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St. Augustine Holiday Rentals

287 St. Augustine Holiday Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within St. Augustine, NE Atlantic Coast, Florida, United States.
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NE Atlantic Coast Top Cities
Listings 51 - 75 of 287
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3 bedroom Vacation Rental Condo in St. Augustine
Condo: 3 Bedroom, 2 Bathroom, Sleeps 10
Location: St. Augustine, Florida, United States
Description: Colony Reef 3103, Ground Floor, 3 BRs, Heated Pool, St Augustine The Atlantic Ocean is just steps away at Colony Reef 3103, our oceanfront ground-... Learn More
Rates
$121 - $250 night
$595 - $1395 week


Non Smoking   High-Speed Internet


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5 bedroom Vacation Rental Home in St. Augustine - Beach Front
Home: 5 Bedroom, 5 Bathroom, Sleeps 16
Location: St. Augustine, Florida, United States
Description: Get ready to experience the perfect vacation, spending every day enjoying spectacular views and all the luxuries of a beautiful beachfront home! G... Learn More
Rates
$316 - $1000 night
$1495 - $4071 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Ocean Village Club P16, Ground Floor Unit, with Wifi, Hdtv, 2 pools, You'll feel as though you're living on a cloud in our light-as-air condo at O... Learn More
Rates
$142 - $142 night
$338 - $1095 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean Front
Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Summerhouse 459 Ocean Front, 2nd & 3rd Floor Ocean Front, 42" Hdtv, Blue Ray Play in the perfect weather of Florida every day with 4 heated pools,... Learn More
Rates
$148 - $300 night
$750 - $1595 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in St. Augustine - Ocean View
Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States
Description: Colony Reef 3404 , 3 BRs, heated indoor pool, 32" Hdtv, Hbo, Wifi Newly updated and repainted as of June 2013. With the advantages of both a quiet... Learn More
Rates
$150 - $350 night
$624 - $1495 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in St. Augustine - Ocean View
Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: The ocean is right outside your window and beneath your breezy balcony when you stay at Sand Dollar II 207, our 2nd-floor beachfront condo on Cresc... Learn More
Rates
$249 - $249 night
$583 - $1795 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean Front
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Island South 11, Ocean Front, Hdtv, Wifi, Penthouse 3rd Floor Newly remodeled and so luxurious, our penthouse condo at Island South 11 overlooks b... Learn More
Rates
$150 - $325 night
$795 - $1695 week


Non Smoking   High-Speed Internet


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4 bedroom Vacation Rental Home in St. Augustine - Ocean Front
Home: 4 Bedroom, 4 Bathroom, Sleeps 12
Location: St. Augustine, Florida, United States
Description: Imagine spending a relaxing ocean front on beautiful Crescent Beach in historic St. Augustine! The upstairs two floors of Gloria Beach House provi... Learn More
Rates
$249 - $1000 night
$1395 - $3495 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: A beach vacation should be as fun and easy as a summer day, and when you stay at our ground-floor condo at Ocean & Racquet 3107, the good life is w... Learn More
Rates
$85 - $150 night
$366 - $695 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Home in St. Augustine
Home: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States
Description: Cranberry Cottage, Private Pool, 100 steps to beach, 2+ BRs, sleeps 8 Just 100 steps from the beach, our upgraded Cranberry Cottage is the perfect... Learn More
Rates
$199 - $400 night
$793 - $1971 week


Pet Friendly   Non Smoking   Swimming Pool   High-Speed Internet


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2 bedroom Vacation Rental Home in St. Augustine
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Blue Bell Cottage pet friendly 2 BRs in historic St Augustine Florida Experience downtown St. Augustine like a native in our charmingly updated Bl... Learn More
Rates
$133 - $133 night
$474 - $900 week


Pet Friendly   Non Smoking   High-Speed Internet


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4 bedroom Vacation Rental Home in St. Augustine
Home: 4 Bedroom, 4 Bathroom, Sleeps 10
Location: St. Augustine, Florida, United States
Description: Bella Rosa is a waterfront castle, complete with boat dock, on the Intracoastal Waterway. Boasting views of the ocean and Matanzas River, this 3-st... Learn More
Rates
$299 - $299 night
$699 - $1995 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean Front
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Four Winds A-3T, 2 Floors - Ocean Front, 2 BRs, 2 heated pools Enjoy panoramic views of the beautiful dunes and beach from the patio and balcony o... Learn More
Rates
$121 - $250 night
$595 - $1400 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Home in St. Augustine
Home: 2 Bedroom, 1 Bathroom, Sleeps 7
Location: St. Augustine, Florida, United States
Description: St Augustine Artist Retreat in Summer Haven, 3 houses to beach! Kick back in historic Summer Haven in our vintage cottage, Artist Retreat. Just 3 ... Learn More
Rates
$116 - $200 night
$499 - $1114 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Be among the very first to enjoy our brand-new 2-storey townhouse at the Villas of Ocean Gate 357. Located in a new complex with 2 swimming pools, ... Learn More
Rates
$167 - $167 night
$519 - $1195 week


Non Smoking   High-Speed Internet


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5 bedroom Vacation Rental Home in St. Augustine
Home: 5 Bedroom, 4 Bathroom, Sleeps 10
Location: St. Augustine, Florida, United States
Description: St Augustine Cordova Mansion with Heated Pool, Spa in Historic St Augustine Step into history in our Spanish-style mansion in the heart of histori... Learn More
Rates
$667 - $1500 night
$4000 - $8286 week


Non Smoking   Swimming Pool   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine
Condo: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Shhh . . . try not to brag about our charming oceanside getaway! Sea Urchin is a well-kept secret, for where else can you vacation just yards from ... Learn More
Rates
$95 - $175 night
$450 - $1000 week


Pet Friendly   Non Smoking


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean Front
Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Surfside Six E - Direct Oceanfront, Luxury, Updated, 2 BRs, Hdtv The beach is your front yard at our townhouse at Surfside Six E! With nothing be... Learn More
Rates
$174 - $250 night
$812 - $1450 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean Front
Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Summerhouse 263, Ocean Front, New Hdtv, Blueray, 4 Heated Pools Spend your next vacation gazing out at the Atlantic Ocean at our beachfront townho... Learn More
Rates
$150 - $325 night
$795 - $1695 week


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1 bedroom Vacation Rental Condo in St. Augustine - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Tucked between Crescent Beach to the east and the Intracoastal Waterway to the west is Beacher's Lodge 425, our ocean front condo with sweeping vie... Learn More
Rates
$100 - $195 night
$495 - $1195 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Quail Hollow A8-3U with pool on Crescent Beach, St Augustine Fl From our light and airy condo at Quail Hollow A8-3U, beautiful Crescent Beach is j... Learn More
Rates
$85 - $150 night
$366 - $695 week


Non Smoking


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3 bedroom Vacation Rental Home in St. Augustine
Home: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: St George Historic House with courtyard in Historic St Augustine Experience St. Augustine's rich history next time you're in town by staying at St... Learn More
Rates
$450 - $450 night
$903 - $2000 week


Non Smoking


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Ocean Village Club K14, Ground Floor unit, 42" Hdtv, Blue Ray, 2 pools From the shaded lanai of our ground-floor condo at Ocean Village Club K14, ... Learn More
Rates
$95 - $175 night
$450 - $1000 week


Non Smoking


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2 bedroom Vacation Rental Condo in St. Augustine
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: From the master bedroom at Hibiscus 101-B, you can see the dunes and the ocean without even leaving the king-sized bed! Our immaculately appointed ... Learn More
Rates
$112 - $225 night
$550 - $1195 week


Non Smoking


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2 bedroom Vacation Rental Condo in St. Augustine
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Everything's just a little newer and nicer at our townhouse at Ocean Club I 34, a mere stone's throw from St. Augustine Beach. Our condo in this oc... Learn More
Rates
$125 - $125 night
$292 - $895 week


Non Smoking


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Listings 51 - 75 of 287
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This map is intended to be used as a reference only.
Please confirm the exact location with the property owner or manager.
 
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.
 

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