Ocean to Bay Rentals

05/18/2026

🏡✨ JUST LISTED! New to Ocean to Bay Rentals! ✨🏡

Say hello to our newest St. Pete rental - Sunshine City Retreat! The perfect home base for your summer getaway! ☀️🌴

📍 St. Petersburg, FL
🛏️ 2 Bedrooms + Dedicated Office
🛁 2 Bathrooms
✨ Freshly updated & move-in ready
🚗 Garage + washer/dryer
🌿 Private yard
🛍️ Close to shopping, restaurants & everything along the 4th Street corridor
⚓ Just 5 miles to the St. Pete Pier
🏖️ Only 13 miles to St. Pete Beach
🛶 Next to kayak and paddleboard launch as well as Crisp Park Boat Ramp!

🎉 NEW LISTING SPECIAL — 20% OFF! 🎉
Be one of our first guests and save!

🇺🇸 Memorial Day escape
🎆 July 4th getaway
☀️ Summer fun in St. Pete

Whether you’re planning beach days, downtown adventures, waterfront dining, Rays games, or just some much-needed sunshine, this one checks all the boxes 🌊🍹

📩 Message me for details or book direct before this introductory discount is gone!

Sunshine City Retreat- Minutes to Downtown St Pete

01/16/2026

Click here for some sunshine https://otbvacations.com/en/belleaire-beach-bliss—gulf-front-retreat-w-heated-pool

01/05/2026

⭐️⭐️⭐️⭐️⭐️
This 5-star review means so much!

This guest spent Christmas at St Pete Modern Retreat with his children after losing his wife to breast cancer. Knowing our home provided comfort, peace, and a safe place to make new memories is why we do what we do.

Our rentals mean more. 🌴💛

12/02/2025

✈️ TRAVEL TUESDAY TREAT ✈️

Dreaming of a beach escape? Make it official.
✨ Travel Tuesday only: Enjoy 25% OFF all stays with Ocean to Bay Rentals through May 2026 🌴Must book today by 11:59pm

🏖 Sun-soaked beach condos
🌅 Cozy coastal retreats
🐾 Pet-friendly stays (select homes)

🔖 Use code: TRAVELTUESDAY (all caps)
📅 Valid for new reservations through May 28 2026!
🔗 Book direct at OTBvacations.com

Now booking: snowbird season, spring break escapes, weekend getaways & everything in between.
Your next great escape is just a click away 💛

Home

11/14/2025

Working on rentals from the cutest little place, Perry’s Porch, in the heart of St. Pete ☕️🌿 The perfect spot to help new hosts turn ideas into income!

Thinking about getting into vacation rentals but not sure where to start? I’m offering a FREE 30-minute strategy call for anyone curious about how to break in, from choosing the right market to setting up your first listing.

📩 Email [email protected] to claim your spot!

11/13/2025

✨ St. Pete is showing off again!
Blue skies, 80-degree days, breezy nights… this fall weather has been chef’s kiss and the holidays are right around the corner.

If you’ve been dreaming of trading snow boots for flip-flops, sunrise coffee for beach walks, or crowded malls for waterfront sunsets — this is your sign.

🎄✨ Book your St. Pete holiday getaway now!
Whether you’re looking for a cozy condo steps to the beach, a downtown retreat near the Pier, or a peaceful spot by the pool, I’ve got beautiful options ready for you.

☀️ Expect:
• Perfect warm winter weather
• Endless outdoor dining + festivals
• Bike-friendly neighborhoods
• Gulf sunsets that feel unreal
• Holiday lights on the water

St. Pete is calling… and the sunshine is waiting.
DM me or visit OTBvacations.com to grab your dates before they’re gone! 🌞🏝️

Home

10/27/2025

✨ Thanksgiving at the Beach! ✨
Why settle for turkey at home when you can feast steps from the sand? 🦃🌊

Book our Belleair Beach Bliss Condo (sleeps 6, pets welcome!) for Thanksgiving week and receive a $100 gift card to the famous Columbia Restaurant at Sand Key — Florida’s oldest restaurant family, serving Spanish-Cuban classics since 1905. 🍷🥘

Enjoy their legendary 1905 Salad, roast turkey with a tropical twist, and sunset views that will make this holiday one to remember. 🌅

➡️ Direct book and save at otbvacations.com! https://otbvacations.com/en/belleaire-beach-bliss---gulf-front-retreat-w-heated-pool

📍 Belleair Beach, FL
🐾 Pets welcome | 🌴 Heated pool | 🚶‍♀️10 steps to the sand

Make this Thanksgiving special, sun-soaked, and stress-free! ☀️💛

10/17/2025

☀️ Happy Friday! You could have this view too.

🌴Book here ⬇️⬇️⬇️

https://otbvacations.com/en/belleaire-beach-bliss---gulf-front-retreat-w-heated-pool

10/07/2025

🌊 Now Hiring: Vacation Rental Cleaner – Rehoboth Beach, Delaware 🌊

Ocean to Bay Rentals is looking for a reliable, detail-oriented cleaner or cleaning team to join our award-winning hospitality company!

Requirements:
• Must be available weekends and able to handle occasional short-notice cleans
• Experience with vacation rental or Airbnb turnarounds preferred
• Dependable transportation and great communication

We Offer:
• Excellent pay and fair compensation for every job
• Bonuses for 5-star cleaning reviews
• Year-round cleanings at multiple properties in Rehoboth Beach
• Steady partnership with a trusted, locally owned company

If you take pride in your work and want to join a growing, top-rated management company, we’d love to hear from you!

📧 Apply or refer someone by emailing: [email protected]
💙 Ocean to Bay Rentals – “Boutique homes. 5-star experiences.”

10/05/2025

✨ Escape the Cold — Spend the Holidays in Key West!☀️🎄

Dreaming of sunshine instead of snow? Key West is calling! 🏝️ Enjoy 20% OFF stays in December & January when you book by October 31st🌞

✈️ With direct flights into the new Key West airport, it’s never been easier to get here — and once you do, there’s so much to enjoy:
• Stroll down Duval Street and take in the festive lights and local charm 🎅
• Watch the sunset at Mallory Square with live music and street performers 🌅
• Go snorkeling or sailing on the crystal-clear turquoise waters 🐠
• Visit Hemingway’s House or take a selfie at the Southernmost Point 📸
• Sip a Key Lime martini while wearing flip-flops instead of snow boots 🍸

Skip the booking fees — book direct at OTBvacations.com and save even more!

🏖️ Paradise is waiting… are you ready?