Anna Maria Island Vacation Rentals With a Pool
91 properties available
Castaway Cottage by Anna Maria Vacations Home in Holmes Beach, Florida VRC17-000189 Welcome to Castaway Cottage, a three bedroom, two bath vacation home with a private pool, game room, and plenty of family-friendly amenities! Located less than a 10-minute walk to the white sand Gulf beaches, this Holmes Beach retreat is also close to shops, restau
Gulfside Oasis by Anna Maria Vacations Home in Holmes Beach, Florida Escape to Gulfside Oasis, a stunning multi-level vacation home just seconds from Anna Maria Island’s breathtaking Gulf beaches! Offering six spacious bedrooms and five bathrooms, this luxury retreat features a private outdoor entertainment area, a game room with ping pong and foos
Sunshine Reef by Anna Maria Vacations Home in Anna Maria, FL VR16-000425Experience the perfect family getaway at Sunshine Reef, a beautifully updated four-bedroom, four-bathroom ground-level home nestled in the prestigious north end of Anna Maria Island. Recently refreshed with new kitchen and bathroom updates, this home is showcased with current p
Stay Calm by Anna Maria Vacations Home in Holmes Beach, Florida VPR16-000304 Welcome to Stay Calm, a beautiful ground-level vacation rental nestled just five minutes from Anna Maria Island’s white sandy beaches! This spacious three-bedroom, two-bath home offers a private sparkling pool, a screened-in lanai, and a covered patio perfect for family
Egrets Nest by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000610 Welcome to Egrets Nest, a beautiful coastal paradise just six minutes from the sparkling white sands of Holmes Beach! This four-bedroom, two and a half bath home features a lush backyard lined with Florida greenery, a private pool with an in-water sundeck, and a spac
Beachfront Bungalow by AMI Locals Vacation Rental License #VRC19-000270 Welcome to Beachfront Bungalow, a rare four-bedroom, three and a half bath coastal cottage located directly on the sandy shores of Holmes Beach on Anna Maria Island! With nothing but your private pool and spa between you and the Gulf, this beachfront escape is designed for trav
Big Nauti by Exclusive Vacations TPL22-000071, DWE5105909Welcome to Big Nauti, an extraordinary eight bedroom, eight and a half bath luxury waterfront home that redefines Anna Maria Island living. Located directly on the Bay in Bradenton Beach, this stunning retreat pairs breathtaking panoramic views with resort amenities, including a rooftop deck,
Sweet Caroline by Exclusive Vacations Vacation Rental License #VR23-000009 Welcome to Sweet Caroline, part of our Exclusive Collection. This luxury four bedroom, four and a half bath Anna Maria Island vacation home just one small block from the Gulf beaches. This coastal retreat blends refined design, resort-style amenities, and a relaxed island vi
Oceanfront Paradise by AMI Locals TPL25-000069, DWE5105909Welcome to Oceanfront Paradise by AMI Locals, a spectacular five bedroom, five full and two half bath beachfront home perfectly positioned along the white sands of Bradenton Beach on Anna Maria Island. Designed for ultimate relaxation and entertainment, this luxury getaway offers direct beac
Beach Escape by AMI Locals Vacation Rental License #VR18-000090 Welcome to Beach Escape, a stunning five-bedroom, four-bath luxury home just one street from the powdery white sands of Anna Maria Island. Ideally located on the peaceful north end near Bean Point Beach, this coastal retreat combines upscale comfort with endless outdoor fun. Spend your
Twisted Turtle (Formerly Known As Peachy Keen) by AMI Locals VPR22-000026 Escape to Twisted Turtle, a luxurious family vacation rental on Anna Maria Island! This spacious three-bedroom, plus loft, home is just 200 steps from the Gulf, offering stunning water views and easy access to the island’s best amenities. Wake up to breathtaking sunsets, spl
Dolphin House by Anna Maria Vacations Duplex in Holmes Beach, FloridaVRC16-000338Experience the tropical charm and luxury of Dolphin House, a beautiful three-bedroom, two-and-a-half-bath townhome just a six-minute walk from the beach in Holmes Beach! This stunning home features a brand-new sparkling pool with a gorgeous waterfall, a covered patio w
