Vacation Rentals

100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.


Properties Available 34 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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated Pool​Hur
Hot HOT 26
Anna Maria Island Beach Waves
2 BR 2BA Condo
$187.00 - $662.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (23)
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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolAnna
Hot HOT 50
Anna Maria Island Beach Palace
4BR 3BA House
$382.00 - $1,483.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (66)
Relax on the screened-in Balcony overlooking sparkling waters of Palma Sola Bay. Palm fronds rustle in sea breeze, a great egret takes flight into an azure sky. Perico Bay Club is a nature-lovers paradise! This 2BR/2BA luxury condo is a short walk or bike ride from three nature preserves; the Robinson Preserve, the Neal Preserve, and Perico Preserv
Hot HOT 20
Perico Coastal Bay
2 BR 2BA Condo
$119.00 - $617.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.​Hurricane Update:The entire complex is built on pillars more than 20 fe
Hot HOT 20
Anna Maria Island Beach Bay Breeze
2 BR 2BA Condo
$140.00 - $472.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (8)
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 20
Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants
2 BR 2BA Condo
$191.00 - $668.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.8 (8)
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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolGulf
Hot HOT 26
Absolute Anna Maria-Private Beach Access-Heated Pool-Water Views From Every Room
2 BR 2BA Condo
$187.00 - $699.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.9 (23)
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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated Pool​Hur
Hot HOT 31
Gulf Breeze Ami-2BD-2BA-Condo-Private Beach Access-Heater Pool-Water Views From Every Window
2 BR 2BA Condo
$149.00 - $492.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated Pool​Hur
Hot HOT 26
Anna Maria Island Beach Palms 5B
2 BR 2BA Condo
$173.00 - $591.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (24)
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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated Pool​Hur
Hot HOT 24
Anna Maria Island Beach Palms 7A
2 BR 2BA Condo
$143.00 - $473.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (29)
​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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolHur
Anna Maria Island Beach View 207
2 BR 2BA Condo
$140.00 - $472.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (18)
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 PoolWelcome
Hot HOT 41
Anna Maria Island Blue Bella Bliss - Private Heated Pool
Holmes Beach
$7,000.00 - $19,866.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 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!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolHur
Anna Maria Island Beach View 208
2 BR 2BA Condo
$133.00 - $449.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.7 (9)

Tell us what you're looking for and someone will contact you with available options.

I agree