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St. Augustine Holiday Rentals

414 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 101 - 125 of 414
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4 bedroom Vacation Rental Home in St. Augustine - Ocean Front
Home: 4 Bedroom, 3 Bathroom, Sleeps 12
Location: St. Augustine, Florida, United States
Description: Direct Beach Front, 4 BR, 3 Bath, Bonus Room, Pet Friendly, Wifi This home is the first time on a rental program. They say a view is worth a thou...
Rates
$300 - $600 night
$1995 - $3295 week


Pet Friendly   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 6
Location: St. Augustine, Florida, United States
Description: Enjoy a new sport or activity for every day of your stay: bocci, shuffleboard, snorkeling, swimming and more. Ocean Village Club offers activities ...
Rates
$125 - $260 night
$550 - $1195 week


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4 bedroom Vacation Rental Home in St. Augustine
Home: 4 Bedroom, 2.5 Bathroom, Sleeps 9
Location: St. Augustine, Florida, United States
Description: A private heated saltwater pool, 2 balconies, and sleek modern designs await you at Fan-ta-sea, our 2-story house on a quiet street just 2 blocks f...
Rates
$375 - $633 night
$1595 - $3099 week


Pet Friendly   Swimming Pool   High-Speed Internet


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4 bedroom Vacation Rental Home in St. Augustine - Beach Front
Home: 4 Bedroom, 4 Bathroom, Sleeps 10
Location: St. Augustine, Florida, United States
Description: Enjoy exceptional panoramic views from this oceanfront home at Matanzas Inlet. This 4 bedroom, 4 bathroom vintage beach home is situated high on a ...
Rates
$425 - $805 night
$1595 - $4025 week


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3 bedroom Vacation Rental Home in St. Augustine
Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States
Description: A charming beach house nestled in the trees that gets “oohs and ahhs” from the moment you arrive. Pelican Landing Beach Cottage at Crescent Beach n...
Rates
$125 - $288 night
$595 - $1259 week


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean View
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 7
Location: St. Augustine, Florida, United States
Description: From this oceanfront retreat, you have a stunning view of pure white sand, sparkling sea, and blue sky. Come see it for yourself! Everything at Su...
Rates
$175 - $300 night
$995 - $1575 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean View
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: 2 BRs, 2.5 BAs, Sleeps 6, Ocean View Condo, 4 Heated Pools, Wifi Wake to sounds of waves hitting the sand and the feel the cool ocean breeze from ...
Rates
$150 - $250 night
$795 - $1225 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in St. Augustine
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: St. Augustine, Florida, United States
Description: Stretch your vacation dollar while enjoying all the amenities of a gated beachfront resort in Ocean Village Club A16, our pet-friendly, bright and ...
Rates
$95 - $195 night
$395 - $803 week


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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: Gorgeous ocean views from 2 balconies as well as the master bedroom make Coquina 203B, our 2-story condo on Crescent Beach, the perfect place for y...
Rates
$150 - $350 night
$750 - $1715 week


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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: Perfectly sandwiched between the Atlantic Ocean and the Intracoastal Waterway, our beachfront condo is ideal for a picturesque Crescent Beach vacat...
Rates
$150 - $318 night
$695 - $1497 week


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4 bedroom Vacation Rental Home in St. Augustine - Beach Front
Home: 4 Bedroom, 3.5 Bathroom, Sleeps 14
Location: St. Augustine, Florida, United States
Description: Balconies, patios, and decks bring the beautiful outdoors to Four Seasons, our beach front house in St. Augustine. Spectacular ocean views from mos...
Rates
$450 - $800 night
$1895 - $6500 week


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4 bedroom Vacation Rental Home in St. Augustine - Beach Front
Home: 4 Bedroom, 4.5 Bathroom, Sleeps 12
Location: St. Augustine, Florida, United States
Description: Gorgeous views of the ocean and Intracoastal Waterway are yours from every room in Atlantic Angel, our beachfront Mediterranean-style house in St. ...
Rates
$650 - $1495 night
$2695 - $7475 week


Pet Friendly   Swimming Pool   High-Speed Internet


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4 bedroom Vacation Rental Home in St. Augustine - Ocean View
Home: 4 Bedroom, 3.5 Bathroom, Sleeps 14
Location: St. Augustine, Florida, United States
Description: Full Moon, Pet Friendly, 4 BR, 3 1/2 Bath, Private Pool, Ocean View Just about a two minute's walk from the beach, Full Moon is a beautiful, ocean...
Rates
$400 - $500 night
$2500 - $3000 week


Pet Friendly   Non Smoking   Swimming Pool   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine - Ocean View
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Imagine spending your vacation directly on the beach with 2 balconies overlooking the beach, this totally redecorated 2-storey townhouse at Sea Pla...
Rates
$150 - $275 night
$795 - $1495 week


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3 bedroom Vacation Rental Home in St. Augustine
Home: 3 Bedroom, 2.5 Bathroom, Sleeps 10
Location: St. Augustine, Florida, United States
Description: Bermuda Run, Pet Friendly, 3 BR, 2 1/2 Baths, Sleeps 10, Private Pool Located on beautiful Anastasia Island. This luxury pool home is perfect for...
Rates
$300 - $500 night
$1795 - $2795 week


Pet Friendly   Non Smoking   Swimming Pool   High-Speed Internet


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2 bedroom Vacation Rental Condo in St. Augustine - Beach Front
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 5
Location: St. Augustine, Florida, United States
Description: Crescent Beach stretches away for miles in both directions just beyond the balcony of our corner-unit condo, Summerhouse 102. From this oceanfront ...
Rates
$200 - $462 night
$995 - $1959 week


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1 bedroom Vacation Rental Condo in St. Augustine
Condo: 1 Bedroom, 1 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Located in the only secluded marina in St. Augustine, Mariner?s Paradise offers all the amenities that you expect on your vacation away from home. ...
Rates
$126 - $132 night
$890 - $942 week


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2 bedroom Vacation Rental Condo in St. Augustine - Beach Front
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Barefoot Trace, Ground Floor, Beach Front, 2 BR, 2 Bath, Sleeps 6 This condo is pure luxury living right on the beach. The accommodations are top...
Rates
$300 - $300 night
$995 - $1495 week


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2 bedroom Vacation Rental Condo in St. Augustine
Condo: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States
Description: 2 BR, 2 Bath, Bonus Room, Garage, 2 Pools, Wifi, Tempur Pedic Mattresses Beach living doesn't get any easier than at our spacious condo at Villas ...
Rates
$125 - $250 night
$800 - $1200 week


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2 bedroom Vacation Rental Condo in St. Augustine - Beach Front
Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Enjoy panoramic views of the beautiful dunes and beach from the patio and balcony of our 2-storey townhouse at Four Winds I-10. Located oceanfront,...
Rates
$150 - $318 night
$695 - $1497 week


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2 bedroom Vacation Rental Home in St. Augustine
Home: 2 Bedroom, 1 Bathroom, Sleeps 6
Location: St. Augustine, Florida, United States
Description: Discover a tropical oasis 2 blocks from the beach at Atlantic Oasis, a 2nd story house in St. Augustine. This is the lower ground floor level which...
Rates
$175 - $316 night
$795 - $1374 week


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3 bedroom Vacation Rental Condo in St. Augustine - Ocean Front
Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States
Description: Queen of Quail, Direct Beach/Ocean Front, 3 BR, 2 Bath, Upgraded Condo Welcome to the Queen of Quail Hollow that is directly Beach and Ocean Front...
Rates
$200 - $350 night
$995 - $1595 week


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2 bedroom Vacation Rental Condo in St. Augustine
Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: St. Augustine, Florida, United States
Description: Beautifully Decorated 2 BR, Pet Friendly Condo, Pool, Tennis Court Come and enjoy the beach in this affordable condo that sleeps six comfortably. ...
Rates
$100 - $150 night
$495 - $795 week


Pet Friendly   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: Please note these Check-in Day Requirements for this property: Jan 01 2015 - Dec 31 2023 : Saturday check-in required. Saturday check-out required....
Rates
$95 - $260 night
$665 - $1820 week


Non Smoking


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3 bedroom Vacation Rental Home in St. Augustine - Ocean Front
Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: St. Augustine, Florida, United States
Description: Ocean Paradise, Pet Friendly, Ocean Front, 3 BR, 2 Bath Beach House Our Oceanfront home is located in the heart of St. Augustine Beach. With your ...
Rates
$250 - $400 night
$1595 - $2195 week


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Listings 101 - 125 of 414
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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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