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
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
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
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 June
From $1,450 /Week
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
A Lazy River Day and Night 4 Bedroom Custom Pool home on Anna Maria Island
OFFER
A Lazy River Day and Night 4 Bedroom Custom Pool home on Anna Maria Island
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 4 , Sleeps: 8
A flexible home with 4 bedrooms 3 1/2 baths that can separated for different generations of families or friends traveling together.
From $2,800 /Week
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

OFFER May Prices Reduced!

Special offer period: Apr 30, 2021 - Jun 27, 2021

One-of-a-Kind 33 Luxury Beach House on the desirable North End of Anna Maria!
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 3 , Sleeps: 6
Come relax and enjoy this stunning retreat with a modern, clean beach style ambiance. The white sandy beaches of Bean Point are only a 5 minute stroll away!
From $448 /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
Newly Remodeled 3bed2bath Cottage - No Streets to Cross to Beautiful Beaches
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 3 , Sleeps: 6
Anna Maria Aloha is a completely remodeled 3 bedroom 2 bathroom Cottage steps to the beach with no streets to cross!
From $208 /Night
Renovated 22 Cottage North End-Steps to Beach Tropical LandscapingHeated Jetted Pool
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 2 , Sleeps: 4
SURF’S UP has been completely and lovingly renovated from top to bottom and is gorgeously decorated!
From $291 /Night
Beautiful 4-BR, Very Close to Gulf Beach, LARGE Heated Pool
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 7
House, 4 Bedrooms, 2.5 Baths (Sleeps 7)
From $400 /Night
The Happy Hibiscus Island Oasis with Ocean Views
South West FL > Anna Maria Island
House , Bedroom(s): 4 , Sleeps: 8
The perfect getaway with a pool and hot tub, putting green, pool table, foosball table and more fun!
From $1,000 /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 $269 /Night
Playa Encantada, Steps to the Beach
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 $156 /Night
North End Luxury Beach Cottage STEPS TO THE BEACH Heated Pool and Outdoor Living Area
South West FL > Anna Maria Island > Anna Maria
Cottage , Bedroom(s): 2 , Sleeps: 4
Seahorse Cottage is one of our most popular properties located on the desirable North End of Anna Maria with a Heated Pool and Outdoor Living Area
From $291 /Night
Elegant Southern 4 bed pool home
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 4 , Sleeps: 8
4 beds, 2.5 baths, private pool
From $350 /Night
Secluded Bungalow on Historic Pine Ave
South West FL > Anna Maria Island > Anna Maria
Bungalow , Bedroom(s): 2 , Sleeps: 4
Secluded Location on Anna Maria Islands' North End! Tucked away along Anna Maria Island's historic Pine Avenue
From $147 /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.
22 North End Beach House near Bean Point Beach!!
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 2 , Sleeps: 4
Located on the desirable North end of Anna Maria Island just steps away from the famous Bean Point Beach, Rod N Reel Pier and Bayfront Park!
From $269 /Night
CHARMING HOUSE W HEATED POOL, STEPS TO BEAN POINT BEACH, PINE AVE, DINNING, AND SHOPPING
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 2 , Sleeps: 4
Charming two story duplex- each unit 2bed/1 bath. Rent 1 unit or both. Perfect for an extended family/ friends who want their own place but still be together.
From $182 /Night
Palm Perch...the perfect island getaway!
South West FL > Anna Maria Island > Holmes Beach
Apartment , Bedroom(s): 2 , Sleeps: 4
Palm Perch... Newly renovated unit close to beach, shopping & restaurants
From $225 /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
Sea Glass on Park - Premier Luxury on Beautiful Park Ave! Steps to Beach, Pool, Spa
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
Luxurious High End 4 Bed 3 1/2 Bath Home in Anna Maria, Pool/Spa, Beach Gear
New Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point & Pine Ave
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
4 Bed 4 Bath House, Sleeps 8