Meet the radiant duo of real estate expertise and cheerful service: Shandra and Jeff Holbrook, the driving force behind Cheerful Rentals and The Cheerful Coast Group. With a passion for making real estate transactions a positive experience, they bring a wealth of knowledge and a cheerful presence to the table.

Shandra Holbrook's journey to real estate was paved with a background in education and a genuine love for homes. Hailing from a family deeply rooted in the moving business, she understands the importance of a comfortable and secure living space. Shandra's career in education taught her the value of communication, organization, and patience – skills she now brings to her real estate practice.

A proud graduate of Anderson University (IN) with a degree in Elementary Education, Shandra transitioned into real estate to serve her community in a new way. With numerous accolades under her belt, including top rookie sales agent in 2019 and top monthly sales in January '21, she's committed to ensuring a cheerful buying or selling experience for her clients.

Shandra, together with her husband and teammate, Jeff, calls Bradenton, Florida home. They're dedicated parents to Samantha and John and are often found at Furman Football games and Georgia Southern Track meets. Whether you're working with Shandra or Jeff, you're working with both!

Jeff Holbrook boasts over 27 years of success in education as a teacher, coach, and school administrator. His genuine passion for helping others in and out of the classroom has earned him a place in the hearts of communities in Indiana, Kentucky, and Florida. His role as the Director of Admissions at prestigious institutions like IMG Academy in Bradenton and KCD in Louisville allowed him to be a "connector and protector" with integrity and charisma.

A proud alumnus of Wabash College and Purdue University, Jeff decided to join the world of real estate after witnessing Shandra's successful transition. He earned his real estate license in 2020 and now works alongside Shandra full time, helping numerous families with their real estate needs.

Jeff and Shandra have found a new love for vacation rental management through their own investment in Bradenton Beach on Anna Maria Island. As a result, they've grown from their flagship property, Coastal Cheer, to over 10 units in the Anna Maria/West Bradenton area.

The Holbrook family has called Bradenton home since 2017, with their children, Samantha and John, competing at the Division I level in athletics. They cherish their time together, often enjoying the Florida sunshine on the boat at Jewfish Key, shelling at Egmont, or fishing in the mangroves.

It's a Great Day at the Cheerful Coast!!!

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 offers the ideal balance of relaxation and convenience. With trolley stops and the Gulf Drive walkway right outside your door, every adventure begins just steps away.

Relax and unwind on the lanai, where breathtaking water views set the tone for your stay. This quaint condo complex provides a peaceful atmosphere while keeping you close to Bridge Street’s vibrant dining, shopping, and entertainment options. With one reserved parking space and access to the island’s free shuttle, exploring Anna Maria Island is a breeze.

Your second-floor condo (elevator temporarily unavailable) ensures a private and tranquil experience. Guests will enjoy access to the pool and provided beach essentials, including chairs and an umbrella, making every trip to the sand stress-free.

Your local hosts live just three miles away and are always available to assist with any needs or provide insider tips to enhance your stay. Visit our real estate storefront at 119 Bridge Street, just steps from the condo, to say hello or learn more about the area.

Cheerful Oasis is your perfect home base for enjoying the best of Anna Maria Island. Book now and experience the charm of this Bay-to-Beach retreat!

Cheerful Oasis

United States

Florida

Bradenton Beach

Despite an unseasonably cold and somewhat rainy week, we could not have been happier with our stay on Gulf Drive in Bradenton Beach.    It started with the personal service and help we received from Jeff at the time we booked.  On the day we arrived he personally met us at the condo to allow us to enter a few hours early.  The condo itself is in an excellent location within walking distance of multiple restaurants and right across from the beach.  We definitely plan to return and will be renting through Cheerful Rentals.

You can't beat the location of this lovely 2 bedroom condo. Across the street from the beach and an easy walk to many restaurants and shops, we were impressed by how quiet this unit was. A lovely deck overlooks the Bay - a perfect spot for a glass of wine or morning coffee. There is every amenity you could ask for on your vacation! The kitchen has a wide selection of dishes, pots/pans, glasses, cutlery & utensils. Appliances include coffee maker, toaster, air fryer, microwave, convection oven, fridge/freezer and dishwasher. A large size washer and dryer in your unit is so convenient. Soaps for kitchen and laundry were provided! There are lots of big, fluffy towels, 2 full baths (1 walk-in shower, 1 tub) and comfy beds for your stay (2 singles and a king). Lawn chairs and coolers for your days on the beach and TVs in the living room and bedrooms (with streaming and cable!) for rainy days...or use the umbrellas to get to your car or the bus to go in town! It's all here. An absolute gem of a property.

Our second time staying here and we will definitely be back next year !

We had a fantastic stay at this property. The place was spacious, spotless, and exactly as advertised. The beach chairs, an umbrella, and other accessories made our beach days super convenient. The beach was just a short walk away, and the pool was close by as well. The location was perfect and within walking distance of restaurants and everything we needed. The hosts were responsive throughout our stay. We would stay here again and recommend it to anyone looking for a relaxing beach getaway!

Bedroom 1

Bedroom 2

Bedroom 3

THE PARTIES. This Short-Term Rental Agreement (“Agreement”) made on {{reservation_date}} between the following:
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Guest: {{guest_name}} (“Guest”), and
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Host: {{host_name}} (“Host”).
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THE PREMISES. The Host agrees to lease the described property below to the Guest, and the Guest agrees to rent from the Host:
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Mailing Address: {{address}}
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Hereinafter known as the “Premises.”
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LEASE TERM. The Guest shall be allowed to occupy the Premises starting {{checkin_date}} from {{checkin_time}} and ending {{checkout_date}} at {{checkout_time}} (“Lease Term”).
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QUIET HOURS. Quiet hours begin at 10:00 PM each night and continue until sunrise. Quiet hours consist of no music and keeping all audio at a minimum level out of respect for the surrounding residents.
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OCCUPANTS. The total number of individuals staying on the Premises during the Lease Term shall be a total of {{number_of_guests}} guests.
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If more than the authorized number of guests listed above are found on the Premises, this Agreement will be subject to termination by the Host.
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BOOKING FEES. The Guest shall pay the Host the amount as detailed during the booking process.
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UTILITIES. The Host shall be responsible for all utilities and services to the Premises EXCEPT for the following: None.
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SECURITY DEPOSIT. The Guest shall be obligated to pay the following amounts upon the execution of this Agreement: No Security Deposit Required
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Security Deposit amount as detailed in the booking process. The Security Deposit is for the faithful performance of the Guest under the terms and conditions of this Agreement. The Guest must pay the Security Deposit at the execution of this Agreement. The Security Deposit shall be returned to the Guest within the State's requirements after the end of the Lease Term less any itemized deductions. This Security Deposit shall not be credited towards any Rent unless the Host gives their written consent.
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PETS. The Host does not allow pets: There are no pets allowed on the Premises. If the Guest is found to have pets on the Premises, this Agreement and any Security Deposit shall be forfeited.
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SMOKING POLICY. Smoking on the Premises is prohibited.
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PERSON OF CONTACT. The Host can be contacted at:
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Host’s Name: {{host_name}}
Telephone: 941-322-4337
E-Mail: cheerfulrentalsami@gmail.com
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SUBLETTING. The guest does not have the right to sublet the Premises.
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INSPECTION. The Host has the right to inspect the Premises with prior notice as in accordance with State law. Should the Guest violate any of the terms of this Agreement, the rental period shall be terminated immediately in accordance with State law. The Guest waives all rights to process if they fail to vacate the premises upon termination of the rental period. The Guest shall vacate the Premises at the expiration time and date of this agreement.
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MAINTENANCE AND REPAIRS. The Guest shall maintain the Premises in a good, clean, and ready-to-rent condition and use the Premises only in a careful and lawful manner. The Guest shall leave the Premises in a ready to rent condition at the expiration of this Agreement, defined by the Host as being immediately habitable by the next Guest. The Guest shall pay for maintenance and repairs should the Premises be left in a lesser condition. The Guest agrees that the Host shall deduct costs of said services from any Security Deposit prior to a refund if Guest causes damage to the Premises or its furnishings.
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TRASH. The Guests shall dispose of all waste material generated during the Lease Term under the strict instruction and direction of the Host.
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QUIET ENJOYMENT. The Guest, along with neighbors, shall enjoy each other’s company in a quiet and respectful manner to each other’s enjoyment. The Guest is expected to behave in a civilized manner and shall be good neighbors with any residents of the immediate area. Creating a disturbance of the area by large gatherings or parties shall be grounds for immediate termination of this Agreement.
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HOST’S LIABILITY. The Guest and any of their guests hereby indemnify and hold harmless the Host against any and all claims of personal injury or property damage or loss arising from the use of the Premises regardless of the nature of the accident, injury or loss. The Guest expressly recognizes that any insurance for property damage or loss which the Host may maintain on the property does not cover the personal property of Guest and that Guest should purchase their own insurance for their guests if such coverage is desired.
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ATTORNEY’S FEES. The Guest agrees to pay all reasonable costs, attorney's fees, and expenses that shall be made or incurred by the Host enforcing this agreement.
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USE OF PREMISES. The Guest shall use the Premises for residential use only. The Guest is not authorized to sell products or services on the Premises or conduct any commercial activity.
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ILLEGAL ACTIVITY. The Guest shall use the Premises for legal purposes only. Any other such use that includes but is not limited to illicit drug use, verbal or physical abuse of any person or illegal sexual behavior shall cause immediate termination of this Agreement with no refund of pre-paid Rent.
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POSSESSIONS. Any personal items or possessions that are left on the Premises are not the responsibility of the Host. The Host shall make every reasonable effort to return the item to the Guest. If claims are not made within the State’s required time period or two (2) weeks, whichever is shorter, the Host shall be able to keep such items to sell or for personal use.
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GOVERNING LAW. This Agreement shall be governed and subject to the laws located in the jurisdiction of Premise’s location.

Cheerful Oasis

About The Property

Sleeping Arrangements

Amenities

Reviews

Location

Bradenton Beach, FL 34217

About The Host

It's a Great Day at the Cheerful Coast!!!

Cheerful Rentals is a professional Host

Safety & Inspections

Additional Details

Cancellation Policy