St. Augustine Vacation Rentals

201 St. Augustine Vacation Rentals were found matching your criteria.

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$325 - $325 /night
$1900 - $1900 /week

Penthouse Villa

Apartment: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: St. Augustine, Florida, United States
Description: Stay on the oldest street in America in this one bedroom villa. Step back into the romance of Old Spain. This villa boasts old world romance from ...

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$325 - $325 /night

$1900 - $1900 /week

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$375 - $375 /night
$1990 - $1990 /week

Penthouse Villa Madrid

Apartment: 1 Bedroom, 1 Bathroom, Sleeps 5
Location: St. Augustine, Florida, United States
Description: Stay on the oldest street in America in this one bedroom villa that can sleep 5 guests. Step back into the romance of Old Spain. This villa boasts...

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$375 - $375 /night

$1990 - $1990 /week

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$228 - $268 /night
$1595 - $1875 /week

5 Star Sand Dollar Condo

Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: NEW 5-STAR LISTING! (SAVE 15%. OWNER OPERATED, SO NO ADMINISTRATIVE FEES.) Treat yourself to the best-kept secret in St. Augustine. It’s Crescent B...

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$228 - $268 /night

$1595 - $1875 /week

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$483 - $1725 /night
$3378 - $12075 /week

Atlantic Dream, Ocean View, 7 Bedrooms, Wrap Around Deck,...

Home: 7 Bedroom, 7 Bathroom, Sleeps 21
Location: St. Augustine, Florida, United States
Description: The name of this property says it all. If you want to enjoy that unforgettable vacation experience, you can do so at Atlantic Dream. You can enjoy ...

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$483 - $1725 /night

$3378 - $12075 /week

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$127 - $351 /night
$889 - $2455 /week

Sea Place Beach House, 3 Bedrooms, Beach Access, 2 Pools,...

2 reviews Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States
Description: Our beach house at Sea Place (remodeled in 2016 kitchen, bathrooms and window treatments) is the perfect combo of convenience and luxury. Just half...

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$127 - $351 /night

$889 - $2455 /week

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$158 - $314 /night
$1108 - $2200 /week

Blue Water Unit B, 2 Bedrooms, Ocean Front, Wifi, Sleeps 6

Home: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States
Description: Blue Water is no ordinary beach house. With its extravagant decks and balconies, this oceanfront 3-story duplex make you feel as if the sands and t...

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$158 - $314 /night

$1108 - $2200 /week

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$125 - $304 /night
$877 - $2126 /week

Ocean Village Club Q35, 2 Bedrooms, Pet Friendly, Wifi, S...

19 reviews Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: A gated condo complex on the shores of the Atlantic, Ocean Village Club has everything you want in a St. Augustine getaway: 2 swimming pools, 2 ten...

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$125 - $304 /night

$877 - $2126 /week

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$102 - $253 /night
$717 - $1770 /week

Sea Place 12128, 2 Bedrooms, Ground Floor, Pool, Wifi, Sl...

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: With 2 bedrooms and 2 bathrooms, Sea Place 12128 is ideal for either 2 couples or a family—or for almost anyone else who wants to vacation only a s...

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$102 - $253 /night

$717 - $1770 /week

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$109 - $278 /night
$766 - $1948 /week

Spyglass 41, 2 Bedrooms, Ocean View, Pool, Wifi, Sleeps 4

18 reviews Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Just because you're at the beach, who says you can't live in luxury? Our three-level condo at SpyGlass 41 is as opulent as a Paris flat, with beaut...

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$109 - $278 /night

$766 - $1948 /week

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$104 - $403 /night
$740 - $2833 /week

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Crescent Beach will be your playground when you stay in Quail Hollow A6-2D, part of a peaceful gated beachside resort near St Augustine, Florida. T...

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$94 - $197 /night

$657 - $1380 /week

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$87 - $202 /night
$606 - $1414 /week

Ocean Village Club A17, 1 Bedroom, Ground Floor, Pet Frie...

35 reviews Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: One of the most affordable vacation spots on choice St. Augustine Beach is Ocean Village Club A17. Our first-floor condo welcomes your family with ...

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$87 - $202 /night

$606 - $1414 /week

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$134 - $329 /night
$937 - $2303 /week

Sea Place 11208, 2 Bedrooms, Ocean Front, Pool, Tennis, W...

57 reviews Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: With 2 balconies overlooking the beach, this totally redecorated 2-storey townhouse at Sea Place 11208 offers you a private view of one of the most...

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$134 - $329 /night

$937 - $2303 /week

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$102 - $253 /night
$717 - $1770 /week

Sea Place 12215, 2 Bedrooms, Ocean View, Pool, Wifi, Slee...

8 reviews Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Great Ocean and pool view townhouse with views of the Ocean. A pretty landscaped entrance awaits at the front of this gated condominium complex. Ta...

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$102 - $253 /night

$717 - $1770 /week

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$134 - $329 /night
$937 - $2303 /week

Colony Reef 2312, 3 Bedrooms, Ocean View, Pool, Tennis, W...

Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: White sand, blue water, and a private balcony beside the ocean. What could be better? This open-concept beachfront condo has everything you need fo...

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$134 - $329 /night

$937 - $2303 /week

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$175 - $362 /night
$1224 - $2535 /week

Sand Dollar I 108, 3 Bedrooms, Ocean Front, Pool, Wifi, S...

20 reviews Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: If our oceanfront condo at Sand Dollar I 108 isn't paradise, it's the nearest place to it! Steps away from Crescent Beach, it also overlooks the dr...

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$175 - $362 /night

$1224 - $2535 /week

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$121 - $233 /night
$846 - $1632 /week

Anastasia Seaside 106, 3 Bedrooms, Pool Access, Wifi, Sle...

Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: The gorgeous sandy beach and the warm Florida sun are calling your name! Anastasia Seaside 106 is a three bedroom, two bathroom condo that sleeps s...

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$121 - $233 /night

$846 - $1632 /week

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$255 - $931 /night
$1782 - $6519 /week

Windswept Sands, 4 Bedroom, Sleeps 11, Ocean front, Pool

Home: 4 Bedroom, 5.5 Bathroom, Sleeps 11
Location: St. Augustine, Florida, United States
Description: The windswept sands of St. Augustine Beach are indeed visible from the balconies of Windswept Sands, a 4-bedroom, 5.5-bathroom retreat mere steps f...

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$255 - $931 /night

$1782 - $6519 /week

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$202 - $431 /night
$1413 - $3018 /week

Windjammer 314, 2 Bedrooms, Ocean Front, Elevator, Pool, ...

37 reviews Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Nestled between the ocean and Intracoastal Waterway, our beachfront condo at Windjammer 314 offers spectacular views of both! Enjoy sunrises and su...

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$202 - $431 /night

$1413 - $3018 /week

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$175 - $362 /night
$1224 - $2535 /week

Windjammer 412, 3 Bedrooms, 4th Floor, Ocean Front, Eleva...

2 reviews Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 7
Location: St. Augustine, Florida, United States
Description: With views of the Atlantic Ocean from one side and those of the Intracoastal Waterway from the other, Windjammer 412 is like a little slice of heav...

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$175 - $362 /night

$1224 - $2535 /week

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St. Augustine Vacation Rentals -- Modern Lodging Concept in America's Oldest City

1513 -- 500 years ago. That's when Juan Ponce de Leon came ashore at what is now St. Augustine, Florida. While there were countless people living in Florida prior to Spanish arrival, the establishment of what would become the first permanent settlement by Europeans in what would become the United States of America was a pretty big deal. Though Ponce obviously had no clue as to the importance of his soggy pants on that day, he must've known he was onto something good when he saw natural harbors, vast expanses of beach (not that they were into sunbathing, but attraction to a beach goes way back in the human psyche), and the potential that was Florida.

Of course, there were no vacation rentals around then. Those came much later -- much, much later. A whole bunch of history happened between Ponce de Leon's arrival and the arrival of air conditioning and the subsequent population of Florida in the 20th century.

Florida vacation rentals have taken off. They’re an ideal way to take in the Sunshine State, and St. Augustine is no different. You can use the oldest city in America as a base to explore some of the nation's new wonders. For example, Disney World and Orlando are less than 2 hours away. Daytona Beach and Jacksonville Beach are even closer. Palm Coast is just down the road.

But we're getting ahead of ourselves. St. Augustine has plenty to see and do all on its own.

The Historic District has the Fountain of Youth Archeological Park featuring a statue of Ponce de Leon himself. You'll see the old city gate and walls, Aviles Street, the oldest public street in the United States. It's from the 16th century--if you're mostly used to your local mall, this will be amazing. You'll find a wonderful mix of art galleries, enjoyable museums, and great places to eat. The Historic District is at the center of the oldest continuous settlement in the United States.

Castillo de San Marcos. Built to ward off attacks from pirates and the British, this fort was completed in 1695. It replaced wooden structures which weren't strong fortifications. It was used as a prisoner of war camp for American soldiers during Revolutionary war. Keep in mind that no pets are allowed in the fort itself. Even with that, it is well worth a visit. You'll find lots of great spots for photo opportunities.

Beaches. Just southeast of the Historic District is Anastasia State Park (you've got to love the name--another nod to history, even if it is Russian history). Florida State Parks are perhaps the best in the United States, and not just because most of them involve a beach. They are well maintained and offer a variety of services. You'll have to pay a small entry fee, but it is well worth it. In all likelihood, you'll have a big beach all to yourself. Similar to Daytona Beach, you can drive on the beach at St. Augustine. You can buy a day pass and access the beach via several access ramps. Keep in mind that there are no beaches in St. Augustine itself--they're just a short drive away, however, and once you find them, you'll have miles and miles of uniterrupted sand and surf.

This map is intended to be used as a reference only.

St. Augustine Vacation Rentals

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