Bradenton Vacation Rentals Cottages, condos, and single family homes for rent in and around Bradenton & Anna Maria Island Where Florida Anna Maria Island Bradenton Beach Holmes Beach Town of Anna Maria Bradenton Cortez Flamingo Cay IMG Palma Sola W. Bradenton - People 1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + 9 + 10 + 11 + 12 + 13 + 14 + 15 + 16 + 17 + Search View all Anna Maria & Bradenton Area Properties USA > Florida > Bradenton Visit Bradenton Nestled on the Manatee River and host of seven MLB teams’ spring training right in town or within a 30-90-minute drive, Bradenton is known as “The Friendly City.” Why? The city charmingly invites you in with its cultural offerings, including local art, over a dozen parks, and historical sites and museums that tell the story of Manatee County. Experience a laid-back pace when you vacation in Bradenton. Your Bradenton Vacation, Your Way.PoolsGood for GroupsPet Friendly Find Your Bradenton Rental The Sandy Trio - Dune Our Thing Holmes Beach, FL 2 Bdrms 2 Baths 6 Guests 5.0 View Details New PropertyFeatured Property Sea Star Bradenton, FL 3 Bdrms 2 Baths 8 Guests Pet Friendly View Details Crazy Mermaid Anna Maria, FL 4 Bdrms 2 Baths 8 Guests 4.8 View Details The Sandy Trio - Castaway Cove Holmes Beach, FL 2 Bdrms 1 Baths 5 Guests View Details Featured Property The Sandy Trio - A Wave From It All Holmes Beach, FL 3 Bdrms 2 Baths 6 Guests 5.0 View Details Popeye's Poole Paradise Bradenton, FL 2 Bdrms 2 Baths 6 Guests 4.7 View Details Royal Poinciana Bradenton, FL 2 Bdrms 2 Baths 7 Guests Pet Friendly 4.9 View Details Catalina Comfort Bradenton, FL 3 Bdrms 2 Baths 8 Guests 4.8 View Details Coastal Fairways Bradenton, FL 3 Bdrms 2 Baths 12 Guests Pet Friendly 4.7 View Details New PropertyFeatured Property The Crane's Nest Holmes Beach, FL 3 Bdrms 3 Baths 8 Guests Pet Friendly View Details Featured Property 11 Palms Bradenton, FL 4 Bdrms 5 Baths 12 Guests Pet Friendly 5.0 View Details New PropertyFeatured Property Hey Sunshine Bradenton, FL 4 Bdrms 3 Baths 8 Guests Pet Friendly View Details Island Time Bradenton Beach, FL 3 Bdrms 2 Baths 8 Guests View Details Sunset Oasis Bradenton, FL 3 Bdrms 2 Baths 8 Guests 4.9 View Details Casa Palmera Bradenton, FL 3 Bdrms 2 Baths 8 Guests Pet Friendly 5.0 View Details Sun Kissed Villa Bradenton Beach, FL 3 Bdrms 2 Baths 9 Guests 5.0 View Details Featured Property Blue Martini Holmes Beach, FL 3 Bdrms 3 Baths 6 Guests 4.7 View Details Coconut Paradise Bradenton Beach, FL 1 Bdrm 1 Baths 4 Guests 4.8 View Details New PropertyFeatured Property Sunshine Siesta Holmes Beach, FL 2 Bdrms 1 Baths 5 Guests View Details #3 on Avenue Sea Bradenton Beach, FL 1 Bdrm 1 Baths 4 Guests 4.8 View Details Featured Property Sea La Vie Bradenton Beach, FL 2 Bdrms 2 Baths 4 Guests Pet Friendly 5.0 View Details Sunshine Retreat Bradenton, FL 4 Bdrms 2 Baths 10 Guests Pet Friendly 4.5 View Details New Property Sunshine Rays Bradenton, FL 3 Bdrms 2 Baths 9 Guests Pet Friendly View Details Hunter’s Haven Cortez, FL 3 Bdrms 2 Baths 8 Guests View Details New PropertyFeatured Property Pink Pearl Holmes Beach, FL 4 Bdrms 3 Baths 8 Guests 5.0 View Details Coastal Escape Bradenton, FL 4 Bdrms 2 Baths 8 Guests Pet Friendly View Details Search while moving Featured Bradenton Vacation Rentals The Crane's Nest Holmes Beach, FL 8 Guests 3 Bdrms 3 Baths Sea La Vie Bradenton Beach, FL 4 Guests 2 Bdrms 2 Baths Hey Sunshine Bradenton, FL 8 Guests 4 Bdrms 3 Baths Blue Martini Holmes Beach, FL 6 Guests 3 Bdrms 3 Baths Pink Pearl Holmes Beach, FL 8 Guests 4 Bdrms 3 Baths Sunshine Siesta Holmes Beach, FL 5 Guests 2 Bdrms 1 Baths The Sandy Trio - A Wave From It All Holmes Beach, FL 6 Guests 3 Bdrms 2 Baths Sea Star Bradenton, FL 8 Guests 3 Bdrms 2 Baths 11 Palms Bradenton, FL 12 Guests 4 Bdrms 5 Baths Your Local TeamLocally Owned and Operated In BradentonWhen you rent with SkyRun, expect unparalleled, prompt, and personalized service that sets us apart from traditional rental corporations. Personalized Attention: Enjoy a direct relationship with your property manager, who is always available to address your questions and concerns promptly. Local Insights: Have questions about nearby activities or services? Our local team will provide recommendations to enhance your stay. Proximity & Support: We live, work, and play here in Bradenton. We are located near your property, ensuring rapid response and hands-on support whenever needed. Matt Cooper and his wife Alexa are the Owners of SkyRun Bradenton. As a former pro-basketball player in European leagues, Matt’s love of travel and adventure was a natural catalyst for the Cooper family to enter into the vacation rental business. Matt, Alexa, and their daughter reside locally full-time. Matt & Alexa CooperBradenton, FL941-241-3055Email Matt Property Management You Can Trust Owning a vacation rental should be rewarding and enjoyable. Let SkyRun ease your worries and increase your revenue with our vacation rental management. Why choose SkyRun? As a local business with franchise-level tools, we offer personalized care and advanced technology. We handle marketing, maintenance, and guest services, ensuring a stress-free experience. Our homeowners are not just a number to us, they’re our neighbors! Get in Touch The entire process has been incredibly smooth, providing us with a true sense of peace of mind. From property management to timely payments, it’s been hassle-free. We couldn’t be happier with the service provided by SkyRun. Melissa TaylorW. Bradenton, FL Matt was very clear from the start and helped us build real expectations for our investment property. We’re pleased with how easy the process has been. Paul & ClaireBradenton, FL Matt gave a realistic number and also hit that number. My properties have been renting solid. He’s been so good that I continue to buy houses to have him run. NathanBradenton, FL Beaches Things to Do Deals What To Expect Check-In Instructions Property Damage Waiver Travel Insurance Bean PointAt the island’s most northern point, you’ll find the community of Anna Maria. Bean Point Beach is Anna Maria’s most peaceful beach locale, known for its stunning sunsets and picturesque views of Tampa Bay and the state park and national wildlife refuge, Egmont Key. You can also enjoy Bayfront Park, which is just around the corner (and walkable) from Bean Point Beach on the island’s bayside. Holmes BeachHolmes Beach sits in the center of Anna Maria Island and offers three miles of sandy beaches. The most popular option is Manatee Public Beach, which provides plenty of room for relaxation, playing volleyball, or walking along the shoreline. Manatee Public Beach also has picnic tables and grills, and restrooms and showers, ideal for a family get-together or a full beach day. Bradenton BeachBradenton Beach is the southern community of Anna Maria Island, and is home to the lovely Coquina Beach and Cortez Beach. Perfect for swimming, Coquina Beach sits at the lower edge of the island, right before Longboat Pass Bridge. A little further up you’ll find Cortez Beach, which offers a quiet, family-oriented environment. Every beach offers awe-inspiring views of the sunset. Manatee RiverNo shock here–the Manatee River provides opportunities to watch manatees as they feast on river fare and swim in their natural habitat. Boat tours take you to manatee hot spots or maybe grab the kayak or canoe and share the waters. Bass, catfish, and bluegill share these waters, so pack your poles and rods. Keep your activities on land when you explore the river’s DeSoto Memorial Trail. Anna Maria IslandDiscover Anna Maria Island’s history, wildlife, and South Florida delights. The Anna Maria Island Historical Museum offers a glimpse of Florida’s history, and check out the Anna Maria City Jail at Pine Avenue, which dates back to 1927. The island is also known for the large population of bottlenose dolphins that frequent its waters. You can also take a walk along the Coquina Baywalk, a one-mile stretch where you can get a close-up view of Florida’s native plants and animals. Bradenton RiverwalkThe heart of Bradenton! Stroll the more than one mile stretch and get to know Brandeton. Saturdays from October to May, wander through the Bradenton Market and delight in fresh Florida produce and hand-crafted goods. Summer visitors can enjoy the Summer Mini-Market on second Saturday mornings from June until August. Check out concerts, seasonal events, or just enjoy strolling along the river. Savor South Florida cuisine (and yes, the abundant seafood) at one of the area’s eateries. History, Science, and CultureExplore Florida’s ecosystems at the Bishop Museum of Science and Nature where science fans can see conservation at the Parker Manatee Rehabilitation habitat. Check out rotating exhibitions as well as the planetarium to take you to the stars. Come back down to Earth and roll back time with a visit to the Manatee Village Historical Park. Just off of Old Main Street, this immersive historical experience ensconces you in Old Florida. Restored buildings dating back from 1860 include a court, schoolhouse, general store, and even a blacksmith forge. Wander through the village and imagine life more than a century ago. WatersportsWater sports are the name of the game Bradenton. Nearby Holmes Beach, Bradenton Beach, and Anna Maria Island play host to crystal clear waters perfect for swimming, playing, or just relaxing. Grab a kayak and check out the mangrove trees that grow directly out of the water. The calm seas are also a perfect place for paddleboarding. If you don’t have your own equipment, you can purchase or rent from a number of local businesses. FishingWhether you’re an avid fisherman or a first-timer, you’re guaranteed to have a great day on the water. Fishing along the Manatee River gives ample chances for scoring bass, bluegill, and catfish hauls. Head to the ocean and check out the Rod and Reel Pier, the City Pier, or the Bradenton Beach Pier. All three places allow you to rent rods and purchase bait at low prices. For a more guided experience, you can also book a chartered fishing trip on a boat with all equipment included in the cost. Play Ball!South Florida offers baseball teams and fans a respite from winter’s grip when teams set up camp for Spring Training. The Pittsburgh Pirates set up their Florida can Bradenton’s LECOM Park. If you’re in town during Spring Training, check out the Pirates battle other MLB teams. Fun fact–LECOM Park is the country’s oldest continuously operating spring training facility. ShoppingGet a taste of Bradenton’s past when you shop, sip, and stroll your way through Bradenton’s Old Main Street. Art galleries, boutiques, and restaurants line this stunning stretch–a feast for all the senses. COMPASS BOAT RENTAL Compass Boat Rentals is one of the best companies to rent boats at, plus get 10% off for being a SkyRun guest. Book here BAYSHORE FISHING CHARTERS SkyRun Homeowners and Guests receive 10% off of all services with this local charter company. Book here AVIS & BUDGET CAR RENTALS Receive preferred pricing on car rentals with Avis or Budget. Car pickups available in airports our guests often use or at any other Avis/Budget location. Avis is a leading rental car supplier positioned to serve the premium commercial and leisure segments of the travel industry, and Budget is a leading rental vehicle supplier focused primarily on more value-conscious segments of the industry. Avis Budget Group is dedicated to being a best-in-class Customer Led, Service Driven organization. Book here THE CHEESECAKE CUTIE The Cheesecake Cutie & Cafe is the perfect spot for a sweet dessert. SkyRun guest save 10% off! Learn more FREEDOM JET SKI RENTALS Experience the euphoric freedom of being on the waves with FREEDOM JET SKIs, where they provide safe & fun Jet Ski Watersport Services with additional supplemental options to enhance the thrill of your Waverunner adventure! SkyRun guest save 10% off! Book here CAROUSEL SEA HORSES Check out Florida’s most popluar horseback riding excursion! Anna Maria guest get the “Picture Package” included for FREE. Book here FUTURE SKYRUN STAY We are always receiving happy guest reviews about SkyRun services and employees, experiences, and properties. Furthermore, guests express their desire to come back and stay with us again which is why we’d like to offer you the chance to do so. Plus, we get to see your lovely faces again! Book another SkyRun stay while you are here and get 10% off! Free Island TrolleyThe Anna Maria Island Trolley makes it easy to get around the island. The free trolleys loop the island from north to south and can even accommodate bikes. Hop on and off as much as you like! See routes and times here. What To Expect Get that “home away from home” feel while enjoying the streamlined, convenient guest experience that includes full attention to every detail. During your stay, you can expect SkyRun staff to be close by and available to help you make the most of your trip. You can reach them via web chat, email, text, or phone. They’re available and accessible daily, and on-call 24/7 for emergencies. What’s included Independent homeowners contract with SkyRun Vacation Rentals to professionally manage their properties and create stellar vacation experiences for their guests. Every SkyRun property is unique, so certain features and amenities are variable. To ensure you’re selecting the right property for your needs, review the photos and note the amenities listed for the property. Read the sections called “What you’ll love” and “What to be aware of” at the bottom of each listing, and check out reviews from prior guests. Included Services: Full cleaning prior to your arrival Pre-arrival inspection Wi-Fi and TVs Most properties have free parking (check each property for possible charges) Luxury linens and towels Fully stocked kitchen Cleaning and trash removal upon departure Included Amenities and Starter Supplies: Coffee and coffee filters (if applicable) Salt and pepper Soap/shampoo/lotion Toilet paper Paper towels Hair dryer Ironing board Dish soap and dishwasher detergent (if applicable) Laundry detergent (if applicable) Alarm clock Firewood (if applicable) Additional Services: Crib or toddler bed with sheet: $10/day Pump-up bed with sheets: $10/day Mid-stay cleaning service: Ask your local SkyRun staff for pricing Grocery delivery: call for pricing Travel insurance: 7% – 9.5% of your trip cost Check-In Instructions Check-In: Check-in is 4:00 p.m. ET Seven days prior to the arrival date, guests will receive an email that contains directions and access information for the property. In most cases, guests will access a property via a lockbox or smart lock using an access code. Early check-ins can be confirmed only on the day of arrival. Check-Out: Check-out is 10:00 a.m. ET. Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with the SkyRun office. Late check-outs must be coordinated directly with the SkyRun office no later than 9 a.m. on the day of departure. Please note that if we have an incoming guest we will not be able to accommodate a late checkout. We ask that guests remove major trash from the unit, return the furniture to its original location, and load and run the dishwasher. Parking: Parking may be limited. The check-in instructions email will contain information regarding parking at your property. Any parking fines assessed to your vehicles during your stay will be billed to you if they are billed to us. Parking fines can be significant. Property Damage Waiver Enjoy peace-of-mind with our incidental damage protection. SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure. It does not cover damage that is willful, the result of negligence, or damaged caused by the misuse of household items. It also doesn’t cover unreported damage. SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is nonrefundable. If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is provided to you and all travelling companions that are staying in the home overnight during your stay. Coverage is not provided for loss due to: Your intentional acts or gross negligence. Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party). Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you. Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report. Your Duties in the Event of Damage. You must: Take all reasonable, necessary steps to protect the property and prevent further damage to it. Report the loss in writing (email ok) prior to check-out to the SkyRun staff. Provide us documentation such as pictures to substantiate the claim. Travel Insurance Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more. Group coverage protects everyone in your traveling party for one low price. Get a quote. Bradenton Blog Top Gulf Coast Destinations Read More Maximize Your Vacation Home’s Potential with Expert Property Management in Anna Maria Island, Bradenton & Holmes Beach Read More SkyRun Named Among Top New & Emerging Franchises Read More Short-Term vs. Long-Term Rentals Read More View All Explore Nearby Areas Anna MariaSarasotaSiesta Key Bradenton Frequently Asked Questions How do I know I’m getting a good vacation rental? SkyRun provides photos, maps, amenity details and reviews about the property you will be renting. Our staff has first-hand knowledge of each property, so don't hesitate to call us if you have any questions. What’s included with my rental? We provide everything you expect from a fine hotel, and then some. Our rentals come fully furnished, including TVs, high-speed internet, linens and towels, a microwave, dishes, pots, pans, and other kitchen essentials. We provide supplies such as shampoo, conditioner, tissues, paper towels, dishwasher detergent, soaps, trash bags, etc. Refer to individual listings to see more amenity information, and please contact us directly if you still have questions. Am I getting a good deal? When you book directly with SkyRun you avoid paying service fees you might incur with traditional listing channels, such as Airbnb. Our prices are competitive with rent-from-owner rates, but we offer professional service, optional travel insurance, and immediate on-site assistance should the need arise. In addition, we offer exclusive discounts from local businesses, available only to SkyRun guests. How does travel insurance work? Travel insurance is an optional addition to your total rental charges. It is offered on our reservation form at the time of booking. It is also usually offered at the time of booking when you book with a 3rd party booking site. You may also add travel insurance to your reservation within 48 hours of booking. The cost of travel insurance varies and is usually between 7%-9.5% of your total reservation cost, depending on the coverage type. If you do not have travel insurance, you cannot cancel your reservation for any reason. If you have travel insurance and need to cancel or make a claim, refer to your specific policy. How do I rent a property? What are the deposit and payment terms? You can rent any of our properties by booking directly on this website using a credit card or you can call to book a reservation if you would like to speak with a vacation planner. When you book, 1/3 of your total reservation cost, or a minimum of $300, is charged as a non-refundable deposit to secure your rental. Thirty days before your arrival, the remaining amount is due. At this time, the credit card we have on file will be automatically charged for the balance. You may cancel for a full, no-questions-asked refund up to 14 days before your arrival. After that, your payment becomes non-refundable. (See travel insurance above for exceptions). How do I check-in? For most properties, SkyRun utilizes a convenient keypad lock system which allows you to enter your vacation rental using a personalized access code, as opposed to having to pick up a key and worrying about keeping track of it during your stay and returning it afterwards. This also saves you the trouble of coming to a check-in center beforehand. Your welcome packet will be in your rental upon arrival, and our staff is always only a phone call away if questions arise. What are the house rules? Remember you are staying as a guest in someone's home, where much investment has been made to make your stay enjoyable; please treat all private property with the respect it deserves. No smoking and no pets (unless specifically designated as pet-friendly). No parties that exceed the number of people the property sleeps are allowed in the rental at any time. Renters are subject to citations for noise violations, etc., handed down by public officials. Is there a property-damage protection waiver? SkyRun includes a property damage protection waiver on each reservation. Coverage is provided to you and all traveling companions who are staying in the home overnight during your stay. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure. It does not cover damage that is willful, the result of negligence, or damage resulting from the misuse of household items. It does not cover unreported damage. SkyRun doesn't charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is nonrefundable. If, during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss,” and the property owner's insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is not provided for loss due to: Your intentional acts or gross negligence. Any damage that occurs if you are in violation of the terms and conditions of your rental agreement (including, but not limited to, having more than maximum occupancy or having a party). Loss, theft, or damage to any personal effects owned by you or brought on the covered stay by you. Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation, unless substantiated by a police report. In the event of property damage, you must: Take all reasonable, necessary steps to protect the property and prevent further damage to it. Report the loss in writing (email is OK) prior to check-out to the SkyRun staff. Provide us with documentation, such as pictures, to substantiate the claim. Sign up for emails Trip inspiration, special offers, and vacation planning tips. 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