Vacation Rentals

Gorgeous AMI Villa with private pool & just steps to the beach!
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 3 , Sleeps: 6
Welcome to AMI Villa! When you come to Anna Maria Island, make this charming Mediterranean 3 bed & 3 bath villa with a private pool your home away from home!
From $300 /Night
Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
The Blue Heron is a beautiful 4 bedroom 3.5 bath brand new luxury home on Anna Maria Island for rent - Anna Maria Island Vacation Rentals
From $480 /Night
The Veranda on Jacaranda - Luxury Home, North Anna Maria Island across from Bean Point
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 8
Newer 3 story Home and beautifully decorated. Elevator to access all floors. Garage parking, private fenced yard, heated pool, beach gear, 6 Bikes, Ocean views.
From $350 /Night
SeaDuction - 400 Steps to Beach!
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
2 Bed, 2 Bath Condo on Holmes Beach - 400 steps to the beach Professional pictures coming end of July
From $1,275 /Week
SMUGGLER'S COVE RESORT - Anna Maria Island Vacation Rentals
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 1 , Sleeps: 4
Quiet family friendly resort with access to the Bay and the Gulf
From $130 /Night
Bayberry Cottage South - Pool
South West FL > Anna Maria Island > Bradenton Beach
House , Bedroom(s): 2 , Sleeps: 6
Walk to the beach or laze by the backyard pool! Or jump on the free island trolley and see the sights.
From $300 /Night
Bayberry Cottage North - Pool
South West FL > Anna Maria Island > Bradenton Beach
House , Bedroom(s): 2 , Sleeps: 6
2 bedrooms, 1.5 baths, private pool, walk to the beach!
From $300 /Night
Direct Beachfront Anna Maria Island Condo Rental
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 1 , Sleeps: 4
Walk out your door and onto the beach on beautiful Anna Maria Island!
From $250 /Night
Anna Maria Island Retreat
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $153 /Night
New Luxury Custom Built Home on North End - Steps to Beach - Heated Pool - Outdoor Kitchen
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 6
Luxury Custom Home on Desirable North End of Anna Maria Island w/Outdoor Kitchen and Heated Pool!! North End Escape is a 2,300 sq. ft.
From $520 /Night
The Anna Maria Island Beach View 207
South West FL > Anna Maria Island
Condo , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $121 /Night
Beach Cottage only steps to the white sandy beaches of Anna Maria Island!
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 2 , Sleeps: 6
Beach Basket is a vintage 1920's cottage located on Oak Ave which dead ends to the white sandy beaches and emerald waters of Anna Maria Island!
From $336 /Night
July 31-AUGUST 7 AVAILABLE - BOOK YOUR ANNA MARIA ISLAND SUMMER VACATION NOW!
OFFER
July 31-AUGUST 7 AVAILABLE - BOOK YOUR ANNA MARIA ISLAND SUMMER VACATION NOW!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Blue Turtle Cottage Anna Maria Island has a sparkling private pool in a tropical backyard and is just steps (Less than 100!) to the white sand beach!
From $315 /Night
Beach Bay Breeze
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $108 /Night
The Anna Maria Island Beach Castaway 2
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $101 /Night
The Anna Maria Island Beach Palace
South West FL > Anna Maria Island
House , Bedroom(s): 4 , Sleeps: 8
Welcome to paradise
From $278 /Night
The Anna Maria Island Beach Castle
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $152 /Night
Bay Watch Bungalow
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
Bay Watch Bungalow: Water Views from Every Room & Upgrades Galore
From $118 /Night
FALL SPECIAL STAY 14 Nights PAY for 12 Nights
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 4
Located in the sought after complex of Playa Encantada; Shell Game is a tropical beach front community on the white sandy beaches of Anna Maria Island!
From $176 /Night
The Anna Maria Island Beach Palms 5B
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $121 /Night
Edge of Paradise at Margaritaville - 5 Night Min
OFFER
Edge of Paradise at Margaritaville - 5 Night Min
South West FL > Anna Maria Island
Condo , Bedroom(s): 3 , Sleeps: 7
Luxe Condo I Resort Amenities I Near Anna Maria Island I Margaritaville - Anna Maria Island Vacation Rentals
From $170 /Night
Anna Maria Island Beach Sands
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $162 /Night
Absolute Anna Maria - Anna Maria Island Vacation Rentals
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 5
WELCOME TO OUR FAMILY FRIENDLY CONDOMINIUM
From $131 /Night
The Anna Maria Island Beach Castaway 1
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $101 /Night
The Anna Maria Island Beach Palms 6B
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 6
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!!
From $111 /Night