Anna Maria City Vacation Rentals
90 properties available
Welcome to Absolutely Anna, a charming two-bedroom, two-bathroom vacation home with a private pool, cabana lounge, and screened-in porch, just a two-minute walk to Bean Point Beach. This dog-friendly Anna Maria Island rental is the perfect mix of coastal comfort and fun extras like foosball, outdoor TV, and a beach wagon to make your island getaway
Social Nest by Anna Maria Island Accommodations Welcome to Social Nest, a charming three-bedroom, two-bath vacation home perfectly located on iconic Pine Avenue in the city of Anna Maria. This home is located directly above the popular Pizza Social shop right on Pine Avenue in the city of Anna Maria. This inviting island retreat features a private
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Blissful Bay at Bayside Bungalow by AMI Locals Vacation Rental License #VR18-000088 Welcome to Blissful Bay at Bayside Bungalow, a bright and beachy three bedroom, two bath condo perfectly located on the north end of Anna Maria Island! Just across the street from the Tampa Bay and near the islands pristine white-sand beaches, this retreat blends co
Silver King by Anna Maria Island Accommodations VR16-000118 Welcome to Silver King, a stunning four-bedroom, three-bathroom canal-front vacation home with a bonus bunk room, rooftop deck, and a backyard designed for endless fun. Located just four blocks from the Gulf beaches and three blocks from the charming shops and dining on Pine Avenue, this l
High Tide Haven by Anna Maria Island Accommodations Welcome to High Tide Haven, a newly renovated three-bedroom, two-bathroom vacation home in the heart of Anna Maria City. Just two blocks from the Gulf beaches and steps from the boutiques and restaurants of Pine Avenue, this elevated villa offers a private heated pool, multiple balconies, and brig
Siena Sky by Anna Maria Island Accommodations Welcome to Siena Sky, a four-bedroom, four-bath luxury vacation home just steps from the beach. This stunning island getaway combines modern elegance with relaxed coastal comfort, featuring a rooftop deck with Gulf views, a heated pool and spa, and a prime location within walking distance of Pine Avenue
Hammock Dreams by Anna Maria Island Accommodations VR16-000408 Welcome to Hammock Dreams! Escape to the peaceful island lifestyle at Hammock Dreams, a stunning canal-front home nestled in the heart of Anna Maria. With three bedrooms, two bathrooms, and a private pool, this tropical retreat is ideal for families or small groups seeking the perfect
Sand and Sea 113 B by Anna Maria Island Accommodations VR16-000423 Welcome to Sand and Sea 113 B, a cozy two-bedroom, one-bath ground-level condo just a one-minute walk from Anna Maria Beach and two blocks from Pine Avenue. Perfect for couples or small families, this Anna Maria Island accommodation offers a private patio, shared pool, and all the c
Tiny Tides by Anna Maria Island AccommodationsWelcome to Tiny Tides, a cozy and recently refreshed cottage-style getaway tucked in the heart of Anna Maria. This two-bedroom, one-bath home is perfect for couples or small families looking for a comfortable, budget-friendly place to stay while enjoying everything the island has to offer. You’ll love b
Coconut Breeze Estate by Anna Maria Island Accommodations Home in Anna Maria, FloridaEscape to Coconut Breeze Estate, your ultimate four-bedroom, four-bathroom retreat on Anna Maria Island! Nestled on the highly desirable northern end, this stunning home is just a five-minute walk from the pristine beaches at Bean Point. Located near Pine Avenue’s
Shore's Nice by Anna Maria Island Accommodations VR21-000020 Experience your ultimate Florida escape at Shore's Nice, a charming two-bedroom, two-bath vacation home located just steps from Bayfront Park Beaches! Perfect for families or small groups seeking tranquility and coastal beauty, this bright retreat is less than three minutes from Pine A
Hip Nautic by AMI Locals Vacation Rental License #VR22-000090 Welcome to Hip Nautic, a luxury four bedroom, four and a half bath beach retreat just steps from the beautiful bayside shores of Anna Maria Island. Perfectly situated near Pine Avenue’s shopping and dining, this modern, pet-friendly home offers upscale amenities including a private pool
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