Situated on the east coast of Florida, about an hour south of Jacksonville, the oceanside community St. Augustine is known as the oldest city in the U.S. Not only is this ancient city filled with history, but it also boasts fantastic restaurants and plenty of things to see and do.
Attractions include the Castillo de San Marcos National Monument, St. George Street, the Fountain of Youth, and the Old Jail. This quaint but vibrant city also features art galleries, theaters, live music, and horse-drawn carriages. And then, of course, there are the wide stretches of white sand beaches.
Whether you’re looking for a beachfront condo on St. Augustine Beach, a beach house for a crowd on Anastasia Island, or a cozy bungalow in historic downtown St. Augustine, we’ve found the perfect place to stay on your next visit.
Sure, this spacious oceanfront home costs a pretty penny, but it sleeps up to 22 people, so by the time you split it with friends or family, it’s actually fairly affordable. With a heated saltwater pool, a private boardwalk to beautiful Crescent Beach, a covered lanai, tiki hut, and lawn games like bocce ball, corn hole, and life-size Jenga, this luxury house puts the “vacation” in “vacation home.” Other features include outdoor showers, beach gear, and a game room with foosball and an arcade machine that has 60 games.
Talk about luxury! Sure, this luxurious oceanfront vacation rental costs a couple grand a night and there’s a minimum five-night stay, but how else are you supposed to live your best beach life? This beautifully appointed seaside vacation home boasts amazing ocean views from the balcony of all three bedrooms. A balcony on the south side of the second floor provides breathtaking views of sunrises over the ocean and sunsets over the Intracoastal Waterway.
Crescent Beach is just a short stroll down the private boardwalk. Four beach chairs are provided. This gated property also provides plenty of car and boat parking.
This three-story oceanfront vacation rental has a lot going for it. There’s a heated saltwater private pool on the covered lanai, five decks — including one on the rooftop — a propane fire pit, outdoor games, and each of the five bedrooms is a king suite with its own private bathroom.
Load up the provided beach gear on the beach cart and bring it to the backyard, where you can access the boardwalk that leads directly to the beach! If this beach house is already booked during your desired dates, or your group requires a little more space, this host has another eight-bedroom vacation rental in the area.
Yet another spacious vacation rental in Butler Beach, this four-bedroom beach house sleeps 12. The three-story home features an elevator, so you don’t have to lug your bags up the stairs. St. Augustine Beach is just a couple of minutes away on foot, and historic downtown St. Augustine is 6 miles away.
Just a short walk from St. Augustine Beach, this three-story beach house is quite similar to the one above, except it has a heated pool and fire pit! Grill and chill on the spacious back deck. Play ping pong and outdoor games. Boogie boards, beach towels, and a beach wagon are provided.
Steps from the sand, this four-bedroom beach house is a fantastic retreat for families or multiple couples as it can accommodate up to 12 guests. Sip coffee on one of the upstairs balconies as you watch the sun come up over the water. Beach gear, including a beach cart, boogie boards, and towels, are provided. Watch for wildlife like dolphins and tortoises on the beach. Plenty of restaurants, bars, attractions, and parks can all be found within a few minutes drive.
Tucked away on Anastasia Island’s Butler Beach, this two-bedroom condo boasts both pool and ocean views. Enjoy bike rides on the beach, meals on the balcony, and beautiful sunrises. Historic downtown St. Augustine and great golfing are both just a short drive away.
Just a block from St. Augustine Beach, this duplex unit gives off modern, clean, minimalist vibes. After a day at the beach, rinse off in the outdoor shower. Enjoy meals on the private patio. Beachside restaurants, shops, and a fishing pier are all within walking distance. Downtown Saint Augustine is just a few miles from here.
Planning on packing your pet along on your trip to St. Augustine? This vacation rental in the center of Historic Uptown permits pets for a fee. Part of a five vacation home rental community, this cozy cottage shares a pool and parking with the other five units. Attractions like Castillo De San Marcos and historic St. George Street can be reached on foot in just 5 minutes.
Stay in this sweet cottage that’s nestled beneath a canopy of oak trees draped with Spanish moss. Dine al fresco under the string lights of the pergola and roast marshmallows in the chiminea. This St. Augustine vacation rental is perfect for those who want to explore the historic city. The Fountain of Youth and Old Jail are within a 5-minute walk. Stroll down picturesque Magnolia Avenue. Historic downtown, St. George Street, and the Castillo de San Marcos National Monument are only a mile away. Vilano Beach is less than a couple of miles away, as well, and the rental comes with beach chairs, a beach umbrella, and boogie boards. There are also a couple of bikes and plenty of parking.
Located on beautiful Anastasia Island, this luxurious resort-like rental is giving us major vacation envy. Not only does this stunning Intracoastal Waterway paradise offer amazing panoramic views of sunrises and sunsets on Salt Run across Conch Island, but it also has a pool, hot tub, and its own pier. Watch for dolphins, spotted rays, manatee, osprey, cranes, and more from the dock.
Dozens of fabulous restaurants are within walking distance, including the Conch House Marina Resort. Stroll over the famous Bridge of Lions to reach the restaurants, shops, and bars of historic St. Augustine.
Sporting 3,600 square feet, this luxurious five-bedroom vacation rental is perfect for your next gathering. It’s not on the beach, but it is just right down the street from it, and it’s got a private pool! Kids will enjoy the game/entertainment room, complete with a foosball table. Downtown St. Augustine is just far enough away to enjoy some peace and quiet.
It doesn’t get better on the beach than this tranquil three-story townhome. Enjoy spectacular views of the Atlantic and private access to the uncrowded beach. A paddle board, surfboard, cornhole, bocce ball, fishing poles and bucket, boogie boards, and a cooler are available to rent. Historic downtown St. Augustine is just minutes away.
Between the heated pool, hammock, and outdoor dining area, you could pretty much live in the fenced-in backyard of this Vilano Beach oasis. But you wouldn’t want to with the beach just 50 feet away. Everything you need, including restaurants, a boat launch for fishing, downtown, and attractions like Guana State Park, are within 5 miles of this lovely St. Augustine vacation rental.
How gorgeous is this Vilano Beach vacation rental? Looks aren’t the only thing this two-bedroom home has going for it. Offering panoramic views of the sunrise over the ocean and downtown, and sunsets over the Intracoastal Waterway, its rooftop deck is what vacay dreams are made of. Oh, and there’s a hot tub that overlooks the marsh, plus a dock where you can cast a line for redfish and trout. The beach is just a short walk away, while downtown is just a few miles.
Located in Vilano Beach, this pet-friendly place has a heated pool and a game room with foosball. Plus, it’s just a few minutes from the beach on foot!
Not only does this house have an enclosed heated pool, but it also has a hot tub and comes with a golf cart. What more could you ask for?
Off the A1A, this oceanfront three-bedroom condo can be found within the gated community of Sea Winds. Take advantage of community amenities, including the pool, hot tub, and tennis courts. The private driveway provides parking for one, but visitor parking is available.
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