Vacation Rentals

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
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
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
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
Coral Castle - Waterfront! 3 Min Walk To Beach!
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 5 , Sleeps: 10
5 bedrooms, 3.5 baths, max. 10 guests, max. 5 vehicles
From $3,850 /Week
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
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
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
PRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL
South West FL > Anna Maria Island > Bradenton Beach
Condo , Bedroom(s): 2 , Sleeps: 4
LUXURY CONDO 2 Bed 2 Bath * SEE SUNSET FROM LANAI * WALK TO SHOPS/RESTAURANTS
From $171 /Night
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
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
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
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
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
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
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.
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
Professionally Decorated Pool Home Just Steps To The Beach
South West FL > Anna Maria Island > Holmes Beach
House , Bedroom(s): 3 , Sleeps: 6
Debby's Place is sure to please! Just 2/10 of a mile from the white sandy beaches and the beautiful waters of Anna Maria Island.
From $240 /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
Sunkissed & Salty: Dreamy Amenities. Prime Location. Steps to Beach
South West FL > Anna Maria Island > Anna Maria
House , Bedroom(s): 4 , Sleeps: 8
New 4 Bed; 4 Bath, Pool & Spa, Putting Green, Cornhole, Game-room and more! 1.5 minute walk to beach. Limited Gulf view
From $530 /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
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
Work From Here! Large Luxury Home w Elevator! Heated Pool & Spa. 3 min walk to Beach!!
South West FL > Anna Maria Island > Bradenton Beach
House , Bedroom(s): 5 , Sleeps: 12
August Availablity Disinfected Large Luxury 5 Bed/5 Bath Home w/ Elevator, Heated Pool & Spa, only 3-minute walk to Beach. Perfect for work & play.
From $699 /Night
Sandy Isle Getaway - Anna Maria Island
South West FL > Anna Maria Island > Holmes Beach
Condo , Bedroom(s): 2 , Sleeps: 6
Condo, 2 Bedrooms, 2 Baths, 6 Sleeps
Bean Point Charmer! 3 Bedrooms Tropical Pool with Outdoor Lounge
South West FL > Anna Maria Island
House , Bedroom(s): 3 , Sleeps: 8
Perfectly situated on the north end of the island, Bay Bungalow, is just a short stroll away from the Rod and Reel Pier, Bay beaches, and famous Bean Point!
From $259 /Night