf of
Hot HOT 72
Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants
2 BR 2BA Condo
$199.00 - $707.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.8 (7)
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 Pool​Hurrica
Hot HOT 20
Anna Maria Island Beach Palms 6B
2 BR 2BA Condo
$142.00 - $516.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.6 (38)
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% refund​Hurricane Update:The entire complex is built on pillars more than 20 feet o
Anna Maria Island Beach Bay Breeze
2 BR 2BA Condo
$147.00 - $516.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (8)
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
Bedrooms 1 bedrooms
Guests 4 guests
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 PoolEnchanti
Hot HOT 39
AMI Gulf Lookout-Views Of The Gulf From Every Room-Rooftop Terrace
3BR 2BR House
$297.00 - $1,017.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (24)

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