Vacation Rentals
Cancel 14+ days before arrival for a 100% refund or 7-13 days before for a 50% refund.
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% refundHurricane 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 - $513.00 / per night
2
bedrooms
2
baths
6
guests
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 PoolWelcome
Anna Maria Island Blue Bella Bliss - Private Heated Pool
Holmes Beach
$289.00 - $1,387.00 / per night
5
bedrooms
3
baths
10
guests
The fourth bedroom is located in the adjoining cottage. This property has a maximum occupancy of eight people including the adjoining cottage. Violation of this policy will result in immediate eviction without compensation. Welcome to the good life. This custom-built, waterfront, 4bd/4ba island palace is nestled by Bean Point at the north end of An
Anna Maria Beach Serenity
4BR 4BR House
$5,000.00 - $13,925.00 / per night
4
bedrooms
4
baths
8
guests
5
(7)
Steps to the beautiful white sand beach and turquoise waters of the Gulf of Mexico this 2nd floor house is DIRECTLY ON THE BEACH!As you walk out the door and sink your toes into the sand of our award winning beach your perfect Anna Maria Island vacation begins.This Gulf Front house has sliding glass doors and large windows that perfectly frame the
Anna Maria Island Beach Watch
1BD 1BR
$2,110.00 - $7,174.00 / per night
1
bedrooms
1
baths
4
guests
4.6
(5)
Welcome to Cottage Haven! This charming cottage located in Bradenton Beach is a very short walk to the beautiful white sand beaches. Featuring its own private backyard you can sit back and unwind on one of the loungers as you enjoy a home-cooked meal from the propane grill. The ground level home is nicely decorated and exudes a sunny, quaint “Old F
Cottage Haven-One Minute Walk To The Beach-Private Yards-Keyless Locks
2BR 2 BR Cottage
$3,000.00 - $7,169.00 / per night
2
bedrooms
2
baths
5
guests
5
(6)
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 PoolAnna Mar
Anna Maria Island Beach Palace
4BR 3BA House
$407.00 - $1,443.00 / per night
4
bedrooms
3
baths
8
guests
4.9
(66)
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
1BR 1BR Cottage
$3,000.00 - $7,246.00 / per night
1
bedrooms
1
baths
2
guests
4.7
(7)
This sun-drenched 3br/3ba tropical beach cottage centrally located by Holmes Beach in the heart of Anna Maria has been described as one of the “prettiest vacation homes on the island.” This authentic 1947 beach bungalow has been completely (and splendidly!) renovated with raised ceilings, travertine floors, and showers, granite countertops in the k
Anna Maria Island Surfside Bungalow
3BR 3BR House
$4,000.00 - $9,745.00 / per night
3
bedrooms
3
baths
6
guests
4.7
(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 PoolHurrica
Anna Maria Island Bay Watch Bungalow
2 BR 2BA Condo
$174.00 - $627.00 / per night
2
bedrooms
2
baths
5
guests
4.8
(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!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
Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach
2 BR 2 1/2 BA Condo
$157.00 - $529.00 / per night
2
bedrooms
2
baths
6
guests
5
(9)
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 PoolHurrican
Bradenton Beach Club Bliss-3 Bedroom-2 Bathroom Condo-2 Pools-HotTub-Private Beach Access
3 BR - 2BR Condo
$176.00 - $705.00 / per night
3
bedrooms
2
baths
6
guests
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!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 Beach Palms 2A
2 BR 2BA Condo
$143.00 - $516.00 / per night
2
bedrooms
2
baths
6
guests
5
(28)
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