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Bay House Retreat by Beach Retreats Vacation Rentals Sarasota Bayfront – Near IMG Academy & Downtown Sarasota 5 Bedrooms | 4 Bathrooms | Sleeps 12 | Heated Saltwater Pool | 2 Private Docks Welcome to Bay House Retreat, a luxurious bayfront escape offering over 4,000 sq. ft. of comfort...
Featured review
Four siblings and their spouses enjoyed this spacious home for a week. Right at the water’s edge, with a great pool and spa, it was like a self-contained resort of its own. The views of sunrise and...
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Top Reasons to Book Sunshine Rays: • Private pool + spa (heated upon request for additional fee) • Fully fenced backyard — pet friendly (fee applies) • Spacious 3BR home with 2 living areas • Peaceful pond views from backyard • Minutes to Anna Maria Island beaches •...
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Top Reasons to Book • Private heated pool + hot tub (complimentary heat) • Pet friendly (up to 2 dogs, fee applies) • Short drive to Anna Maria Island beaches • Fully equipped home with washer/dryer • Beach gear included (chairs + towels) • Quiet, relaxing neighborhood •...
Distance to beach: 10 miles to Siesta Key
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Bradenton Paradise 4BR/2BA HEATED POOL & Mini Putt Welcome to your Bradenton retreat, a spacious 4-bedroom, 2-bathroom home designed for comfort, fun, and family gatherings. Sleeping up to 10 guests, this beautifully maintained property offers modern amenities and a bright, open layout perfect for...
Distance to beach: 12 miles to Anna Maria
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CASA ENCANTADA, THE ESTATE ON THE MANATEE RIVER! Spend your vacation at a private, secluded estate on 200' of open water with tropical landscaping and a beautiful lagoon...
Featured review
Stayed here in November with my family and it was an amazing getaway. Captain Julie accommodated every detail. The pool was amazing.. looks like your in your own tropical oasis... private... beautiful views...
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Distance to beach: 15 miles to Bradenton Beach – about 25 minutes away
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Bradenton 5BR/2BA HEATED POOL & Mini Putt Welcome to your Bradenton retreat, a beautifully updated 5-bedroom, 2-bathroom home designed for fun, relaxation, and comfort. Perfect for families and groups, this spacious getaway features a private pool, a mini putting green, and all the modern amenities...
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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...
Featured review
We HIGHLY recommend Cheerful Rentals Jeff and Shandra Holbrook. You will be thrilled with your choice when you choose a cheerful property. Our family trip started before we actually arrived when we first...
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Top Reasons to Book Popeye’s Pool Paradise: • Private heated pool (complimentary heat) • Brand new furnishings throughout • 2 spacious living areas with Smart TVs • Outdoor oasis with BBQ, TV & lounge space • Fully fenced backyard • Garage stocked with...
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Welcome to Bayside Hideaway! Private screened in Heated or Cooled Pool, Outdoor Seating, Fire Table, BBQ Grill Pool table, Table Tennis, Foosball, 2 Paddleboards, & 2 Kayaks Private Boat Dock, Trailer Parking, Short ride to Sarasota Bay Industrial Ice Maker & Deep Freezer Available Short...
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Welcome to Sunshine Cove located in Bradenton, FL Less than 4 miles to Bradenton Beach & the world-famous beaches of Anna Maria Island Private HEATED pool, firepit, BBQ grill, fenced turf yard & pet-friendly Beach chairs, wagon, and a cooler available Family friendly with pack'n'play...
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Why Guests Love It: -Just minutes to Anna Maria Island’s beaches, shops, and restaurants -Private heated pool with fully fenced yard and plenty of outdoor seating -Bright 3BR/2BA home with open floor plan, perfect for families and friends -Fully stocked kitchen, smart TVs, and beach gear ready...
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NOW until 10/11/25 save 20% on any week or 2 weeks 50% off second week The Lakehouse4 is less than 6 miles from the beaches on Anna Maria Island and about 2 miles to the beaches along the causeway in a quiet residential area close to Robinson Preserve. This sprawling ranch style house has everything...
Featured review
We recently stayed here and were very happy. Beds were very comfortable. The 1 bedroom could use a dresser or a bench to put suitcase on and bedrooms could also use a full length mirror. The pool was...
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Luxury Beach Home • Steps to Sandbar Restaurant • Elevator • Sleeps 10 • Pets Welcome Welcome to Villa Del Sol, a luxury Anna Maria Island vacation rental located just two houses from the beach and steps from the iconic Sandbar Restaurant. With Gulf views, heated swim spa, private...
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Top Reasons Guests Love This Home: FREE Heated Resort-Style Pool – Swim Year-Round Expansive tropical backyard oasis with lawn games & firepit Private game room with ping pong + foosball Chef-inspired kitchen with gas cooktop & oversized island W/ Fully Stocked Kitchen ...
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Top Reasons to Book Sunset Oasis: • Waterfront canal home with private dock for manatee/dolphin viewing • Private pool + hot tub (heated upon request for additional fee) • Kayaks included for guest use • Outdoor fireplace + stunning sunset views • Spacious layout with multiple...
Featured review
The house was very clean and well kept upon arrival. The pool area, outside space, and seawall deck were fantastic. The only slight blemishes were lack of basic kitchen needs like garbage bags, spices pot...
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Top Reasons to Book: - Heated Pool (Free Heat Included) - 4 Bedrooms + Theatre Room – Sleeps Up to 12 - Direct Palma Sola Bay Access with Water Views - 85" OLED Movie Theatre with Surround Sound - Beach Gear Included - Free Beach Setup for 7+ Night Stays Welcome to 11 Palms, a spacious...
Distance to beach: 2 miles to Palma Sola Causeway Park
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⭐ OVERVIEW 4BR / 2BA private home in Bradenton, FL Heated pool & hot tub (complimentary heat included) 3 King Suites + bunk room w/ trundle (family-friendly) Game room with Pac-Man arcade, shuffleboard, cornhole & frisbee golf Outdoor oasis with fire pit, BBQ grill, bar area &...
Featured review
Bill and Heather were very attentive. House was in perfect location to drive to beach, or stay at pool. Upon arrival we had a couple normal issues and Bill and Heather wastes not one minute taking care...
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Top Reasons to Book: - Waterfront Canal Home Near Cortez Bridge - Private Pool/Spa (Additional Fee Applies) - Minutes to Anna Maria Island Beaches - Paddle boards Available for Guest Use - Boat Dock Access (Lift Not for Guest Use) - Pet Friendly (Additional Fee Applies) - Professionally Managed Welcome...
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Your Spring & Summer Waterfront Escape in Bradenton Spring mornings begin gently here. The sun rises over the water, coffee tastes better by the canal, and warm Florida air invites you outside before the day even starts. You may spot manatees drifting past the dock while the family slowly wakes...
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Welcome to Dolphin Cabin! Screened in Private Pool, Sunset Views, Dolphin Activity Short Drive to the World Class Beaches of Anna Maria Island Bring your Boat or other Water Toys! Fully stocked kitchen with BBQ Grill High-speed Wi-Fi, Smart lock for Self-Check-in Welcome to Dolphin Cabin! This...
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Welcome to Mermaid Bay Located in San Remo Shores just off Anna Maria Island! Short drive to the World Class Beaches of Anna Maria Island Private Dock, Bring your Boat or other Water Toys! Enjoy Kayaking, Bike Riding and so much more Private Screened in Heated Pool, Outdoor Seating, BBQ Gas Grill High-speed...
Distance to beach: 5 miles to Holmes Beach
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Our own webpage with instant booking for 2026 and 2027 is ready for you. Ask with inquiry for our specials. Scroll here down and you'll find the link to our webpage next to my photo. The house was completely remodeled in 2024 ! Everything brand new! We have developed a comprehensive Safety...
Featured review
This is a beautiful home in a nice residential area. It is well maintained and has everything you could need for a relaxing vacation in the Florida sun. It is close to the beach and local restaurants. That...
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Elevated Hospitality, Thoughtfully Delivered Experience true white-glove hospitality. Our dedicated team responds within minutes, with hands-on management and a quality inspector ensuring every detail is thoughtfully prepared before you arrive. Throughout your stay, we remain available and attentive...
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NOW until 10/11/25 save 20% on any week or 2 weeks 50% off second week Enjoy the TIKI hut, or the hot tub, swim in the pool or shoot a game of pool. We refer to this home as "The Lakehouse." The property features a TIKI hut on a small lake where one can relax or try a hand at fishing. This...
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Elevated Hospitality, Thoughtfully Delivered Experience true white-glove hospitality. Our dedicated team responds within minutes, with hands-on management and a quality inspector ensuring every detail is thoughtfully prepared before you arrive. Throughout your stay, we remain available and attentive...
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The Sunshine House gives a whole new meaning to fun in the sun. From the moment you step inside you are greeted by by sunshine with a beautiful mural. Each room greets you with it's own flair of bringing the sunshine in. And the back yard is set up to make you forget you came to see our beautiful...
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Escape the business of the holiday and slow everything down at the Sandpiper. This is the place to reconnect and make memories that truly matter. Spend a relaxed morning riding the free island trolley, wandering through festive sights or enjoying a leisurely meal at nearby restaurants. Prefer to stay...
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Conveniently located 3 miles to the pristine beaches of Anna Maria Island. Spoonbill Lagoon features 2- bedrooms plus a den and 2 full and one-half bathrooms with easy access to Anna Maria Island, the Bradenton and Sarasota areas, and Tampa Bay. This well-appointed home features a king master ensuite...
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Unwind at the Tropical Jewel Escape nestled among swaying palm trees and lush greenery. Close to IMG, Robinson Preserve, stunning beaches on Anna Maria, top restaurants, shopping and more. Tucked in a quiet, peaceful neighborhood, perfect to escape and recharge. Inside you’ll find spacious rooms...
Featured review
Needs some help with pool upkeep, Also needs vacuum to help with upkeep of pool area! We also needed swifter mop to keep kitchen and dining area clean! Carpet needs cleaned! Location and area was very...
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Celebrate spring at The Grove, where Florida sunshine, gentle breezes, and the vibrant energy of the season replace gray winter days. Trade coats for flip-flops and wander palm-lined streets, savoring warm mornings and sun-drenched afternoons. Location is key @ , relax on nearby sandy beaches, or enjoy...
Distance to beach: 12 miles to Manatee Public Beach
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Our you ready to plan your vacation, a time to enjoy the sea, sun and sand. Our large spacious open plan villa provides a haven where you can enjoy your vacation. The villa overlooks a tranquil lake which attracts an abundance of Florida wildlife. Our home is fully equipped for that home from home...
Featured review
Nous avons passé 8 jours dans la maison et elle était vraiment parfaite. La cuisine est très grande et super bien équipée. La climatisation efficace et silencieuse. Tous les lits étaient confortables....
Distance to beach: 12 miles to Holmes Beach
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This luxurious 3 bed / 2 bath home is situated on a larger than usual plot. The villa has full air conditioning / heating, is very spacious and airy and features many upgrades. There is a large central lounge / dining area and fully fitted open kitchen with breakfast area, den, laundry room (washer...
Featured review
Great location, clean, excellent communication. Enjoyed our extended stay, felt like home. Thank you for allowing us to stay in your home.
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Winter at The Betts offers the best of it all-luxurious finishes, a heated swim spa, fire pit, patio with outdoor dining, and a full front porch perfect for hours of family fun. Just steps from the downtown Riverwalk, enjoy boutique shopping, waterfront dining, the Farmer’s Market, and the Downtown...
Featured review
What a beautiful house. I wish I lived there. ( : Great location, great amenities and close to everything!
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The perfect family vacation destination THE SPACE Discover the charm of this beautifully renovated 5-bed, 2.5-bath, 2400 sq ft home with a welcoming open layout. Relax by the heated pool among family fun amenities, there's something for everyone! Located near a public boat launch for fishing...
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Spend your days playing in the pool and soaking up the sun at this coastal escape! The huge screened lanai includes a pristine new heated saltwater pool with a spillover spa and sun ledge, outdoor living and dining space, pool toys and lawn games. The updated 3 bedroom, 2 bath interior is bright and spacious,...
Featured review
The pool and hot tub was definitely the highlight of this place. The second place award goes to the large wifi/TV that allowed us to view some family videos from our laptop onto the big screen, as well...
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Whether you are looking for a family-friendly vacation, winter getaway, IMG Academy visit, romantic retreat or you just want to relax and enjoy the Florida sun on the award-winning Gulf Coast beaches, then this condo might just be the right fit for you. This luxurious, beautifully renovated and fully-equipped...
Featured review
We enjoyed our stay in this apartment. It is a big, bright apartment fully equipped and freshly renovated. Conveniently located just 5 minute's drive to IMG Academy and 10 minutes to the beaches, a short...
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Escape the cold and enjoy sunny Florida at this beautifully remodeled 3-bedroom, family-friendly bungalow with a private heated saltwater pool in Bradenton. Designed for comfort, fun, and relaxation, this home is perfect for families, snowbirds, and winter vacationers looking for a warm-weather getaway. Start...
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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...
Featured review
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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SUPERHOSTVERIFIED FOR CLEANLINESS + COMMUNICATION Spacious Bradenton Oasis Near IMG Academy & Beaches! Welcome to your ultimate vacation retreat in beautiful Bradenton, FL! Just minutes from world-renowned IMG Academy and a short drive to: Coquina Beach (5mi), Cortez Beach (6mi), Manatee Public...
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Luxurious Waterfront Living with Resort-Style Amenities: 2 Bed, 2 Bath Condo 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 enjoy the manatees or catch dinner!...
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Welcome to Palma Rosa! Embrace the tropical lifestyle in this clean and updated home with a private screened & heated pool and covered dining/lounge area with a 58" outdoor TV! The interior of the home is bright and spacious with cheerful coastal decor, and nearly every room flows directly to...
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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...
Distance to beach: 10 miles to north lido beach
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**boat rental available, please inquire for prices** This gorgeous oasis creates the perfect Florida vacation! The private dock leads to the crystal blue waters of the Sarasota Bay that is filled with dolphins, manatees, and gorgeous sandbars. You truly feel like you are in paradise in this amazing backyard...
Featured review
This is the second time we rented "The Yellow House". Convenient to multiple vacation areas Great biking options, close to two Crunch gyms, Anna Maria Island, shopping choices,
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The Shorewalk Complex is located along Cortez Avenue, the 'main-drag' in Bradenton. Sarasota Bradenton Airport is 15 miles from Shorewalk and Tampa International Airport is about 50 miles away. Ellenton Prime Outlet Mall is a 20 minute drive up I-75 N. Thrill seekers can enjoy Busch Gardens...
Featured review
The condo is downtown Bradenton. Easy access to groceries by walk, close to beaches. The area is sécure, clean and have shuffle bord, pool.
Distance to beach: 4 miles to Anna Maria Island
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Luxurious Bay View Living with Resort-Style Amenities: 2 Bed, 2 Bath Condo in West Bradenton and the coveted Palma Sola Bay Club on the east side of Palma Sola Bay! Experience breathtaking panoramic bay views with amazing sunsets from the privacy of your own unit and walk the grounds to live, swim, or...
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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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Cheerful Serenity – Luxury Waterfront Oasis on Perico Bayou with Pool, Dock & Sunset Views Welcome 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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Welcome to "Casa Spoonbill"—a stylish 3-bedroom, 2-bath waterfront retreat featuring a private pool (heated during winter months), canal-front dock, and direct Gulf access. Just 2 miles from the sugar-sand beaches of Anna Maria Island and minutes from kayaking the scenic waterways of Robinson...
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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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Ready to unwind and relax? Welcome to “Sunshine Villa” a hidden gem just 2 miles from the beaches on Anna Maria Island. This property is located within Flamingo Cay, a quiet peninsula community of 150 homes. This boating "Key West" style community is located within biking distance...
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