Vacation Rentals

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
Anna Maria Island Paradise❤️Close to beach, shops&restaurants, heated pool, private lanai!
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Book a relaxing vacation at our condo, situated in a private complex on the beautiful Anna Maria Island, only a short walk to the beach, shops and restaurants!
From $700 /Week
Sirenia By The Sea - Waterfront Pool Hot Tub Dock Sauna - Steps to the Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 5 , Sleeps: 12
Picture yourself vacationing in a huge 5 Bedroom luxurious tropical villa, the perfect Anna Maria Vacation Rental for large groups
From $1,999 /Week
AMI Waterfront Beach Condo w Pool!
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Watch sunrise over the bay, walk across the street to enjoy the beach. Restaurants & shopping all within walking distance! - Anna Maria Island Vacation Rentals
From $1,250 /Week
Sirenia Beach House  Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
OFFER
Sirenia Beach House Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 10
Sirenia Beach House ~ Beach Resort Style Luxury - Waterfront - Dock - Htd Pool - Spa - Backyard Beach - Tiki Hut - Hammock and more!
From $1,799 /Week

OFFER May 1 - 8, 2021 OR May 8 - 15, 2021 - Special Discounted Rate $3,099/week plus fees and taxes

Special offer period: Feb 4, 2021 - May 1, 2021

Anna Belle - Waterfront Luxury Home: North End wDock, Pool, Spa, Screened Lanai, Free WiFi
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 8
Ground level living, 3 bedrooms, 2 baths, sleeps 8. Private Home with Waterfront Dock, Pool, Hot Tub, Wifi - Anna Maria Island Vacation Rentals
From $700 /Night
SMUGGLER'S COVE RESORT - Anna Maria Island Vacation Rentals
South West FL > Anna Maria Island
Condo , Bedroom(s): 1 , Sleeps: 4
Quiet family friendly resort with access to the Bay and the Gulf
From $130 /Night
Sirenia Cove - Htd Pool Waterfront Dock Ping Pong Outdoor Bar Backyard Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 10
Sirenia Cove is the perfect vacation home to nature lovers. Located directly on the waterfront, you are perched on a prime location to enjoy everything.
From $1,799 /Week
Sunkissed & Salty: Dreamy Amenities. Prime Location. Available Beginning May 15, 2021
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
New Anna Maria Vacation Rental Home Completing 5/2/2021 4 Bed; 4 Bath, Pool & Spa, Putting Green, Cornhole, Game-room. 1.5 minutes walk to beach. Gulf Views
From $525 /Night
APRIL 24TH - MAY 1ST PRICE HAS BEEN SLASHED!! COME SOAK UP THE SUN ON ANNA MARIA ISLAND!!
OFFER
APRIL 24TH - MAY 1ST PRICE HAS BEEN SLASHED!! COME SOAK UP THE SUN ON ANNA MARIA ISLAND!!
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 $250 /Night

OFFER April Special Deal - $260/night April 24 - May 1!!

Special offer period: Apr 24, 2021 - May 1, 2021

Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
OFFER
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
Gorgeous AMI Villa with private pool & just steps to the beach!
South West FL > Anna Maria Island > Holmes Beach
Villa , Bedroom(s): 3 , Sleeps: 8
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
Affordable Rates on Anna Maria Island!
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 4
Beautiful Condo on Anna Maria Island!
From $99 /Night
Edge of Paradise at Margaritaville - 5 Night Min
South West FL > Anna Maria Island
Condo , Bedroom(s): 3 , Sleeps: 8
Luxe Condo I Resort Amenities I Near Anna Maria Island I Margaritaville - Anna Maria Island Vacation Rentals
From $170 /Night
Anna Maria Island Beach Front
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 4
Anna Maria Island Tiffany Place Beautiful Views, Perfect Location, Free Trolley, 2 Bedroom, 2 bath, Beach Front, Extra Large Balcony, heated pool
From $180 /Night
Casa Gucci - Anna Maria Island Vacation Rental
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
NEW! Updated Condo on Anna Maria Island!
From $1,050 /Week
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
The Anna Maria Island Beach Palms 2B
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 4
FAMILY/CHILD FRIENDLY CONDOMINIUM.
From $121 /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
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
The Anna Maria Island Beach View 208
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 4
FAMILY/CHILD 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 Sands 203
South West FL > Anna Maria Island
Condo , Bedroom(s): 2 , Sleeps: 5
The Anna Maria Island Beach Retreat, 2 bedrooms, 1 bathroom, sleeps 6 maximum
From $152 /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
The Lighthouse
South West FL > Anna Maria Island
House , Bedroom(s): 3 , Sleeps: 6
Unique Lighthouse 3 Beds, 2.5 Baths, Pool. Short walk to beach
From $300 /Night