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!!!

NEW LISTING! Welcome to Bay Dream Believer, your luxurious bayfront escape on beautiful Longboat Key! This bright and beautifully upgraded condo offers breathtaking views of Sarasota Bay through massive picture windows and an enclosed patio that lets you soak in the scenery year-round. Located just across the street from public beach access, this property perfectly blends bayfront tranquility with beachside convenience.

Inside, you’ll find a completely refreshed interior featuring high-end finishes, stylish coastal décor, and a spacious open-concept layout ideal for relaxing or entertaining. The fully equipped kitchen includes modern appliances and everything you need to enjoy meals at home, while the comfortable living and dining areas are framed by floor-to-ceiling water views.

Unwind in either of the two inviting bedrooms, both designed with your comfort in mind. The primary suite offers a peaceful retreat with beautiful bay views, while the guest room provides flexibility for family or friends. The enclosed patio is the perfect place to start your morning with coffee or end your evening watching the boats drift by.

Guests of Bay Dream Believer enjoy access to an exceptional array of community amenities, including two heated pools, convenient elevator access, a fitness center, tennis and pickleball courts, and beautifully maintained walking areas along the bay. With pet-friendly accommodations (upon approval) and reserved parking, every detail has been designed to make your stay effortless.

Whether you’re here to relax by the water, explore the pristine beaches of Longboat Key, or visit nearby St. Armands Circle and Anna Maria Island, Bay Dream Believer offers the perfect combination of comfort, location, and coastal style.

Come experience why Longboat Key is one of Florida’s most peaceful and picturesque destinations — and make your next stay one to remember at Bay Dream Believer.

30 DAY MINIMUM STAY - PLEASE CALL FOR LONGER TERM DISCOUNTS OR ANY QUESTIONS!

*All bookings are subject to HOA approval that will include background checks. Minimum of 15 days advance notice for booking.

Bay Dream Believer

Longboat Key

United States

Florida

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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Unless prior approval in writing: 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.&nbsp;
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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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PETS. The Host does allow pets by approval only. Any damage caused by pets will be charged to Guest.
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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: {{host_phone}}
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.&nbsp;
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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.

Bay Dream Believer

About The Property

Sleeping Arrangements

Amenities

Location

Longboat Key, FL 34228

About The Host

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

Cheerful Rentals is a professional Host

Safety & Inspections

Additional Details

Cancellation Policy