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$10,470
$10,470
Available: Right Now
You'll fall in love with Diamond Surf's “Old Florida” charm and feel. Our private ground level home means no stairs to climb.Diamond Surf is perfect for families, couples or a small group of friends. The house is located with an easy 3-minute str...
$10,050
$10,050
Available: Right Now
Boathouse Cottage is on the west side of the duplex on the quiet street of Gladiolus on north end of Anna Maria. Removed from the condos, hotels, and crowds.We are one short block from sunrises on the bay, and the historic Rod and Reel Pier. Two ...
$11,340
$11,340
Available: Right Now
Welcome to Beach N Bay 206! PoolCOOLINGfor hot summer days!A honeymooners delight or a couple’s retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Ma...
$10,800
$10,800
Available: Right Now
** Ask about last minute deals !A contemporary aesthetic combined with a top-notch location is sure to make Pelican Bay a favorite part of your Anna Maria vacation!Tucked away at the north end of the Island just a bit beyond the shops ...
$12,960
$12,960
Available: Right Now
Welcome to Casa Posada!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Historic ground floor cottage but with all new interior paint and furn...
$11,880
$11,880
Available: Right Now
Our highly rated vacation rental home is private, immaculately clean, whimsically decorated, professionally landscaped, and boasts one of the larger private pools, larger backyards, and larger 2+ bedroom homes on the Island. The spa is accented by ir...