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Are you looking for a sunny escape? Our monthly rentals in Bradenton, Florida, offer the perfect opportunity to unwind and enjoy everything this charming coastal city has to offer. Whether you're looking for a winter retreat or a long-term stay, Bradenton is full of natural beauty, cultural attractions, and outdoor adventures.
Distance to beach: 10 miles to Anna Maria Island Beach – 10 minutes away
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The Grand Gathering House – 11BR Retreat Perfect for Bridal Parties & Big Groups! Welcome to your ultimate group retreat in sunny Bradenton, Florida! This one-of-a-kind property features 12 bedrooms and 6 bathrooms, comfortably accommodating up to 24 guests, making it ideal for bridal parties,...
Distance to beach: 15 miles to Seiasta Key Beach
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The luxurious Club and amenities will be bringing you and your family an unforgettable time!! Unlimited golfing for around 50% less fee , and 9 Har-thru tennis courts, pickle ball courts; a state of the art fitness center; spa; zero entry lagoon swimming pool and hot tub with handicap access; Tiki bar,...
Featured review
The location of this unit in Lorraine Lakes is within walking distance to the pool and clubhouse, which is great. Dani was very responsive to any questions while we were there. The home's layout is perfect...
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...
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Very comfortable on the inside with enough beds and room for 6 people. Fully furnished on the inside with the design of a typical beach home. A backyard complete with outdoor dining area and bar island that are great for outdoor grilling. A big, fenced in backyard that is great for pets to run around....
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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Thank you to our guests for awarding us "Premier Partners" and "Super Hosts".Looking for a quiet, oasis just minutes to Anna Maria Island? Look no further.... Wake up to the birds chirping in the nature preserve directly in front of your screened terrace. Enjoy the pond view while...
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AVAILABLE – Short-Term Monthly Rental! Fully furnished home in Lakewood National Golf Club at Lakewood Ranch. 2,250+ sq. ft. with 3BR, den, and 2 baths.Spacious primary suite with private lanai, walk-in closet, and luxury bath. Open living areas lead to a covered lanai with preserve views and...
Distance to beach: 30 miles to Lido Beach
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Welcome to your resort-style escape in the prestigious Lakewood National Golf Club. This beautifully furnished two-bedroom, two-bathroom condo, located on the second floor, offers the perfect blend of comfort, luxury, and breathtaking golf course views.Step onto the private lanai and take in the peaceful...
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Beautiful 2 bedroom, 2 bath condo at Hidden Lakes with views of the lake and fountain. You can sit on the lanai and listen to the sound of water or take a short walk to the heated pool, hot tub, gym, library, or steam room. Our condo is decorated to give you the feel of staying on the beach, but you are...
Featured review
A Very spacious unit with a well equipped kitchen. The condo location is close to Downtown Sarasota events and activities. A perfect laid back condo atmosphere where you can fish in the Bayou or just...
Distance to beach: 5 miles to Anna Maria Island
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A recent review (December 2025 stay):"Rented this sight unseen and were very happy with the condo. Very central location, convenient amenities, clean with very nice people for neighbors. We are waiting for the paper work to rent it next December."Fully renovated, fully furnished 2BR/2BA...
Featured review
Very central location, convenient amenities, clean with very nice people for neighbors. We are waiting for the paper work to rent it next December.
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.
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...
Distance to beach: 26 miles to Siesta Key
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The condominium is in prestigious Lakewood National Golf Club and is fully furnished with a washer/dryer built in the unit for your convenience. 24/7 guarded Gated community with multiple pools within the community, tiki bar at the main pool. The condominium is on hole #10 of the Piper golf course and...
Featured review
Ashoka’s condo was very a comfortable stay. Everything was very easy and the condo was well stocked with everything we needed from cooking to laundry. We would happily rent again if we return to Lakewood...
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Perfect for snowbirds. First floor, 2-bedroom lakeside condo at Hidden Lake of Manatee. It is a gated condo community which offers a clubhouse with ping pong table, lending library and small fitness center. The condo features 2 bedrooms each furnished with one 1 queen bed, dresser, and TV. Work desk...
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Completely updated golf front condo with club privileges. Top floor unit, great view and all the best country club features. Great golf course, multiple pools, tennis, pickle ball, bocce ball. Formal restaurant, casual bar and grill, poolside snack bar and lots of outdoor casual seating.
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SEP to DEC 2025 : $225 a day (Taxes and Fees Not Included) - MIN 30 DAY RENTALLUXURY ISLAND GATED COMMUNITY! Enjoy water views of Anna Maria Sounds and Harbour Isle private lake from this gorgeous 3+ Brdm / 3 Bath, 3,412 total sq. ft. high-end flagship coach home! The unit is fully furnished with...
Featured review
Couldn’t be a better location as the glorious beach was two minutes away! And what a fabulous beach to walk. The sunsets were spectacular. Couldn’t get any more beautiful.
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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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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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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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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.
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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: 5 miles to Manatee Public Beach
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Nestled in a peaceful neighborhood, this soothing house offers the perfect escape for guests seeking tranquility. Totally renovated 3 bedroom, 2 bath interior is bright and spacious. Quick access to Anna Maria Island beaches, IMG, walking trails, parks, shopping & restaurants! Bring the whole family...
Distance to beach: 17 miles to Siesta key
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Rarely available Penthouse, top floor, end unit! Live a stylish urban lifestyle in a friendly town. Enjoy a view of the downtown fountain, shops & restaurants. "The Lofts on Main" is located in the heart of Lakewood Ranch, voted #1 Multi-generational Community in the United States for 4...
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Welcome to Your Cozy Florida GetawayWelcome to our charming and peaceful home, perfectly located between Sarasota and Bradenton. This prime location allows you to enjoy the best of both beautiful coastal areas while staying in a quiet and friendly neighborhood.Our home offers a relaxing atmosphere...
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Rv fo rent in backyard across the street from Palma sola elementary school. It has 1 bedroom, 1 bathroom a full kitchen, dinette and deck. The closest beach is about 5 minutes drive and the main barrier island is about 10 minutes drive. fully furnished.
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Located in Beautiful Tara Golf and Country Club on lake. Our full private golf club membership can be transferred to you, allowing you to golf, and use all facilities, heated community pool with Spa, tennis courts, pickle ball, bocce, state of the art gym, and club house offering restaurant, bar and many...
Featured review
Excellent well appointed home with great decor and lots of space.Whilst an excellent property there are several issues which mean we would not rent this property again.1) the design of the pool...
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Bungalow at Margaritaville! Sunrise Views and Bird Watching from your Private Lanai Short drive to the World Class Beaches of Anna Maria Island Community Pool, Splash Pad, Playground, and Activity Area Walk to Floridays or take a stroll around Robinson Preserve Fully stocked kitchen for all...
Distance to beach: 30 miles to Siesta
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You’ll love this stunning 3rd Floor Condo, and what a view from the 3rd floor! it has 2 bedrooms with golf course & lake view at Lakewood National located in Lakewood Ranch.This one-of-a-kind Arnold Palmer designed 36 Holes Golf Course is a real champion nearly 900-acre enclave set within the...
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Welcome to Penthouse Retreat! 1 Mile to the World Class Beaches of Anna Maria Island Close proximity to Bradenton, Lakewood Ranch, Sarasota, and Tampa Community Pool, Splash Pad, Playground, and Activity Area Walk to Floridays or take a stroll around Robinson Preserve Fully stocked kitchen for...
Distance to beach: 24 miles to Anna Maria Island
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ESPLANADE AT LAKEWOOD RANCH! This beautiful turnkey home with magnificent views of the 12th fairway and serene views of a lake and the many birds and other wildlife from the covered and screened lanai is located on a quiet cul-de-sac. As you enter through the front door, the great room floor plan is open...
Featured review
We rented from Raj from January 24th through March 31st and everything exceeded our expectations. The house was immaculate and was well stocked with cooking equipment, dishes, glasses, storage containers,...
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Welcome to Castaway in Margaritaville! Short drive to the World Class Beaches of Anna Maria Island Close proximity to Lakewood Ranch, Sarasota, and Tampa Gated community with pool and amenities Walk to Floridays or take a stroll around Robinson Preserve Fully stocked kitchen...
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Welcome to 128 Sweet Tree! Close proximity to Lakewood Ranch, Sarasota, Tampa, and Gulf Coast Beaches Private Screened in Heated Pool/Spa Social Membership Available Fully stocked kitchen for all of your favorite home cooked meals Smart lock for Self Check-in Queen or larger beds and TVs in every...
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Bring the whole family to this great place with lots of room for fun. A spacious 2 bedroom, 2 bathroom newly renovated and fully equipped condo. Whether you are a single family on vacation, or a couple enjoying a gateway we have you covered. Stay with us and enjoy all the comforts of home!This delightful...
Featured review
Thank you Maja and family for use of your Bradenton villa for my Winter retreat this year. I enjoyed the villa and area so much, I extended through April. So many great things to do and visit in the area....
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Welcome to Holmes Beach Retreat! Sleeps 7 Water Views of Anna Maria Sound! Sunset Views and Bird Watching from your Private Lanai Short drive to the World Class Beaches of Anna Maria Island Walk to Floridays or take a stroll around Robinson Preserve Fully stocked kitchen for all of your favorite home...
Distance to beach: 5 miles to Ana Maria Island
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Spacious two- bedroom condominium located in the newly developed community of Palma Sola Bay Club in West Bradenton. Entering this unit, you are greeted by the 30 acres nature preserve and Palma Sola Bay from the living room. You will enter the spacious Master Bedroom suite through over sized double...
Featured review
When we arrived for our rental, we were well pleased because it exceeded our expectations. The layout was unusual, but awesome. The condo was well kept, and the quality of the furniture quality met our...
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Spacious 3BR/2BA Private Pool Home – Family-Friendly, Fully Equipped & Minutes to Gulf BeachesEnjoy the best of Florida’s Gulf Coast in this charming, fully furnished vacation rental in Bradenton, FL, located just 13 minutes from Anna Maria Island’s world-famous beaches! Ideal...
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Luxury-furnished waterfront home — recently renovated top-to-bottom with true designer quality (West Elm level), not the typical “condo leftovers.” High ceilings, walls of glass, and a light-soaked great room looking straight out over the river, oaks and untouched preserve land —...
Featured review
The owner was wonderful to work with, the location couldn't be better! It was very relaxing to enjoy the back screened in porch overlooking the river, peaceful and secluded! Recommend!
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This 3 bedroom plus den home with 3.5 baths, garage, pool, spa, outdoor kitchen is a fully furnished luxury home overlooking a lake and the golf course. The house spans across 2800 sq ft with a very open plan and is located in the upscale Esplanade Golf and Country Club. The home is beautifully furnished...
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Located only one mile to the beautiful beaches of SMI. The White-sand Beaches of the Gulf of Mexico is a short 1 min drive away. An extra large heated pool is across the driveway away in a beautiful tropical setting with bathrooms and an outdoor shower to rinse off! There is also a hot tub to relax...
Featured review
The vacation was amazing. My family had so much fun. We needed this time to relax and get out to the water after being shut in for so long.
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Northwest bradenton, large fenced in backyard, 10 minutes from Anna Maria island. 37 feet. Everything included utilities, electric, internet.
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This is a duplex 2 Bedroom and 1 Bath space renovated, cozy and beautiful, Fully equipped so you can enjoy a pleasant and comfortable stay. Totally private and independent. Located in a very quiet and safe neighborhood, just 15 minutes from Anna Maria and other beautiful beaches, nature reserves and other...
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Welcome to Jerry's Gem! Close proximity to Lakewood Ranch, Sarasota, and Tampa Short drive to the world class beaches of Anna Maria Island Fully stocked kitchen for all of your favorite home cooked meals High speed Wi-Fi included, Smart lock for Self Check-inThis property is located in...
Distance to beach: 3 miles to Anna Maria/Bradenton Beach
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Welcome to a waterfront paradise. This resort style condo is a spacious 2 bedroom 2 bath condo that is is fully furnished with a completely stocked kitchen. Everything you will need away from home! New luxury vinyl flooring throughout, new A/C and hurricane impact windows all 2024. Ceiling fans throughout...
Distance to beach: 18 miles to Siesta Key Beach
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Luxury Coach Home on first floor for couples, families (with kids), and big groups . 3 Bedroom /Two Big Baths/Two Car Garage-- an endless vacation lifestyle akin to a resort style vacation Home! The luxurious Club and pools will be bringing you and your family an unforgettable time!! Coming with membership...
Featured review
Our family had the best stay here! I can’t say enough positive things. When we arrived, we were greeted at the gate and escorted around to tour all the amenities in the community. Everyone was so nice...
Distance to beach: 7 miles to Holmes Beach (Anna Maria)
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Turnkey fully furnished 2 bedroom 2 bath villa condo. This condo is located is located in the IMG/El Conquistador Country Club area just a block from IMG Academy. The condo is fully furnished and ready to go. The community features a heated pool and clubhouse. Located a short drive to the nearby beaches...
Distance to beach: 5 miles to Anna Maria Island
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55+ Senior Special - Burgundy One Condo Community= 2nd floor walk up - corner unit - light. bright and airy = parking at door - granite and all new cupboards and flooring - pool, shuffleboard, clubhouse & activities, laundry, queen bed, single bed conversion sofa, shopping & restaurants &...
Distance to beach: 10 miles to Anna Maria Island
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LOCATION: Beautifully remodeled 2BR/2BA first floor condo with front door parking! This tranquil, but active 55+ community is nestled comfortably between downtown Bradenton and the beautiful Gulf of Mexico beaches on Siesta Key and Anna Maria Island. Located close to shopping, dining, banking, golfing,...
Featured review
Close to everything you need: shopping, groceries, restaurants and beach. Pool out the back door was a convenience. Nicely decorated with comfortable beds.
Take a look at our selection of monthly rentals that cater to all preferences. Whether you're after a cozy condo close to the downtown area or a spacious home by the beaches, Bradenton offers a wide variety of rental options. Enjoy the comfort and convenience of an extended stay in this lovely city on Florida's Gulf Coast.
Don’t miss out on the chance to stay in one of Florida’s hidden gems. Explore our listings of monthly rentals in Bradenton and find the perfect spot for your extended stay. With a variety of options available, you’re sure to find a rental that suits your style and needs, making your time in Bradenton truly memorable.
Thinking about your next trip? Reserve your spot early for future stays to guarantee the best rental options. Whether you're planning a winter escape or a summer vacation, booking ahead ensures you have the ideal accommodations ready for your arrival.
Large Group Rentals
Planning a group getaway? Bradenton has spacious rental homes that are perfect for large families or groups of friends. These rentals offer multiple bedrooms, bathrooms, and large living spaces, making them ideal for reunions or vacations with extended family. Enjoy the convenience of private pools, large kitchens, and plenty of room for everyone to relax.
Family-Friendly Monthly Rentals
Bradenton is a great destination for families. Our family-friendly rentals are equipped with amenities like private pools and game rooms, ensuring plenty of entertainment for everyone. With easy access to beaches, parks, and family attractions, your family will have a blast during your stay.
Romantic Getaways for Couples
Looking for a romantic escape? Bradenton has cozy monthly rentals perfect for couples seeking some quality time together. Enjoy quiet, private spaces with beautiful views, access to scenic beaches, and nearby dining options for intimate evenings. Whether you’re celebrating an anniversary or simply want to get away, Bradenton has plenty of options for couples.
Winter Retreats for Snowbirds
Bradenton’s mild winter climate makes it an excellent choice for snowbirds looking to escape colder weather. With average winter temperatures in the 60s and 70s, Bradenton offers a warm and welcoming environment for those looking to spend the winter months in comfort.
Secure your winter retreat in Bradenton by booking one of our monthly rentals. Experience all the warmth and relaxation Bradenton has to offer, and make your winter getaway one to remember. Browse our listings today to find the perfect long-term rental.
Bradenton is known for its beautiful coastline and outdoor attractions. When you stay in one of our monthly rentals, you’ll be close to a variety of activities, including:
💰 Highest rates
February
🎉 Busiest month
March
🏠 Popular home types
Condo and House rental
🔥 Hottest months
July and August
❄️ Coldest months
January and December
☔ Rainiest months
June and August
🌺 Best months for flowers
April and May
🌴 Peak tourist season
December to April
🍂 Quietest months
September and October
🌊 Best beach months
April and May
🏌️ Best golfing months
November to April
🎨 Top cultural events
Bradenton Blues Festival (December), ArtWalk Bradenton (Monthly)
🍽️ Best dining months
January to March (Restaurant Weeks)
🦋 Nature activities peak
March to May (Bird watching and hiking)
🛶 Water sports season
June to September
🏖️ Best months for shelling
May and June
📅 Local festivals peak
January to April
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