Welcome to Caulfield Rentals
Your St. Augustine Home Away from Home
At Caulfield Rentals, we offer more than just a place to stay - we provide the kind of comfort, cleanliness, and care you'd expect from your own home. Our six beautifully maintained 3-bedroom, 2-bath vacation homes - each with six beds - are thoughtfully designed to accommodate families, couples, business travelers, and group getaways of all sizes.
Whether you're visiting St. Augustine, Florida for work, play, or a bit of both, our properties deliver a perfect blend of professional hospitality and personal charm. Expect spacious interiors, modern furnishings, playful yet tasteful themes (like Lighthouse, Beach, and Captain Americana), and loads of thoughtful extras - from video games and smart TVs to fully stocked kitchens and cozy outdoor spaces.
All six homes are located within one mile of each other, making them ideal for reunions or group trips that need multiple rentals. For larger groups: Book West Oasis 1 and 2, or West Oasis 2 and 3 together for expanded sleeping arrangements, two full kitchens, multiple living areas, and private driveways.
- Professionally Managed, Personally Styled
Enjoy the reliability of a professionally managed stay with the warmth and charm of thoughtfully themed homes - clean, comfortable, and full of personality. - Spacious & Flexible Layouts
Each 3-bedroom, 2-bath home comfortably sleeps up to 10 guests with 6 beds—perfect for families, friend groups, business travelers, or couples’ retreats. - Immaculately Clean & Fully Stocked
We go beyond the basics - expect spotless interiors, fresh linens, hotel-quality bedding, stocked kitchens, and smart home amenities for a stress-free stay. - Prime Location in St. Augustine
All five homes are located within 1 mile of each other - ideal for group bookings or travelers who want to be near the beach, historic sites, and dining. - Light Theming with Fun Extras
Each home features a unique, family-friendly theme—like Beach, Lighthouse, or Pirate—that sparks imagination and adds a touch of adventure to your stay. With playful wall art, retro video game consoles, and classic board games, kids can feel like they're on their own vacation adventure from the moment they arrive. - Seamless Self Check-In & Stellar Support
With automated lock codes, smart messaging, and fast guest support, your check-in is effortless—and we’re just a message away if you need us.
Why Book With Us? Clean. Comfortable. Customer-Focused.
Caulfield Rentals is built on the belief that great guest experiences start with great service. From smooth check-ins with automated lock codes to responsive communication and glowing reviews, we make your stay seamless from start to finish.