Welcome to Ocean to Bay Rentals
Where Your Next Coastal Getaway Begins
At Ocean to Bay Rentals, we believe your vacation should be as relaxing as the ocean breeze and as vibrant as a boardwalk sunrise. Whether you're planning a beach week with the family, a romantic escape, or a remote work retreat, our handpicked collection of vacation homes offers something special for every traveler.
Boutique Vacation Stays Curated with Care
Discover handpicked vacation rentals in some of the East Coast’s top destinations — from the family-friendly beaches of Rehoboth Beach, Delaware and the cultural charm of Baltimore, Maryland to the island vibes of Key West and the coastal energy of sunny St. Petersburg, Florida.
Every property we manage is thoughtfully designed, fully equipped, and lovingly maintained to ensure your stay feels like a true escape. Whether you're looking for a family-friendly beach house, a romantic retreat, or a stylish space for remote work and relaxation, we've got you covered.
We’ve been welcoming guests since 2012, and we know that the little things — local recommendations, warm hospitality, and curated interiors — make a big difference.
Your next vacation starts here.
⭐ Superhost on Airbnb
Proudly hosting since 2012, with over 250 five-star reviews and a consistent Superhost rating. Our commitment to exceptional guest experiences and personalized service has earned us a loyal following of happy travelers.
🏆 5-Star Rated on Airbnb & Google
Guests consistently praise our attention to detail, local recommendations, and warm hospitality. “The perfect vacation rental experience — clean, stylish, and stress-free!”
💼 Member of VRMA
As a member of the Vacation Rental Management Association (VRMA), we stay up to date with the highest standards in vacation rental management and guest care.
📣 Special Offer: Book Direct & Save
Skip the service fees! When you book directly through our website, you'll get our lowest available rate — plus early check-in when available.
Featured Properties
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Professional Portraits by Florish Magazine Style Photogrpahy
Professional Real Estate Photography by Gracie Photos Key West
Professional Real Estate Photography by Rick Fensch