Two Bedroom Vacation Rentals
Our collection of 2 bedroom homes on Anna Maria Island is thoughtfully curated for couples, small families, and relaxed coastal getaways. These homes offer a seamless blend of comfort and style, with inviting interiors, private outdoor spaces, and convenient access to the island’s beautiful beaches.
Whether you’re planning a quiet escape or a laid-back stay near the water, each property is designed to deliver a refined, easygoing experience that feels distinctly Anna Maria Island.
11 properties available
Welcome to L'Oasis West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Your own private island oasis, just four blocks from the white-sand beaches of Anna Maria Island.L’Oasis West is a charming two-bedroom, two-bath retreat designed f
Welcome to Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover Cozy Cabana East, where comfort, care, and connection come together in a thoughtfully designed, single-level home just a short walk from the beach. Blending
Welcome to L'Oasis East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Your own private island oasis, just four blocks from the white-sand beaches of Anna Maria Island.L’Oasis East is a charming two-bedroom, two-bath retreat designed f
Welcome to Island Girl East!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl East which is a completely private unit, but shared backyard pool area with Island Girl West.Please inquire directly for booking both sides together for whole entire private home and pool area as
Welcome to Sunset Margarita!Bradenton, Florida (Just off Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.The SpaceSet within Margaritaville’s One Particular Harbour waterfront community, Sunset Margarita blends modern finishes with easy, resort-style living. This third-f
Welcome to Kokomo!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceDiscover Kokomo, where comfort meets calm in a thoughtfully updated beach cottage just a short walk from the Gulf of Mexico. Designed for rest and reconnection, this home
Welcome to Fins Up!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceYour serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenie
Welcome to The Cottage on Pine!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceStep inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmos
Welcome to Catching Waves!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Catching Waves — where laid-back island living meets everyday adventure. Just a short stroll to the white-sand beaches of Holmes Beach, this ground-level h
Welcome to Cozy Cabana West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Where slow mornings and quiet evenings meet the rhythm of island life.Just a short stroll from Holmes Beach, this thoughtfully designed bungalow invites guests to rest, r
Welcome to Island Girl West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl West*THIS HOME IS RECEIVING A COMPLETE EXTERIOR REFRESH OF BALCONY DECKING, POOL PATIO AREAS AND LANDSCAPING AS WELL AS INTERIOR REFRESH COMING DECEMBER 2026Step inside Island Girl West, where na
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