Stunning New Property! Welcome to Fullerwood!
39 East Park
Completely Updated
Completely Updated
Perfect for family vacations, group retreats, and extended stays, these luxury vacation rentals in St Augustine, FL are completely updated with comfort and style in mind, featuring 3 master bedrooms and baths. Step outside and experience true resort-style living as you enjoy the private pool and hot tub, and unwind in the expansive outdoo
Perfect for family vacations, group retreats, and extended stays, these luxury vacation rentals in St Augustine, FL are completely updated with comfort and style in mind, featuring 3 master bedrooms and baths. Step outside and experience true resort-style living as you enjoy the private pool and hot tub, and unwind in the expansive outdoor lounge areas. Discover why St Augustine luxury rentals are the ideal choice for your next getaway!
Completely Updated
Completely Updated
Completely Updated
Enjoy a modern kitchen fully equipped for all your cooking needs in one of the best luxury vacation rentals in St. Augustine, FL. After preparing your meals, sit back and relax in one of the several outdoor entertaining spaces. Savor a cup of coffee poolside in the morning, then head upstairs to the outdoor patio for a nightcap, the perfe
Enjoy a modern kitchen fully equipped for all your cooking needs in one of the best luxury vacation rentals in St. Augustine, FL. After preparing your meals, sit back and relax in one of the several outdoor entertaining spaces. Savor a cup of coffee poolside in the morning, then head upstairs to the outdoor patio for a nightcap, the perfect way to end your day at these St. Augustine luxury vacation rentals.
Pool and Hot Tub
Completely Updated
Pool and Hot Tub
This fantastic property is perfect for wedding groups, large families, or couples seeking some privacy. Located just one minute from downtown St Augustine, it's an ideal choice among luxury vacation rentals in St Augustine, FL. Enjoy nearby attractions like the Lightner Museum and the Bridge of Lions, making it one of the top St Augustine luxury rentals for your next retreat.
Ocean Front Property!
Light House Together
Perfect for family vacations, group retreats, and extended stays, these luxury vacation rentals in St Augustine, FL are completely updated with comfort and style in mind, featuring 3 master bedrooms and baths. Step outside and experience true resort-style living as you enjoy the private pool and hot tub, and unwind in the expansive outdoor lounge areas. Discover why St Augustine luxury rentals are the ideal choice for your next getaway!
Light House A
Enjoy a modern kitchen fully equipped for all your cooking needs in one of the best luxury vacation rentals in St. Augustine, FL. After preparing your meals, sit back and relax in one of the several outdoor entertaining spaces. Savor a cup of coffee poolside in the morning, then head upstairs to the outdoor patio for a nightcap, the perfect way to end your day at these St. Augustine luxury vacation rentals.
Light House B
This fantastic property is perfect for wedding groups, large families, or couples seeking some privacy. Located just one minute from downtown St Augustine, it's an ideal choice among luxury vacation rentals in St Augustine, FL. Enjoy nearby attractions like the Lightner Museum and the Bridge of Lions, making it one of the top St Augustine luxury rentals for your next retreat.
STUNNING NEW BEACH PROPERTY! WELCOME TO FLAGLER BEACH HOUSE
Flagler Beach House
Perfect for family vacations, group retreats, and extended stays, these luxury vacation rentals in St Augustine, FL are completely updated with comfort and style in mind, featuring 3 master bedrooms and baths. Step outside and experience true resort-style living as you enjoy the private pool and hot tub, and unwind in the expansive outdoor lounge areas. Discover why St Augustine luxury rentals are the ideal choice for your next getaway!
Blue Heron on May
A rare coastal gem near Vilano Beach—and just 1.1 miles from the sandy shoreline. Tucked away minutes from historic St. Augustine, this home offers the relaxed, walk-to-the-beach lifestyle so many visitors dream of. When you’re searching for a weekend escape, or a longer stay, this is the perfect home. Inside, you’ll find a bright and airy 3-bedroom, 2.5-bath layout designed for both everyday comfort and effortless entertaining. The open-concept living space flows beautifully into the kitchen, featuring upgraded cabinetry, dual pantries, and plenty of storage—perfect for hosting family and friends. Step outside and soak in the coastal vibes from multiple covered balconies, including a private upper-level balcony off the primary suite—an ideal spot for morning coffee or winding down after a day at the beach. The fully fenced, low-maintenance courtyard offers a private outdoor retreat, perfect for grilling, gathering, or simply relaxing in the sea breeze.
Stunning Beach Views!
Enjoy a modern kitchen fully equipped for all your cooking needs in one of the best luxury vacation rentals in St. Augustine, FL. After preparing your meals, sit back and relax in one of the several outdoor entertaining spaces. Savor a cup of coffee poolside in the morning, then head upstairs to the outdoor patio for a nightcap, the perfect way to end your day at these St. Augustine luxury vacation rentals.
DeHaven
This fantastic property is perfect for wedding groups, large families, or couples seeking some privacy. Located just one minute from downtown St Augustine, it's an ideal choice among luxury vacation rentals in St Augustine, FL. Enjoy nearby attractions like the Lightner Museum and the Bridge of Lions, making it one of the top St Augustine luxury rentals for your next retreat.
Coronado
Escape to this charming 3 bedroom 3 bath vacation retreats, perfectly located near beautiful beaches, dowtown attractions dining and year round events. Designed for relation and connection, the home features spacious indoor and outdoor living areas, including a private backyard ideal for entertaining, dining al fresco or unwinding after a day of exploring.
Saragossa
Perfect for family vacations, group retreats, and extended stays, these luxury vacation rentals in St Augustine, FL are completely updated with comfort and style in mind, featuring 3 master bedrooms and baths. Step outside and experience true resort-style living as you enjoy the private pool and hot tub, and unwind in the expansive outdoor lounge areas. Discover why St Augustine luxury rentals are the ideal choice for your next getaway!
Sevilla
Enjoy a modern kitchen fully equipped for all your cooking needs in one of the best luxury vacation rentals in St. Augustine, FL. After preparing your meals, sit back and relax in one of the several outdoor entertaining spaces. Savor a cup of coffee poolside in the morning, then head upstairs to the outdoor patio for a nightcap, the perfect way to end your day at these St. Augustine luxury vacation rentals.
Fullerwood
This fantastic property is perfect for wedding groups, large families, or couples seeking some privacy. Located just one minute from downtown St Augustine, it's an ideal choice among luxury vacation rentals in St Augustine, FL. Enjoy nearby attractions like the Lightner Museum and the Bridge of Lions, making it one of the top St Augustine luxury rentals for your next retreat.
Florence's Cottage and Pool House
Discover a beautiful cottage in the heart of St Augustine, one of the premier luxury vacation rentals in St Augustine, FL. This charming retreat allows you to walk to all that St Augustine has to offer, including delightful restaurants, unique shops, and exciting attractions. Just down the street from the historic Castillo de San Marco, this property features a main house with 2 bedrooms and 2 baths, along with an enclosed back porch that is perfect for watching the kids in the heated pool. The Pool House is a standout feature among St Augustine luxury rentals; it includes a cozy 1 bedroom with a queen-sized bed, a full bath, and a small mini kitchen. This space is ideal for another couple or grandparents looking for a relaxing getaway in one of the best St Augustine luxury vacation rentals.
Heron on May
Coming Soon!
The Heron on May is Perfect for family vacations, group retreats, and extended stays. This luxury vacation rental in St Augustine, FL is completely updated with comfort and style in mind, featuring 3 bedrooms and baths. Step outside and experience true resort-style living as you enjoy the private backyard with grill, unwind in the outdoor lounge areas. Discover why St Augustine luxury rentals are the ideal choice for your next getaway!
Heron on May
This fantastic property is perfect for families or couples seeking some privacy. Located on May Street, enjoy nearby attractions and beaches.
BOOKINGS OPEN JULY 1, 2026
Pool, Beach and Pet friendly!
Koko Vacation Rental
Perfect for family vacations, group retreats, and extended stays, these luxury vacation rentals in St Augustine, FL are completely updated with comfort and style in mind, featuring 3 master bedrooms and baths. Step outside and experience true resort-style living as you enjoy the private pool and hot tub, and unwind in the expansive outdoor lounge areas. Discover why St Augustine luxury rentals are the ideal choice for your next getaway!
Koko Amenities
Enjoy a modern kitchen fully equipped for all your cooking needs in one of the best luxury vacation rentals in St. Augustine, FL. After preparing your meals, sit back and relax in one of the several outdoor entertaining spaces. Savor a cup of coffee poolside in the morning, then head upstairs to the outdoor patio for a nightcap, the perfect way to end your day at these St. Augustine luxury vacation rentals.
Koko Vacation Rental
This fantastic property is perfect for wedding groups, large families, or couples seeking some privacy. Located just one minute from downtown St Augustine, it's an ideal choice among luxury vacation rentals in St Augustine, FL. Enjoy nearby attractions like the Lightner Museum and the Bridge of Lions, making it one of the top St Augustine luxury rentals for your next retreat.
Sea Side 301
Perfect for family vacations, group retreats, and extended stays, these luxury vacation rentals in St Augustine, FL are completely updated with comfort and style in mind, featuring 3 master bedrooms and baths. Step outside and experience true resort-style living as you enjoy the private pool and hot tub, and unwind in the expansive outdoor lounge areas. Discover why St Augustine luxury rentals are the ideal choice for your next getaway!
Sea Side 205
Enjoy a modern kitchen fully equipped for all your cooking needs in one of the best luxury vacation rentals in St. Augustine, FL. After preparing your meals, sit back and relax in one of the several outdoor entertaining spaces. Savor a cup of coffee poolside in the morning, then head upstairs to the outdoor patio for a nightcap, the perfect way to end your day at these St. Augustine luxury vacation rentals.
FLAGER PAD
This fantastic property is perfect for wedding groups, large families, or couples seeking some privacy. Located just one minute from downtown St Augustine, it's an ideal choice among luxury vacation rentals in St Augustine, FL. Enjoy nearby attractions like the Lightner Museum and the Bridge of Lions, making it one of the top St Augustine luxury rentals for your next retreat.
22 1/2 Cincinnati
Tucked away on Cincinnati Street in the historic St Augustine, this charming two bed/bath short term rental offers the perfect blend of comfort, character and location! Enjoy a cozy open concept kitchen and living areas are designed for relaxing after a day of exploring downtown St George street or one of our local pristine beaches. Just a short walk to restaurants, shops and historic attractions, this inviting getaway puts the best of St Augustine right to your door step!
Sweet Uptown
Discover a beautiful cottage in the heart of St Augustine, one of the premier luxury vacation rentals in St Augustine, FL. This charming retreat allows you to walk to all that St Augustine has to offer, including delightful restaurants, unique shops, and exciting attractions. Just down the street from the historic Castillo de San Marco, this property features a main house with 2 bedrooms and 2 baths, along with an enclosed back porch that is perfect for watching the kids in the heated pool. The Pool House is a standout feature among St Augustine luxury rentals; it includes a cozy 1 bedroom with a queen-sized bed, a full bath, and a small mini kitchen. This space is ideal for another couple or grandparents looking for a relaxing getaway in one of the best St Augustine luxury vacation rentals.