Vacation Rentals With Pool

62 properties available

Welcome to "Spring Break"! This property is located on the North end of the Anna Maria Island and has a wonderful private, heated pool. Conveniently close to the beach to enjoy the sunset view from the front porch and a short walk of 176 yards to the white sand of the Gulf of Mexico. Just pass a few homes and stick your toes in the water or dine at

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Welcome to Island Priva-Sea! If it is privacy, you are looking for you will get plenty in this North-end Island house. Tucked away in a cul-de-sac the location North of Pine Ave and a peaceful canal front setting make this beautiful home a perfect vacation getaway! Island Priva-Sea has a convenient ground level layout and accommodates up to 6 guest

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Welcome to 1 Step Closer! This beautifully renovated duplex is only a short five-minute walk to the beach. 1 Step Closer is finished in a beach style with hardwood flooring throughout with custom cabinets & granite counter tops. This two-bedroom, two-bath elevated property is just like home, modernly furnished with all the bells & whistles. It slee

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Welcome to The Villas in Holmes Beach! Vacation made easy in this small, private condo setting! Villa 2A is a luxurious one-bedroom villa with updated kitchen and many extras just steps to the beach! It is one of six units and features newly renovated ground level Island living. The property is located just across from the white sandy beaches and t

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What an unforgettable view at Port Royale! This vacation rental is located on Key Royale, a very sought-after neighborhood linked to Anna Maria Island. You will love this canal front home just over the small bridge on Key Royale Drive overlooking Bimini Bay. This beautiful home with designer features is well appointed with 230 feet of waterfront. A

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Welcome to Gulf Sands, a beachfront getaway with stunning views! Gulf Sands 108 condo is a beautiful two-bedroom, two-bath condo that is located directly on the Gulf of Mexico. Offering picturesque views of the white sugar sand and turquoise water, a shared heated pool and an open balcony overlooking the beach! Simply sit back, relax, and enjoy the

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The Westbay Point and Moorings complex is tucked away on the Bay side of the Island and a very sought-after neighborhood to escape the cold North! The condo 214 is a lovely 2-bedroom property with a canal view and with access to a heated pool, hot tub, and tennis courts. Enjoy the open floor plan with updated kitchen and a dining table that sits si

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West Bay Point Moorings 214

Welcome to Pier to Pier Paradise! This beautiful newer luxury home is one of a kind! Three stories high and ideally situated on Anna Maria's North end, the property is tucked into a quiet little neighborhood across the street from the beach and a short walk from the Rod and Reel pier, the city pier, and Pine Avenue. Professionally decorated with av

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Pier To Pier Paradise

Gulf Watch 112 is a completely updated 2-bedroom 2-bathroom gulf to bay condo located in the Gulf Watch condo community. Gulf Watch is a beautifully maintained complex boasting a sparkling heated pool all-year round. This condo is located in Bradenton Beach and is only a few steps away from the beach, shopping, and dining. HIGHLIGHTS • Waterfront

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Runaway Bay 212 is a fully furnished 1-bedroom, 1-bathroom condominium in the centrally located Runaway Bay community. The Runaway Bay complex is situated in the middle of Bradenton Beach around many shops and restaurants. Runaway Bay also has private beach access available to its residents and guests as well as a private fishing dock and kayak lau

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Welcome to The Beach House! Amazing Northern end, luxury home sitting on the Gulf of Mexico with a pool! Directly on the Gulf of Mexico, north of Pine Avenue on beautiful Anna Maria Island, The Beach House is a spectacular beach retreat. Looking like an Old Florida beach house on the outside, the interior has been remodeled to make a stunning, comf

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Fun N Sun is a second-floor unit in the Runaway Bay community. Enjoy the sights and sounds of this tropical getaway and all the amenities of the Runaway Bay Complex being a shared heated pool, private beach access, a club house with a kitchen and living areas to relax and unwind, also a tennis court, shuffleboard, bocce ball, pickleball, fitness ce

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