Anna Maria Island Vacation Rentals

Cottages, condos, and single family homes for rent in and around Anna Maria Island & Bradenton

View all Anna Maria & Bradenton Area Properties

USA > Florida > Anna Maria Island

Visit Anna Maria Island

Located on the stunning Gulf Coast of Florida, Anna Maria Island is a tropical paradise that lures tourists with its white sandy beaches, turquoise waters, and laid-back atmosphere. This charming barrier island offers a peaceful retreat with quaint beachside towns, delicious dining options, water sports activities, and breathtaking sunsets, making it an ideal destination for relaxation and rejuvenation.

Your Anna Maria Island Vacation, Your Way.

Find Your Anna Maria Area Rental

Bradenton, FL

3 Bdrms 2 Baths 6 Guests
From $142.00
per night + taxes & fees

Holmes Beach, FL

2 Bdrms 2 Baths 4 Guests
Pet Friendly
From $110.00
per night + taxes & fees
New Property
Featured Property

Holmes Beach, FL

3 Bdrms 3 Baths 8 Guests
Pet Friendly
From $189.00
per night + taxes & fees

Bradenton, FL

2 Bdrms 2 Baths 6 Guests
From $151.00
per night + taxes & fees

Holmes Beach, FL

2 Bdrms 2 Baths 4 Guests
Pet Friendly
From $131.00
per night + taxes & fees

Holmes Beach, FL

2 Bdrms 1 Baths 6 Guests
From $121.00
per night + taxes & fees

Bradenton, FL

3 Bdrms 2 Baths 8 Guests
From $219.00
per night + taxes & fees

Bradenton Beach, FL

2 Bdrms 2 Baths 4 Guests
Pet Friendly
From $123.00
per night + taxes & fees

Bradenton Beach, FL

3 Bdrms 2 Baths 9 Guests
From $185.00
per night + taxes & fees
Featured Property

Holmes Beach, FL

3 Bdrms 3 Baths 6 Guests
From $235.00
per night + taxes & fees

Holmes Beach, FL

2 Bdrms 2 Baths 6 Guests
From $176.00
per night + taxes & fees

Bradenton, FL

4 Bdrms 2 Baths 10 Guests
Pet Friendly
From $189.00
per night + taxes & fees

Bradenton, FL

3 Bdrms 2 Baths 8 Guests
From $163.00
per night + taxes & fees

Bradenton, FL

2 Bdrms 2 Baths 7 Guests
Pet Friendly
From $142.00
per night + taxes & fees

Bradenton Beach, FL

1 Bdrm 1 Baths 4 Guests
From $110.00
per night + taxes & fees

Bradenton, FL

3 Bdrms 2 Baths 12 Guests
From $154.00
per night + taxes & fees
Featured Property

Bradenton, FL

4 Bdrms 5 Baths 12 Guests
Pet Friendly
From $331.00
per night + taxes & fees

Bradenton, FL

3 Bdrms 2 Baths 8 Guests
Pet Friendly
From $227.00
per night + taxes & fees
Featured Property

Holmes Beach, FL

3 Bdrms 2 Baths 8 Guests
From $223.00
per night + taxes & fees

Bradenton, FL

3 Bdrms 2 Baths 12 Guests
Pet Friendly
From $180.00
per night + taxes & fees

Bradenton, FL

4 Bdrms 2 Baths 8 Guests
Pet Friendly
From $176.00
per night + taxes & fees

Bradenton Beach, FL

1 Bdrm 1 Baths 4 Guests
From $106.00
per night + taxes & fees

Anna Maria, FL

4 Bdrms 2 Baths 8 Guests
From $189.00
per night + taxes & fees

Holmes Beach, FL

2 Bdrms 1 Baths 5 Guests
From $118.00
per night + taxes & fees
New Property

Bradenton, FL

3 Bdrms 2 Baths 9 Guests
Pet Friendly
From $176.00
per night + taxes & fees

Featured Anna Maria Island
Vacation Rentals

Your Local Team

Locally Owned and Operated In Anna Maria Island

When 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 Anna Maria Island. 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 Anna Maria Island. 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 full-time on Anna Maria Island.

 

Matt & Alexa Cooper

Anna Maria Island, FL

941-241-3055

Email 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

Bean Point

At 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 Beach

Holmes 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 Beach

Bradenton 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.

Watersports

Water sports are the name of the game on Anna Maria Island. Enjoy a swim in the crystal clear ocean or grab a kayak and check out the mangrove trees that grow directly out of the water. The calm waters 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.

Fishing

Whether you’re an avid fisherman or a first-timer, you’re guaranteed to have a great day on the water. For land-based fishing, 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.

Wildlife Watching

One of the most beautiful parts of Anna Maria Island is the abundance of wildlife on and around the island. The island is 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.

Biking

Immerse yourself in the small town lifestyle of Anna Maria Island by getting into the local cycling culture. Biking is not just a great way to enjoy the scenery, it’s also a popular form of transportation, since parking on the island is limited. If you don’t have your own bikes or don’t want to bring them with you, you can easily arrange for daily or weekly rentals.

Dining

It probably comes as no surprise that seafood appears on most menus across the island. A popular place is the Anna Maria Oyster Bar, where you can enjoy the day’s catch while relaxing with a waterfront view. In addition to seafood, there are plenty of other options ranging from fine dining to casual. Many restaurants offer indoor and outdoor seating options. 

History and Culture

Anna Maria Island has a very rich history just waiting to be discovered! Check out the Anna Maria Island Historical Museum, run by the Island Historical Society, where you can get a glimpse of Florida’s history and learn about the rich history of the island. You’ll find several historical landmarks at Pine Avenue, including the Anna Maria City Jail. It was built in 1927 and is one of the most photographed places on the island.

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.

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.

THE CHEESECAKE CUTIE

The Cheesecake Cutie & Cafe is the perfect spot for a sweet dessert. SkyRun guest save 10% off!

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!

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!

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.

Explore Nearby Areas

Anna Maria Island Frequently Asked Questions

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.

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).

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.

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.

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.

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.

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.

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.

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