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Cheerful Serenity – Luxury Waterfront Oasis on Perico Bayou with Pool, Dock & Sunset ViewsWelcome to Cheerful Serenity, a cheerful 3 bedroom, 2 bathroom waterfront escape with unforgettable sunset views over Perico Bayou. This serene cul-de-sac location feels worlds away yet keeps you close...
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Had a wonderful stay. The layout is beautiful, relaxing amenities, thoughtful details throughout the property, made our stay truly relaxing. The location is fantastic. The home is in a wonderful quiet neighborhood...
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Kingfisher Cay is a newly renovated, beautifully designed, property boasting an outdoor covered patio, heated pool, and a games area with tiki hut, life sized connect four and corn hole. The one story bungalow has three bedrooms; one king, one queen, and one room with two twin beds. All bedrooms have...
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The house and entire property was beautiful. It had everything you could wish for and more. It was spotless. We hope to stay again next year. Thank you for sharing your slice of paradise.
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NEW LISTING! Welcome to Bay Dream Believer, your luxurious bayfront escape on beautiful Longboat Key! This bright and beautifully upgraded condo offers breathtaking views of Sarasota Bay through massive picture windows and an enclosed patio that lets you soak in the scenery year-round. Located just across...
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Great location on Longboat Key…out of the crowds with great beaches. Windward Bay where this is located, is a lovely larger condominium community with excellent amenities. The pickleball group is awesome....
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Waterfront Paradise Awaits at Marina Walk!Discover the ultimate coastal escape in this stunning 3-bedroom, 3-bathroom waterfront gem, nestled in the exclusive gated community of Marina Walk at Jimmy Buffet's One Particular Harbor. Perico Island's sought-after retreat is just 1.8 miles from...
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We had such a fantastic, relaxing holiday staying at Marina Walk. Jeff and Shandra are amazing, super responsive, and they made us feel welcome and at home. The views from our condo over the bay were out...
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Tucked away in sought-after Northwest Bradenton, this cheerful canal-front retreat is all about easy Florida living—where sunny days, calm waters, and laid-back coastal vibes come together. With a private dock, direct Gulf access, and peaceful water views right out back, it’s the perfect spot...
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What an amazing house! Fully equipped with everything my family of 5 needed. Perfect location for beaches, shops, and restaurants. The pool is wonderful, and the putting green is a great little fun bonus....
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As seen on Staycation! Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof,...
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Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....
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Welcome to The Cheerful Pelican – Your Perfect Beach-to-Bay Getaway!Discover the ultimate escape in this charming 2-bedroom, 2-bathroom retreat, perfectly nestled between the stunning Gulf beaches and tranquil bay waters. The Cheerful Pelican offers the best of both worlds with sunrise views...
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My wife and I had a wonderful 3 week stay in paradise It was a pleasure to book with the Cheerful Pelican and working with Jeff and Shandra. They kept us informed and helped us work through the booking...
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This 1 BR, four-guest, condo strategically placed within short walks to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) will keep you CHEERFUL your entire stay! Coastal amenities: new King Bed (not pictured), front screened lanai, heated...
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Escape to your luxurious coastal retreat overlooking the shimmering waters of Palma Sola Bay. This coveted 3rd-floor, 3 bedroom, 2.5 bathroom, turnkey-furnished condo offers the perfect blend of comfort, style, and serenity, with two private balconies capturing sunrise over the pond and golden Gulf sunsets...
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Enjoy Cheerful coastal living in this beautifully furnished 3-bedroom, 3-bathroom monthly rental in the highly desirable Waterway Condominiums. Ideally located less than 3 miles from the sugar-white sands of Anna Maria Island, this spacious waterfront residence offers the perfect combination of comfort,...
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This 1 BR, four-guest condo is perfectly located within walking distance to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) to keep you CHEERFUL your entire stay!Coastal amenities: front screened lanai, heated pool, beach toy closet (including...
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Luxurious Waterfront Living with Resort-Style Amenities: Recently Renovated 2 Bed, 2 Bath Condo with BOAT LIFT in West Bradenton on the south side of Palma Sola Bay just UNDER 3 MILES TO ANNA MARIA ISLAND! Experience breathtaking tropical canal views from your SCREENED LANAI, and walk the sea wall to...
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NEW TO THE MARKET! Escape to a refined coastal retreat near the tranquil waters of Palma Sola Bay. This desirable 3rd-floor, 3-bedroom, 2.5-bathroom, turnkey-furnished condo offers relaxed luxury and serene surroundings, with two private balconies ideal for enjoying soft morning light and warm Gulf Coast...
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Welcome to Cheerful Oasis – Your Bay-to-Beach Escape!Discover the ultimate island retreat at Cheerful Oasis, a delightful 2-bedroom, 2-bathroom condo perfectly situated for your next getaway. Nestled just off the walking trail to the Marina, Bridge Street, and Bradenton Beach, this serene haven...
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Welcome to Martinique Cheer, your cheerful beachside escape on beautiful Anna Maria Island! This rare higher-rise Holmes Beach condo offers incredible Gulf views and a prime location in a quiet, well-maintained complex. Just steps from the sand and a short stroll to the heart of Holmes Beach, you’ll...
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NEW MANAGEMENT! Spend your days at the beach, your afternoons by the pool, and your evenings unwinding at Cheerful North Beach Getaway — a peaceful island villa just a three-minute walk from the soft white sands of the Gulf in Holmes Beach on Anna Maria Island.This freshly renovated 2-bedroom,...
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Enjoy peaceful waterfront living in this comfortable and spacious 2-bedroom, 2-bath waterfront condo located on the south side of Palma Sola Bay—just under 3 miles to Anna Maria Island’s beaches! Relax on your screened lanai and take in tranquil canal views with frequent manatee and bird sightings.The...
Featured review
Thank you to Cheerful Rentals for arranging this beautiful spot for me to stay for the winter in Bradenton Florida. The accommodations was everything that was described plus more! Clean, beautifully decorated,...
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NEW MANAGEMENT! Welcome to Triple Palm Paradise, your private waterfront escape in the sought-after San Remo Shores community of West Bradenton. Whether you're bringing your boat, spending your days on Anna Maria Island, or simply looking for a relaxing Florida retreat, this beautifully appointed...
