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St. Augustine Holiday Rentals

497 St. Augustine Holiday Rentals were found matching your criteria.


Featured
$250 - $250 /night
$1160 - $1695 /week
Ocean Front Ground Floor, Wifi, Beach Front Pool - Weekly...

  9 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States


Featured
$167 - $350 /night
$1100 - $1750 /week
Surf View, 3 Bedroom, 2 Bath, Ocean View Home

  3 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States


$125 - $350 /night
$795 - $1195 /week
Ocean/Beach Front Condo at Four Winds, Flat Screens, Wifi...

  2 reviews   Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$66 - $195 /night
$395 - $795 /week
Beacher's Lodge 234, Studio, Pool, Sleeps 4

  4 reviews   Add to Favorites

Condo: Studio, 1 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States


$121 - $425 /night
$850 - $1795 /week
Windjammer 207, 2 Bedrooms, Ocean Front, Pool, Elevator, ...

  18 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$416 - $1380 /night
$2495 - $6325 /week
Dolphin View, 4 Bedroom, Ocean Front, Private Pool, Pet F...

  5 reviews   Add to Favorites

Home: 4 Bedroom, 3 Bathroom, Sleeps 12
Location: St. Augustine, Florida, United States


$90 - $200 /night
$495 - $795 /week
Ocean Front, 1 Bedroom Studio Condo, Wifi

Condo: Studio, 1 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States


$92 - $250 /night
$550 - $1195 /week
Ocean Village Club I33, 2 Bedrooms, Heated Pool, Pet Frie...

  23 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$166 - $430 /night
$995 - $1822 /week
Summerhouse 102, 2 Bedrooms, Ocean Front, Corner Unit, Po...

  25 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 5
Location: St. Augustine, Florida, United States


$150 - $300 /night
$895 - $1650 /week
Colony Reef 2212, 3 BRs, Sleeps 10, Steps to Beach, 2 Poo...

  4 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States


$180 - $295 /night
$945 - $1540 /week
Tradewinds 24

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$110 - $200 /night
$550 - $895 /week
Ocean Village Club L21, 2 Bedroom, 2 Bath, Pet Friendly

  11 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$200 - $450 /night
$1195 - $2495 /week
Sunset Harbor, 3 BR, 2 Bath, Private Pool, Hot Tub, Pet F...

  15 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 12
Location: St. Augustine, Florida, United States


$92 - $250 /night
$550 - $1195 /week
Ocean Village Club E12, Ground Floor, pools, tennis & bea...

  28 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States


$366 - $1150 /night
$2195 - $5750 /week
Golden Sands, 5 Bedrooms, Ocean Views, Private Pool, Spa,...

  8 reviews   Add to Favorites

Home: 5 Bedroom, 3 Bathroom, Sleeps 14
Location: St. Augustine, Florida, United States


$99 - $275 /night
$595 - $1295 /week
Ocean Village Club Q23, 2 Bedrooms, Ocean View, Pet Frien...

  15 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$121 - $425 /night
$850 - $1795 /week
Coquina A 214, 2 Bedrooms, Ocean Front, Pool, Wifi, Sleeps 6

  31 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$299 - $800 /night
$1795 - $4250 /week
Coastal View, 4 Bedrooms, Ocean View, Pet Friendly, Sleep...

  1 reviews   Add to Favorites

Home: 4 Bedroom, 4 Bathroom, Sleeps 10
Location: St. Augustine, Florida, United States


$295 - $445 /night
$1785 - $2380 /week
Surf Side

Home: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States


$125 - $300 /night
$595 - $1300 /week
Summerhouse, Ocean View - Ground Floor - 2 BR, 2 Bath, Wi...

  3 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$116 - $300 /night
$695 - $1395 /week
Hibiscus 201-D, 2 Bedrooms, Ocean View, 3 Pools, Tennis, ...

  12 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$125 - $325 /night
$750 - $1500 /week
Summerhouse 408, 2 Bedrooms, Ocean Front, 4 Heated Pools,...

  14 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$95 - $150 /night
$450 - $875 /week
Pelican Inlet F137, Ground Floor Condo, Boat Parking, Poo...

  3 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States


$116 - $300 /night
$695 - $1395 /week
Colony Reef 3302, 3 Bedrooms, Ocean View, 3rd floor, Indo...

  23 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 7
Location: St. Augustine, Florida, United States


$79 - $225 /night
$550 - $1195 /week
Island House E 225, 2 Bedrooms, Ocean View, Pool, Tennis,...

  9 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States


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.

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