As a family-owned business, we deeply value the importance of family and creating lasting memories. At SunnySide Up Rentals, we understand that the right vacation rental can make all the difference in your getaway. That’s why we carefully curate and maintain our properties to ensure a comfortable, stress-free stay—no matter which one you choose.

With years of experience, my husband and I know what it takes to provide top-quality accommodations, and we take pride in delivering exceptional customer service. What sets us apart is our commitment to making every guest feel welcomed, cared for, and valued. Our goal is simple: to provide a 5-STAR experience that turns a great vacation into an unforgettable one.

Have questions before booking? Feel free to email us at sunnysideuprentals@yahoo.com

we look forward to speaking with you. 

12 properties  

$163-465/night Crystal Shores West #503 Sleeps 6
2 bedrooms, 2 baths $200-450/night Crystal Shores West 104 Sleeps 6
2 bedrooms, 2 baths $115-445/night Island Winds West 571 Sleeps 6
2 bedrooms, 2 baths $140-265/night HH B13 Sleeps 6
2 bedrooms, 2 baths $125-350/night HH B23 Sleeps 6
2 bedrooms, 2 baths $167-450/night Tropical Winds Sleeps 6
2 bedrooms, 2 baths $115-400/night Buena Vista #504, Steps to the Beach,1 free parking pass Sleeps 6
2 bedrooms, 2 baths $146-415/night HH B5 Sleeps 7
2 bedrooms, 2 baths (1 full, 1 half) $199-499/night Seawind 901 Sleeps 7
3 bedrooms, 2 baths $152-475/night Stunning Gulf Views, 10th Floor Sleeps 4
2 bedrooms, 2 baths $199-325/night Buena Vista 105 , 1st Floor Sleeps 7
2 bedrooms, 2 baths $100-375/night Harbour Place 401 Sleeps 4
1 bedroom, 2 baths

Please reach out with any questions you may have. We look forward to hosting you and providing a 5-STAR stay!